TW200418818A - Compounds, compositions, and methods - Google Patents

Info

Publication number

TW200418818A

TW200418818A TW092128029A TW92128029A TW200418818A TW 200418818 A TW200418818 A TW 200418818A TW 092128029 A TW092128029 A TW 092128029A TW 92128029 A TW92128029 A TW 92128029A TW 200418818 A TW200418818 A TW 200418818A

Authority

TW

Taiwan

Prior art keywords

optionally substituted

alkyl

phenyl

substituted

benzyl

Prior art date

2002-10-11

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims description 293
• 239000000203 mixture Substances 0.000 title claims description 60
• 238000000034 method Methods 0.000 title claims description 58
• 230000000694 effects Effects 0.000 claims abstract description 43
• 230000002062 proliferating effect Effects 0.000 claims abstract description 14
• -1 aminofluorenyl Chemical group 0.000 claims description 324
• 125000000217 alkyl group Chemical group 0.000 claims description 179
• 229910052739 hydrogen Inorganic materials 0.000 claims description 98
• 239000001257 hydrogen Substances 0.000 claims description 98
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 77
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 63
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 61
• 125000003107 substituted aryl group Chemical group 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 150000002431 hydrogen Chemical class 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 50
• 230000002079 cooperative effect Effects 0.000 claims description 45
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 43
• 206010028980 Neoplasm Diseases 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000005059 halophenyl group Chemical group 0.000 claims description 24
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 239000000126 substance Substances 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 239000007789 gas Substances 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000002946 cyanobenzyl group Chemical group 0.000 claims description 20
• 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 19
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 15
• 201000010099 disease Diseases 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 229940124531 pharmaceutical excipient Drugs 0.000 claims description 12
• 230000004663 cell proliferation Effects 0.000 claims description 11
• 125000003944 tolyl group Chemical group 0.000 claims description 11
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000004799 bromophenyl group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 4
• 208000006029 Cardiomegaly Diseases 0.000 claims description 4
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 206010020718 hyperplasia Diseases 0.000 claims description 4
• 208000026278 immune system disease Diseases 0.000 claims description 4
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
• 208000037803 restenosis Diseases 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 125000004803 chlorobenzyl group Chemical group 0.000 claims description 3
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 238000002372 labelling Methods 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 108091000080 Phosphotransferase Proteins 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
• 229910052786 argon Inorganic materials 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 102000020233 phosphotransferase Human genes 0.000 claims description 2
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 3
• 125000001207 fluorophenyl group Chemical group 0.000 claims 2
• 239000007983 Tris buffer Substances 0.000 claims 1
• 125000006307 alkoxy benzyl group Chemical group 0.000 claims 1
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
• 101150071577 chi2 gene Chemical group 0.000 claims 1
• 125000000068 chlorophenyl group Chemical group 0.000 claims 1
• 125000006286 dichlorobenzyl group Chemical group 0.000 claims 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
• 150000002460 imidazoles Chemical class 0.000 claims 1
• 150000003949 imides Chemical class 0.000 claims 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
• RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
• 150000002790 naphthalenes Chemical class 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
• 208000015891 sexual disease Diseases 0.000 claims 1
• 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
• MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical class O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 abstract description 2
• 230000001413 cellular effect Effects 0.000 abstract description 2
• 208000037765 diseases and disorders Diseases 0.000 abstract 1
• 238000006243 chemical reaction Methods 0.000 description 80
• 210000004027 cell Anatomy 0.000 description 71
• 239000000243 solution Substances 0.000 description 66
• 239000003795 chemical substances by application Substances 0.000 description 60
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
• 239000002585 base Substances 0.000 description 38
• 239000002253 acid Substances 0.000 description 37
• 229940088597 hormone Drugs 0.000 description 34
• 239000005556 hormone Substances 0.000 description 34
• 150000001412 amines Chemical class 0.000 description 31
• 230000000394 mitotic effect Effects 0.000 description 31
• 238000012360 testing method Methods 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 28
• 239000003814 drug Substances 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• 102000029749 Microtubule Human genes 0.000 description 22
