TW308594B - - Google Patents

Info

Publication number

TW308594B

TW308594B TW083109427A TW83109427A TW308594B TW 308594 B TW308594 B TW 308594B TW 083109427 A TW083109427 A TW 083109427A TW 83109427 A TW83109427 A TW 83109427A TW 308594 B TW308594 B TW 308594B

Authority

TW

Taiwan

Prior art keywords

compound

pyridyl

substituted

hexahydropyridyl

formula

Prior art date

1993-10-15

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 claims abstract description 351
• 238000000034 method Methods 0.000 claims abstract description 61
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
• 230000010261 cell growth Effects 0.000 claims abstract description 8
• -1 benzotriazol-1-yloxy Chemical group 0.000 claims description 165
• 238000011049 filling Methods 0.000 claims description 112
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 110
• 125000000217 alkyl group Chemical group 0.000 claims description 90
• 238000006243 chemical reaction Methods 0.000 claims description 71
• 239000000203 mixture Substances 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 210000004027 cell Anatomy 0.000 claims description 52
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 44
• 108090000623 proteins and genes Proteins 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 32
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 239000007789 gas Substances 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 238000006467 substitution reaction Methods 0.000 claims description 16
• 102000004357 Transferases Human genes 0.000 claims description 14
• 108090000992 Transferases Proteins 0.000 claims description 14
• 238000007639 printing Methods 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 13
• 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
• 102000016914 ras Proteins Human genes 0.000 claims description 10
• 108010014186 ras Proteins Proteins 0.000 claims description 10
• 210000004881 tumor cell Anatomy 0.000 claims description 10
• 230000002159 abnormal effect Effects 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• 230000002079 cooperative effect Effects 0.000 claims description 7
• 238000002844 melting Methods 0.000 claims description 7
• 238000012360 testing method Methods 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 230000008018 melting Effects 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 230000012010 growth Effects 0.000 claims description 5
• 150000002500 ions Chemical class 0.000 claims description 5
• 231100000590 oncogenic Toxicity 0.000 claims description 4
• 230000002246 oncogenic effect Effects 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 238000011161 development Methods 0.000 claims description 3
• 238000005516 engineering process Methods 0.000 claims description 3
• 230000002255 enzymatic effect Effects 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 238000012856 packing Methods 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 238000007363 ring formation reaction Methods 0.000 claims description 2
• 230000008961 swelling Effects 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• 230000000007 visual effect Effects 0.000 claims description 2
• 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims 4
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 3
• 238000005481 NMR spectroscopy Methods 0.000 claims 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
• 101150009274 nhr-1 gene Proteins 0.000 claims 2
• WWIKWOJUJQCHIZ-UHFFFAOYSA-N 1-methyl-9h-xanthene Chemical compound O1C2=CC=CC=C2CC2=C1C=CC=C2C WWIKWOJUJQCHIZ-UHFFFAOYSA-N 0.000 claims 1
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims 1
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
• VZUJTDYSGISPLP-UHFFFAOYSA-N 3-pyridin-3-yloxypyridine Chemical compound C=1C=CN=CC=1OC1=CC=CN=C1 VZUJTDYSGISPLP-UHFFFAOYSA-N 0.000 claims 1
• VJVWXXJJQUKUPL-UHFFFAOYSA-N 4-pyridin-4-yloxypyridine Chemical compound C=1C=NC=CC=1OC1=CC=NC=C1 VJVWXXJJQUKUPL-UHFFFAOYSA-N 0.000 claims 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
• 201000009030 Carcinoma Diseases 0.000 claims 1
• 235000005633 Chrysanthemum balsamita Nutrition 0.000 claims 1
• 229940126062 Compound A Drugs 0.000 claims 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
• 206010064571 Gene mutation Diseases 0.000 claims 1
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
• 241000590428 Panacea Species 0.000 claims 1
• 101150111878 Vegfd gene Proteins 0.000 claims 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
• 125000002619 bicyclic group Chemical group 0.000 claims 1
• 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 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 210000002490 intestinal epithelial cell Anatomy 0.000 claims 1
• 208000032839 leukemia Diseases 0.000 claims 1
• 229910052705 radium Inorganic materials 0.000 claims 1
• HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 1
• 108700042226 ras Genes Proteins 0.000 claims 1
• 230000001172 regenerating effect Effects 0.000 claims 1
• 238000001228 spectrum Methods 0.000 claims 1
• 230000000153 supplemental effect Effects 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 6
• 230000008569 process Effects 0.000 abstract description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 107