• 230000027455 binding Effects 0.000 description 22
• 210000004688 microtubule Anatomy 0.000 description 22
• 108091022875 Microtubule Proteins 0.000 description 21
• 239000000010 aprotic solvent Substances 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 21
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
• 238000007792 addition Methods 0.000 description 20
• 238000000746 purification Methods 0.000 description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• 229940079593 drug Drugs 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 108090000623 proteins and genes Proteins 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
• 235000018102 proteins Nutrition 0.000 description 17
• 102000004169 proteins and genes Human genes 0.000 description 17
• 239000003112 inhibitor Substances 0.000 description 16
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
• 230000000875 corresponding effect Effects 0.000 description 15
• 230000011278 mitosis Effects 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 230000002401 inhibitory effect Effects 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• 238000010998 test method Methods 0.000 description 13
• 239000002904 solvent Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 125000001188 haloalkyl group Chemical group 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• 108091006112 ATPases Proteins 0.000 description 10
• 102000057290 Adenosine Triphosphatases Human genes 0.000 description 10
• 206010039491 Sarcoma Diseases 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 102000004190 Enzymes Human genes 0.000 description 9
• 108090000790 Enzymes Proteins 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 238000004809 thin layer chromatography Methods 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
• 101001008953 Homo sapiens Kinesin-like protein KIF11 Proteins 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 150000001299 aldehydes Chemical class 0.000 description 8
• 125000005037 alkyl phenyl group Chemical group 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 125000004185 ester group Chemical group 0.000 description 8
• 239000012530 fluid Substances 0.000 description 8
• 239000008103 glucose Substances 0.000 description 8
• 229910052740 iodine Inorganic materials 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 239000003226 mitogen Substances 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 238000012216 screening Methods 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 208000009956 adenocarcinoma Diseases 0.000 description 7
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
• 230000008859 change Effects 0.000 description 7
• 235000019439 ethyl acetate Nutrition 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 206010025323 Lymphomas Diseases 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• 235000011054 acetic acid Nutrition 0.000 description 6
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 6
• 235000001014 amino acid Nutrition 0.000 description 6
• 150000001413 amino acids Chemical class 0.000 description 6
• 230000022131 cell cycle Effects 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 230000006870 function Effects 0.000 description 6
• 102000055595 human KIF11 Human genes 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• 238000000926 separation method Methods 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 description 6
• 238000006467 substitution reaction Methods 0.000 description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 description 5
• 125000005907 alkyl ester group Chemical group 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 230000003833 cell viability Effects 0.000 description 5
• 238000009826 distribution Methods 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 230000002538 fungal effect Effects 0.000 description 5
• 230000003054 hormonal effect Effects 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 125000000468 ketone group Chemical group 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 230000003287 optical effect Effects 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 238000004007 reversed phase HPLC Methods 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 208000017572 squamous cell neoplasm Diseases 0.000 description 5
• 229910052717 sulfur Chemical group 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• 208000003200 Adenoma Diseases 0.000 description 4
• 206010001233 Adenoma benign Diseases 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• 102000004195 Isomerases Human genes 0.000 description 4
• 108090000769 Isomerases Proteins 0.000 description 4
• 229930194542 Keto Natural products 0.000 description 4
• 206010024612 Lipoma Diseases 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• 229940123237 Taxane Drugs 0.000 description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 150000001409 amidines Chemical class 0.000 description 4
• 239000002246 antineoplastic agent Substances 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 235000011089 carbon dioxide Nutrition 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000010949 copper Substances 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 206010016629 fibroma Diseases 0.000 description 4
• 201000011066 hemangioma Diseases 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 230000003993 interaction Effects 0.000 description 4
• 238000001990 intravenous administration Methods 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 238000002955 isolation Methods 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 235000011181 potassium carbonates Nutrition 0.000 description 4
• 108090000765 processed proteins & peptides Proteins 0.000 description 4
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 3
• PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 description 3
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 3
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 101150065749 Churc1 gene Proteins 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 206010018338 Glioma Diseases 0.000 description 3
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 229930012538 Paclitaxel Natural products 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
• 102100038239 Protein Churchill Human genes 0.000 description 3
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 206010043276 Teratoma Diseases 0.000 description 3
• 125000002947 alkylene group Chemical group 0.000 description 3
• 125000006242 amine protecting group Chemical group 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 239000003080 antimitotic agent Substances 0.000 description 3
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 description 3
• 125000004104 aryloxy group Chemical group 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Chemical group 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 230000010261 cell growth Effects 0.000 description 3
• 230000002860 competitive effect Effects 0.000 description 3
• 239000012141 concentrate Substances 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• 229910052802 copper Inorganic materials 0.000 description 3
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 230000004064 dysfunction Effects 0.000 description 3
• 238000005516 engineering process Methods 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• 229910052731 fluorine Inorganic materials 0.000 description 3
• 239000012634 fragment Substances 0.000 description 3
• 238000007306 functionalization reaction Methods 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• 125000005114 heteroarylalkoxy group Chemical group 0.000 description 3
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 3
• 125000002636 imidazolinyl group Chemical group 0.000 description 3
• 239000011261 inert gas Substances 0.000 description 3
• 238000007689 inspection Methods 0.000 description 3
• 201000010260 leiomyoma Diseases 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
• 239000011976 maleic acid Substances 0.000 description 3
• 229940098895 maleic acid Drugs 0.000 description 3
• 238000005259 measurement Methods 0.000 description 3
• 206010027191 meningioma Diseases 0.000 description 3
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 201000008968 osteosarcoma Diseases 0.000 description 3
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
• 229960001592 paclitaxel Drugs 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 239000004810 polytetrafluoroethylene Substances 0.000 description 3
• 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• OZZAYJQNMKMUSD-DMISRAGPSA-N pregnenolone succinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OZZAYJQNMKMUSD-DMISRAGPSA-N 0.000 description 3
• 150000003141 primary amines Chemical class 0.000 description 3
• 125000004076 pyridyl group Chemical group 0.000 description 3
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 3
• 230000009870 specific binding Effects 0.000 description 3
• 230000020347 spindle assembly Effects 0.000 description 3
• 125000005156 substituted alkylene group Chemical group 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
• 150000003512 tertiary amines Chemical class 0.000 description 3
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 3
• 229960000303 topotecan Drugs 0.000 description 3
• 210000004881 tumor cell Anatomy 0.000 description 3
• 230000035899 viability Effects 0.000 description 3
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
• ZKXGQPQAMRSBOL-UHFFFAOYSA-N 1,2,3-trifluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=C(F)C(F)=C2F ZKXGQPQAMRSBOL-UHFFFAOYSA-N 0.000 description 2
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 2
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
• 239000005695 Ammonium acetate Substances 0.000 description 2
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
• 206010007275 Carcinoid tumour Diseases 0.000 description 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 241001635598 Enicostema Species 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 201000008808 Fibrosarcoma Diseases 0.000 description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
• 208000032612 Glial tumor Diseases 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• 102100027629 Kinesin-like protein KIF11 Human genes 0.000 description 2
• 208000018142 Leiomyosarcoma Diseases 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• 206010027626 Milia Diseases 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 208000034578 Multiple myelomas Diseases 0.000 description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
• 201000004404 Neurofibroma Diseases 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
• 229910006074 SO2NH2 Inorganic materials 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 108010090804 Streptavidin Proteins 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
• 208000008383 Wilms tumor Diseases 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