• 239000000243 solution Substances 0.000 description 102
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• 238000002360 preparation method Methods 0.000 description 44
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 44
• DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 38
• 235000018102 proteins Nutrition 0.000 description 34
• 102000004169 proteins and genes Human genes 0.000 description 34
• 239000000047 product Substances 0.000 description 32
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
• 239000011541 reaction mixture Substances 0.000 description 27
• 239000007787 solid Substances 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
• 239000000460 chlorine Substances 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 18
• 238000012546 transfer Methods 0.000 description 18
• 206010028980 Neoplasm Diseases 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
• 230000005764 inhibitory process Effects 0.000 description 14
• 238000001914 filtration Methods 0.000 description 13
• 239000000523 sample Substances 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 11
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• 235000002639 sodium chloride Nutrition 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 229940125898 compound 5 Drugs 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 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 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 241000283690 Bos taurus Species 0.000 description 7
• 125000003545 alkoxy group Chemical group 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 230000000875 corresponding effect Effects 0.000 description 7
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 230000007062 hydrolysis Effects 0.000 description 7
• 238000006460 hydrolysis reaction Methods 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 201000011510 cancer Diseases 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 238000001514 detection method Methods 0.000 description 6
• 235000011180 diphosphates Nutrition 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 210000005069 ears Anatomy 0.000 description 6
• 238000000855 fermentation Methods 0.000 description 6
• 230000004151 fermentation Effects 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 238000004519 manufacturing process Methods 0.000 description 6
• 229940050176 methyl chloride Drugs 0.000 description 6
• 230000000802 nitrating effect Effects 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 229910052714 tellurium Inorganic materials 0.000 description 6
• PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 6
• 238000004809 thin layer chromatography Methods 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 241000699666 Mus <mouse, genus> Species 0.000 description 5
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 230000000711 cancerogenic effect Effects 0.000 description 5
• 231100000315 carcinogenic Toxicity 0.000 description 5
• 230000008859 change Effects 0.000 description 5
• XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 5
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
• 229910052737 gold Inorganic materials 0.000 description 5
• 239000010931 gold Substances 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• 239000012038 nucleophile Substances 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 239000004033 plastic Substances 0.000 description 5
• 229920003023 plastic Polymers 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 230000002829 reductive effect Effects 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000003981 vehicle Substances 0.000 description 5
• GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• 244000025254 Cannabis sativa Species 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 108700020796 Oncogene Proteins 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• 235000011034 Rubus glaucus Nutrition 0.000 description 4
• 235000009122 Rubus idaeus Nutrition 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 239000012300 argon atmosphere Substances 0.000 description 4
• 125000003710 aryl alkyl group Chemical group 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 210000004556 brain Anatomy 0.000 description 4
• 125000002837 carbocyclic group Chemical group 0.000 description 4
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 235000013305 food Nutrition 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 239000010985 leather Substances 0.000 description 4
• 239000011777 magnesium Substances 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• 239000002609 medium Substances 0.000 description 4
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
• 230000035772 mutation Effects 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• 239000002356 single layer Substances 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• 208000034248 vanishing lung syndrome Diseases 0.000 description 4
• 239000000052 vinegar Substances 0.000 description 4
• 235000021419 vinegar Nutrition 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 206010009944 Colon cancer Diseases 0.000 description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 241000219823 Medicago Species 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• 102000043276 Oncogene Human genes 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 240000007651 Rubus glaucus Species 0.000 description 3