• 125000003282 alkyl amino group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 229910052782 aluminium Inorganic materials 0.000 description 2
• 230000009435 amidation Effects 0.000 description 2
• 238000007112 amidation reaction Methods 0.000 description 2
• 235000019257 ammonium acetate Nutrition 0.000 description 2
• 229940043376 ammonium acetate Drugs 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 239000002518 antifoaming agent Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 238000003491 array Methods 0.000 description 2
• 206010003246 arthritis Diseases 0.000 description 2
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
• 125000005605 benzo group Chemical group 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• 239000004305 biphenyl Substances 0.000 description 2
• 235000010290 biphenyl Nutrition 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 239000001110 calcium chloride Substances 0.000 description 2
• 235000011148 calcium chloride Nutrition 0.000 description 2
• 229910001628 calcium chloride Inorganic materials 0.000 description 2
• 238000004364 calculation method Methods 0.000 description 2
• 244000309466 calf Species 0.000 description 2
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 208000002458 carcinoid tumor Diseases 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 230000030833 cell death Effects 0.000 description 2
• 230000022534 cell killing Effects 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 235000015165 citric acid Nutrition 0.000 description 2
• 238000004140 cleaning Methods 0.000 description 2
• 238000011260 co-administration Methods 0.000 description 2
• 230000009137 competitive binding Effects 0.000 description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 229940127089 cytotoxic agent Drugs 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 238000010494 dissociation reaction Methods 0.000 description 2
• 230000005593 dissociations Effects 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 231100000673 dose–response relationship Toxicity 0.000 description 2
• 239000000975 dye Substances 0.000 description 2
• 239000002532 enzyme inhibitor Substances 0.000 description 2
• 229940125532 enzyme inhibitor Drugs 0.000 description 2
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 239000001530 fumaric acid Substances 0.000 description 2
• 229960002598 fumaric acid Drugs 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• 238000001030 gas--liquid chromatography Methods 0.000 description 2
• 150000004676 glycans Chemical class 0.000 description 2
• 229960004275 glycolic acid Drugs 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 description 2
• 210000005260 human cell Anatomy 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 239000012442 inert solvent Substances 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 229910052742 iron Inorganic materials 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000004811 liquid chromatography Methods 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 230000033001 locomotion Effects 0.000 description 2
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
• 229910001629 magnesium chloride Inorganic materials 0.000 description 2
• FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 2
• 229940107698 malachite green Drugs 0.000 description 2
• 239000001630 malic acid Substances 0.000 description 2
• 235000011090 malic acid Nutrition 0.000 description 2
• 229940099690 malic acid Drugs 0.000 description 2
• 229960002510 mandelic acid Drugs 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 238000002483 medication Methods 0.000 description 2
• 201000001441 melanoma Diseases 0.000 description 2
• 239000012528 membrane Substances 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
• 238000000520 microinjection Methods 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 238000012544 monitoring process Methods 0.000 description 2
• XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 2
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 229930014626 natural product Natural products 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 150000002894 organic compounds Chemical class 0.000 description 2
• 210000001672 ovary Anatomy 0.000 description 2
• 229940116315 oxalic acid Drugs 0.000 description 2
• 235000006408 oxalic acid Nutrition 0.000 description 2
• 229940023569 palmate Drugs 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920001282 polysaccharide Polymers 0.000 description 2
• 239000005017 polysaccharide Substances 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 239000001294 propane Substances 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• 238000001959 radiotherapy Methods 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 229960004889 salicylic acid Drugs 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 238000013207 serial dilution Methods 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 239000008174 sterile solution Substances 0.000 description 2
• 150000008163 sugars Chemical class 0.000 description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 229960001367 tartaric acid Drugs 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 238000012546 transfer Methods 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 229910052722 tritium Inorganic materials 0.000 description 2
• 239000000052 vinegar Substances 0.000 description 2
• 235000021419 vinegar Nutrition 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 239000008215 water for injection Substances 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• 229910052725 zinc Inorganic materials 0.000 description 2
• 239000011701 zinc Substances 0.000 description 2
• CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
• XCAJNBJDLZPHNB-UHFFFAOYSA-N (3-fluoro-4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1F XCAJNBJDLZPHNB-UHFFFAOYSA-N 0.000 description 1
• GCDLQAOATMBBDF-UHFFFAOYSA-N (4-phenylphenyl)methylhydrazine Chemical compound C1=CC(CNN)=CC=C1C1=CC=CC=C1 GCDLQAOATMBBDF-UHFFFAOYSA-N 0.000 description 1
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
• PWQHQNWOXBOOTJ-UHFFFAOYSA-N 3-fluoro-4-methylbenzenecarboximidamide Chemical compound CC1=CC=C(C(N)=N)C=C1F PWQHQNWOXBOOTJ-UHFFFAOYSA-N 0.000 description 1
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
• 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
• UWSONZCNXUSTKW-UHFFFAOYSA-N 4,5-Dimethylthiazole Chemical compound CC=1N=CSC=1C UWSONZCNXUSTKW-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
• UBYXITFNZVIVDW-UHFFFAOYSA-N 4-methylbenzenecarboximidamide Chemical compound CC1=CC=C(C(N)=N)C=C1 UBYXITFNZVIVDW-UHFFFAOYSA-N 0.000 description 1
• PMQXMHYFOSDTLC-UHFFFAOYSA-N 4-methyloctan-1-amine Chemical compound CCCCC(C)CCCN PMQXMHYFOSDTLC-UHFFFAOYSA-N 0.000 description 1
• 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 description 1
• KQROHCSYOGBQGJ-UHFFFAOYSA-N 5-Hydroxytryptophol Chemical compound C1=C(O)C=C2C(CCO)=CNC2=C1 KQROHCSYOGBQGJ-UHFFFAOYSA-N 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 208000023275 Autoimmune disease Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 208000005440 Basal Cell Neoplasms Diseases 0.000 description 1
• 206010004146 Basal cell carcinoma Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 102000004506 Blood Proteins Human genes 0.000 description 1
• 108010017384 Blood Proteins Proteins 0.000 description 1
• 206010073106 Bone giant cell tumour malignant Diseases 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• BYDKOEALTNBRMC-MVSFAKPFSA-N C(C1=CC=CC=C1)O[C@@H]([C@@](C(=O)O)(OCC1=CC=CC=C1)C1=CC=CC=2C3=CC=CC=C3CC12)C(=O)O Chemical compound C(C1=CC=CC=C1)O[C@@H]([C@@](C(=O)O)(OCC1=CC=CC=C1)C1=CC=CC=2C3=CC=CC=C3CC12)C(=O)O BYDKOEALTNBRMC-MVSFAKPFSA-N 0.000 description 1
• LZSWONVBBLNLMF-UHFFFAOYSA-N CCN.N.N.N Chemical compound CCN.N.N.N LZSWONVBBLNLMF-UHFFFAOYSA-N 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
• 244000025254 Cannabis sativa Species 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 102100025832 Centromere-associated protein E Human genes 0.000 description 1
• 206010008263 Cervical dysplasia Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 201000005262 Chondroma Diseases 0.000 description 1
• 208000005243 Chondrosarcoma Diseases 0.000 description 1
• 201000009047 Chordoma Diseases 0.000 description 1
• 208000006332 Choriocarcinoma Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
• IYKIBYRRBSHMRL-UHFFFAOYSA-N Cl[AsH](OCC)=O Chemical compound Cl[AsH](OCC)=O IYKIBYRRBSHMRL-UHFFFAOYSA-N 0.000 description 1
• 206010048832 Colon adenoma Diseases 0.000 description 1
• 208000032170 Congenital Abnormalities Diseases 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical class OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 description 1
• 206010061619 Deformity Diseases 0.000 description 1
• LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
• 241000790917 Dioxys <bee> Species 0.000 description 1
• 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• JFUZLLJNSLALQE-UHFFFAOYSA-N FC1=C(C(=C(C=2CC3=CC=CC=C3C12)S(=O)(=O)O)F)F Chemical compound FC1=C(C(=C(C=2CC3=CC=CC=C3C12)S(=O)(=O)O)F)F JFUZLLJNSLALQE-UHFFFAOYSA-N 0.000 description 1
• RCGHDXVMNKXLJQ-UHFFFAOYSA-N FC1=C(F)C(F)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C12 Chemical compound FC1=C(F)C(F)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C12 RCGHDXVMNKXLJQ-UHFFFAOYSA-N 0.000 description 1
• 208000007659 Fibroadenoma Diseases 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• 229930091371 Fructose Natural products 0.000 description 1
• 239000005715 Fructose Substances 0.000 description 1
• RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
• 208000021309 Germ cell tumor Diseases 0.000 description 1
• 208000007569 Giant Cell Tumors Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 206010019629 Hepatic adenoma Diseases 0.000 description 1
• 206010019695 Hepatic neoplasm Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101001027192 Homo sapiens Kelch-like protein 41 Proteins 0.000 description 1
• 101000605743 Homo sapiens Kinesin-like protein KIF23 Proteins 0.000 description 1
• 101001006776 Homo sapiens Kinesin-like protein KIFC1 Proteins 0.000 description 1
• 102000004867 Hydro-Lyases Human genes 0.000 description 1
• 108090001042 Hydro-Lyases Proteins 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
• 241000692870 Inachis io Species 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 102100037644 Kelch-like protein 41 Human genes 0.000 description 1
• 208000002260 Keloid Diseases 0.000 description 1
• 102100038406 Kinesin-like protein KIF23 Human genes 0.000 description 1
• 102100023424 Kinesin-like protein KIF2C Human genes 0.000 description 1
• 101710134369 Kinesin-like protein KIF2C Proteins 0.000 description 1
• 102100027942 Kinesin-like protein KIFC1 Human genes 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 201000004462 Leydig Cell Tumor Diseases 0.000 description 1
• 208000002404 Liver Cell Adenoma Diseases 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 206010027406 Mesothelioma Diseases 0.000 description 1
• 244000294411 Mirabilis expansa Species 0.000 description 1
• 235000015429 Mirabilis expansa Nutrition 0.000 description 1
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
• 208000014767 Myeloproliferative disease Diseases 0.000 description 1
• 239000007832 Na2SO4 Substances 0.000 description 1
• 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 description 1
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 239000000020 Nitrocellulose Substances 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 239000004677 Nylon Substances 0.000 description 1
• 201000010133 Oligodendroglioma Diseases 0.000 description 1
• 108091034117 Oligonucleotide Proteins 0.000 description 1
• 102000015636 Oligopeptides Human genes 0.000 description 1
• 108010038807 Oligopeptides Proteins 0.000 description 1
• 206010031149 Osteitis Diseases 0.000 description 1
• 208000001715 Osteoblastoma Diseases 0.000 description 1
• 241000237502 Ostreidae Species 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 206010061535 Ovarian neoplasm Diseases 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 102000035195 Peptidases Human genes 0.000 description 1
• 108091005804 Peptidases Proteins 0.000 description 1
• BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
• 208000007641 Pinealoma Diseases 0.000 description 1
• 239000004793 Polystyrene Substances 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 239000004365 Protease Substances 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
• 102000013009 Pyruvate Kinase Human genes 0.000 description 1
• 108020005115 Pyruvate Kinase Proteins 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 241000219061 Rheum Species 0.000 description 1
• 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
• 108091006627 SLC12A9 Proteins 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 102100036742 Solute carrier family 12 member 9 Human genes 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
• 208000024313 Testicular Neoplasms Diseases 0.000 description 1
• 206010057644 Testis cancer Diseases 0.000 description 1
• 229910052776 Thorium Inorganic materials 0.000 description 1
• 206010052779 Transplant rejections Diseases 0.000 description 1
• 241000009298 Trigla lyra Species 0.000 description 1
• 229920004890 Triton X-100 Polymers 0.000 description 1
• 239000013504 Triton X-100 Substances 0.000 description 1
• 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
• 206010046798 Uterine leiomyoma Diseases 0.000 description 1
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
• 206010052428 Wound Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 206010048215 Xanthomatosis Diseases 0.000 description 1
• JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 230000007488 abnormal function Effects 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 239000012042 active reagent Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 125000002015 acyclic group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 229940009456 adriamycin Drugs 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000006177 alkyl benzyl group Chemical group 0.000 description 1
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 238000002399 angioplasty Methods 0.000 description 1
• 230000002927 anti-mitotic effect Effects 0.000 description 1
• 230000001028 anti-proliverative effect Effects 0.000 description 1
• 239000004599 antimicrobial Substances 0.000 description 1
• BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 159000000032 aromatic acids Chemical class 0.000 description 1
• 150000007860 aryl ester derivatives Chemical group 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• 150000003851 azoles Chemical class 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 239000011324 bead Substances 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 238000002306 biochemical method Methods 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 208000018339 bone inflammation disease Diseases 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 201000002143 bronchus adenoma Diseases 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 238000001354 calcination Methods 0.000 description 1
• 229940127093 camptothecin Drugs 0.000 description 1
• 230000004611 cancer cell death Effects 0.000 description 1
• 208000035269 cancer or benign tumor Diseases 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• 210000000845 cartilage Anatomy 0.000 description 1
• 239000005018 casein Substances 0.000 description 1
• BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
• 235000021240 caseins Nutrition 0.000 description 1
• 210000005056 cell body Anatomy 0.000 description 1
• 239000012930 cell culture fluid Substances 0.000 description 1
• 230000032823 cell division Effects 0.000 description 1
• 238000001516 cell proliferation assay Methods 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 210000003850 cellular structure Anatomy 0.000 description 1
• 108010031379 centromere protein E Proteins 0.000 description 1
• 239000013043 chemical agent Substances 0.000 description 1
• 238000010382 chemical cross-linking Methods 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 208000006990 cholangiocarcinoma Diseases 0.000 description 1
• 201000005217 chondroblastoma Diseases 0.000 description 1
• 210000000349 chromosome Anatomy 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 235000017803 cinnamon Nutrition 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 229940100060 combination of electrolytes Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000012258 culturing Methods 0.000 description 1
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical group N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 210000004292 cytoskeleton Anatomy 0.000 description 1
• 230000001086 cytosolic effect Effects 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 238000007405 data analysis Methods 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 239000003599 detergent Substances 0.000 description 1
• 229940119744 dextran 40 Drugs 0.000 description 1
• AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
• 229960003529 diazepam Drugs 0.000 description 1
• DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical class O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• UFMVNSFONAZFOT-UHFFFAOYSA-N dichloromethane;n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound ClCCl.CCN(C(C)C)C(C)C UFMVNSFONAZFOT-UHFFFAOYSA-N 0.000 description 1
• 125000004188 dichlorophenyl group Chemical group 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
• 229960005156 digoxin Drugs 0.000 description 1
• LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
• 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
• 229910001873 dinitrogen Inorganic materials 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 210000005069 ears Anatomy 0.000 description 1
• 230000002275 effect on microtubule Effects 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 229940021013 electrolyte solution Drugs 0.000 description 1
• 239000008151 electrolyte solution Substances 0.000 description 1
• 208000023965 endometrium neoplasm Diseases 0.000 description 1
• 208000023437 ependymal tumor Diseases 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• SSDZYLQUYMOSAK-UHFFFAOYSA-N ethynylcyclohexane Chemical group C#CC1CCCCC1 SSDZYLQUYMOSAK-UHFFFAOYSA-N 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000001125 extrusion Methods 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 230000004992 fission Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 238000000684 flow cytometry Methods 0.000 description 1
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
• 125000005567 fluorenylene group Chemical group 0.000 description 1
• 125000004175 fluorobenzyl group Chemical group 0.000 description 1
• 229960002949 fluorouracil Drugs 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 229940013688 formic acid Drugs 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 229960002737 fructose Drugs 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
• 201000000052 gastrinoma Diseases 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 229960001031 glucose Drugs 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 230000009036 growth inhibition Effects 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 201000005787 hematologic cancer Diseases 0.000 description 1
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
• 208000006359 hepatoblastoma Diseases 0.000 description 1
• 201000002735 hepatocellular adenoma Diseases 0.000 description 1
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 238000003018 immunoassay Methods 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000012750 in vivo screening Methods 0.000 description 1
• 239000005414 inactive ingredient Substances 0.000 description 1
• RLIUKKHIBMHFOK-UHFFFAOYSA-N indium sodium Chemical compound [Na].[In] RLIUKKHIBMHFOK-UHFFFAOYSA-N 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 210000002570 interstitial cell Anatomy 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 230000010189 intracellular transport Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 201000010985 invasive ductal carcinoma Diseases 0.000 description 1
• 229960004903 invert sugar Drugs 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 210000001117 keloid Anatomy 0.000 description 1
• 208000022013 kidney Wilms tumor Diseases 0.000 description 1
• 229940116871 l-lactate Drugs 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 206010024627 liposarcoma Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000002751 lymph Anatomy 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 239000006249 magnetic particle Substances 0.000 description 1
• 230000007257 malfunction Effects 0.000 description 1
• 201000004593 malignant giant cell tumor Diseases 0.000 description 1
• 201000000289 malignant teratoma Diseases 0.000 description 1
• 208000026037 malignant tumor of neck Diseases 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 230000007721 medicinal effect Effects 0.000 description 1
• 230000021121 meiosis Effects 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
• 238000000386 microscopy Methods 0.000 description 1
• 238000010232 migration assay Methods 0.000 description 1
• 235000013336 milk Nutrition 0.000 description 1
• 239000008267 milk Substances 0.000 description 1
• 210000004080 milk Anatomy 0.000 description 1
• 235000013536 miso Nutrition 0.000 description 1
• 230000002297 mitogenic effect Effects 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
• 230000004899 motility Effects 0.000 description 1
• 208000025113 myeloid leukemia Diseases 0.000 description 1
• 208000009091 myxoma Diseases 0.000 description 1
• GINQYTLDMNFGQP-UHFFFAOYSA-N n,n-dimethylformamide;methylsulfinylmethane Chemical compound CS(C)=O.CN(C)C=O GINQYTLDMNFGQP-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000013642 negative control Substances 0.000 description 1
• 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
• 201000008026 nephroblastoma Diseases 0.000 description 1
• 210000005036 nerve Anatomy 0.000 description 1
• 210000004126 nerve fiber Anatomy 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 230000004751 neurological system process Effects 0.000 description 1
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
• BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229920001220 nitrocellulos Polymers 0.000 description 1
• PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 description 1
• 230000036963 noncompetitive effect Effects 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 238000010606 normalization Methods 0.000 description 1
• 238000010899 nucleation Methods 0.000 description 1
• 229920001778 nylon Polymers 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000008184 oral solid dosage form Substances 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 208000003388 osteoid osteoma Diseases 0.000 description 1
• 125000003431 oxalo group Chemical group 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 235000020636 oyster Nutrition 0.000 description 1
• 238000012856 packing Methods 0.000 description 1
• 210000003254 palate Anatomy 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
• WAJUCMNAGKFHLB-UHFFFAOYSA-N phenylarsinic acid Chemical compound O[AsH](=O)C1=CC=CC=C1 WAJUCMNAGKFHLB-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
• 238000003566 phosphorylation assay Methods 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 238000000053 physical method Methods 0.000 description 1
• 208000024724 pineal body neoplasm Diseases 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 210000004508 polar body Anatomy 0.000 description 1
• 229920000151 polyglycol Polymers 0.000 description 1
• 239000010695 polyglycol Substances 0.000 description 1
• 238000006116 polymerization reaction Methods 0.000 description 1
• 108091033319 polynucleotide Proteins 0.000 description 1
• 102000040430 polynucleotide Human genes 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 229920002223 polystyrene Polymers 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 238000004321 preservation Methods 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• IAHIMVFWYADCJJ-UHFFFAOYSA-N prop-1-enylcyclohexane Chemical group CC=CC1CCCCC1 IAHIMVFWYADCJJ-UHFFFAOYSA-N 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 229940095574 propionic acid Drugs 0.000 description 1
• PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940076788 pyruvate Drugs 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 238000000163 radioactive labelling Methods 0.000 description 1
• 239000000941 radioactive substance Substances 0.000 description 1
• 229910052705 radium Inorganic materials 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 238000006268 reductive amination reaction Methods 0.000 description 1
• 230000022983 regulation of cell cycle Effects 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 229910052702 rhenium Inorganic materials 0.000 description 1
• WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229910052701 rubidium Inorganic materials 0.000 description 1
• 210000004116 schwann cell Anatomy 0.000 description 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 235000015170 shellfish Nutrition 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 210000003625 skull Anatomy 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 239000001540 sodium lactate Substances 0.000 description 1
• 235000011088 sodium lactate Nutrition 0.000 description 1
• 229940005581 sodium lactate Drugs 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000002689 soil Substances 0.000 description 1
• 238000000935 solvent evaporation Methods 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 239000008227 sterile water for injection Substances 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 239000004575 stone Chemical group 0.000 description 1
• 150000003440 styrenes Chemical class 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• 229960005137 succinic acid Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 229920002994 synthetic fiber Polymers 0.000 description 1
• 239000012209 synthetic fiber Substances 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• KOTXAHKUCAQPQA-AAUVPWARSA-N taxine Chemical compound C1([C@@H]([C@@H](O)C(=O)O[C@@H]2C=3/C[C@@](C([C@H](O)C4=C(C)[C@@H](OC(C)=O)CC(C4(C)C)[C@@H](OC(C)=O)\C=3)=O)(C)[C@@H](O)C2)N(C)C)=CC=CC=C1 KOTXAHKUCAQPQA-AAUVPWARSA-N 0.000 description 1
• 229930189271 taxine Natural products 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 201000003120 testicular cancer Diseases 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229910052716 thallium Inorganic materials 0.000 description 1
• BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• 208000022271 tubular adenoma Diseases 0.000 description 1
• 208000025421 tumor of uterus Diseases 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000024719 uterine cervix neoplasm Diseases 0.000 description 1
• 210000004291 uterus Anatomy 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• 210000001215 vagina Anatomy 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 230000002227 vasoactive effect Effects 0.000 description 1
• 208000009540 villous adenoma Diseases 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000011179 visual inspection Methods 0.000 description 1
• 210000003905 vulva Anatomy 0.000 description 1