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 229910052770 Uranium Inorganic materials 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• 125000003342 alkenyl group Chemical group 0.000 description 3
• 239000000908 ammonium hydroxide Substances 0.000 description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 230000030944 contact inhibition Effects 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 238000002309 gasification Methods 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 239000007937 lozenge Substances 0.000 description 3
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
• 235000019341 magnesium sulphate Nutrition 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• FXADMRZICBQPQY-UHFFFAOYSA-N orthotelluric acid Chemical compound O[Te](O)(O)(O)(O)O FXADMRZICBQPQY-UHFFFAOYSA-N 0.000 description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000002002 slurry Substances 0.000 description 3
• 238000009331 sowing Methods 0.000 description 3
• 239000011550 stock solution Substances 0.000 description 3
• 239000003930 superacid Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 230000009466 transformation Effects 0.000 description 3
• 239000003039 volatile agent Substances 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical group [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
• LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
• LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• 241001674044 Blattodea Species 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• 208000035484 Cellulite Diseases 0.000 description 2
• 241000282994 Cervidae Species 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• 244000241257 Cucumis melo Species 0.000 description 2
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• 229910002651 NO3 Inorganic materials 0.000 description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
• 240000007594 Oryza sativa Species 0.000 description 2
• 235000007164 Oryza sativa Nutrition 0.000 description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
• 206010049752 Peau d'orange Diseases 0.000 description 2
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
• 229960000583 acetic acid Drugs 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
• 150000004703 alkoxides Chemical class 0.000 description 2
• 150000003973 alkyl amines Chemical class 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 230000001028 anti-proliverative effect Effects 0.000 description 2
• 229910052786 argon Inorganic materials 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 210000000988 bone and bone Anatomy 0.000 description 2
• 229910052796 boron Inorganic materials 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 150000001793 charged compounds Chemical class 0.000 description 2
• 239000012320 chlorinating reagent Substances 0.000 description 2
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
• 229940125904 compound 1 Drugs 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 239000012024 dehydrating agents‎ Substances 0.000 description 2
• 125000004663 dialkyl amino group Chemical group 0.000 description 2
• SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 238000010494 dissociation reaction Methods 0.000 description 2
• 230000005593 dissociations Effects 0.000 description 2
• 238000001962 electrophoresis Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 206010015037 epilepsy Diseases 0.000 description 2
• 235000019441 ethanol Nutrition 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 2
• 230000006126 farnesylation Effects 0.000 description 2
• 230000001605 fetal effect Effects 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 239000013505 freshwater Substances 0.000 description 2
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 239000011521 glass Substances 0.000 description 2
• 239000001963 growth medium Substances 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 230000003301 hydrolyzing effect Effects 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 238000009434 installation Methods 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• 229910052742 iron Inorganic materials 0.000 description 2
• 239000012669 liquid formulation Substances 0.000 description 2
• 206010025482 malaise Diseases 0.000 description 2
• 230000003211 malignant effect Effects 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
• 235000006408 oxalic acid Nutrition 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 239000007800 oxidant agent Substances 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 201000002528 pancreatic cancer Diseases 0.000 description 2
• 238000005502 peroxidation Methods 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 230000002062 proliferating effect Effects 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• UDLWVSDXEKQRKZ-UHFFFAOYSA-N pyridin-3-yl carbonochloridate Chemical compound ClC(=O)OC1=CC=CN=C1 UDLWVSDXEKQRKZ-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
• NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
• 229910052704 radon Inorganic materials 0.000 description 2
• SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• 235000009566 rice Nutrition 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
• KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
• 229910001948 sodium oxide Inorganic materials 0.000 description 2
• 239000002689 soil Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• 238000001890 transfection Methods 0.000 description 2
• 239000003558 transferase inhibitor Substances 0.000 description 2
• 230000001131 transforming effect Effects 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 229910052721 tungsten Inorganic materials 0.000 description 2
• 239000004474 valine Substances 0.000 description 2
• 239000002699 waste material Substances 0.000 description 2
• 239000002023 wood Substances 0.000 description 2
• 229910052725 zinc Inorganic materials 0.000 description 2
• 239000011701 zinc Substances 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 1
• LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 description 1
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
• KCJYAYAPCKAHFV-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluoro-4H-pyridine Chemical compound FC1C(C(N(C=C1)F)(F)F)(F)F KCJYAYAPCKAHFV-UHFFFAOYSA-N 0.000 description 1
• AHTYGDMTPUWVOD-UHFFFAOYSA-N 1,2,2,3,3,4-hexafluoropyrazine Chemical compound FN1C(C(N(C=C1)F)(F)F)(F)F AHTYGDMTPUWVOD-UHFFFAOYSA-N 0.000 description 1
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• LZIYAIRGDHSVED-UHFFFAOYSA-N 1-(bromomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(CBr)=C1 LZIYAIRGDHSVED-UHFFFAOYSA-N 0.000 description 1
• XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• MHJPNBAEWSRKBK-UHFFFAOYSA-N 1-aminopropane-2-thiol Chemical compound CC(S)CN MHJPNBAEWSRKBK-UHFFFAOYSA-N 0.000 description 1
• DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
• NGQQUXXTDZADNX-UHFFFAOYSA-N 2,3,4,5-tetrachlorofuran Chemical compound ClC=1OC(Cl)=C(Cl)C=1Cl NGQQUXXTDZADNX-UHFFFAOYSA-N 0.000 description 1
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
• NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• VWFJDQUYCIWHTN-YFVJMOTDSA-N 2-trans,6-trans-farnesyl diphosphate Chemical class CC(C)=CCC\C(C)=C\CC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-YFVJMOTDSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
• WBXZCDIZXWDPBL-UHFFFAOYSA-N 3-methylpyridine-2-carbonitrile Chemical compound CC1=CC=CN=C1C#N WBXZCDIZXWDPBL-UHFFFAOYSA-N 0.000 description 1
• AIOUQYUFHADEHR-UHFFFAOYSA-N 3-methylpyridine-2-carboxamide Chemical compound CC1=CC=CN=C1C(N)=O AIOUQYUFHADEHR-UHFFFAOYSA-N 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
• VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 1
• ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-UHFFFAOYSA-N 0.000 description 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical group COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
• BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 1
• 244000020998 Acacia farnesiana Species 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• 241000834695 Auchenoglanis occidentalis Species 0.000 description 1
• 229910015900 BF3 Inorganic materials 0.000 description 1
• 240000000724 Berberis vulgaris Species 0.000 description 1
• 235000016068 Berberis vulgaris Nutrition 0.000 description 1
• 102100021257 Beta-secretase 1 Human genes 0.000 description 1
• 101710150192 Beta-secretase 1 Proteins 0.000 description 1
• 229930185605 Bisphenol Natural products 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 208000019838 Blood disease Diseases 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• 101100293605 Caenorhabditis elegans nas-8 gene Proteins 0.000 description 1
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
• 241001048191 Candidatus Kryptonium Species 0.000 description 1
• 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
• 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• 241001273783 Carex scoparia Species 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
• 206010052360 Colorectal adenocarcinoma Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 244000163122 Curcuma domestica Species 0.000 description 1
• 235000003392 Curcuma domestica Nutrition 0.000 description 1
• 241000006479 Cyme Species 0.000 description 1
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• 235000005903 Dioscorea Nutrition 0.000 description 1
• 244000281702 Dioscorea villosa Species 0.000 description 1
• 235000000504 Dioscorea villosa Nutrition 0.000 description 1
• 229910000976 Electrical steel Inorganic materials 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 241000588914 Enterobacter Species 0.000 description 1
• 241000283070 Equus zebra Species 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
• 241001070947 Fagus Species 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 108091006027 G proteins Proteins 0.000 description 1
• 102000030782 GTP binding Human genes 0.000 description 1
• 108091000058 GTP-Binding Proteins 0.000 description 1
• 241000735332 Gerbera Species 0.000 description 1
• SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
• DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
• 244000178870 Lavandula angustifolia Species 0.000 description 1
• 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
• 240000000599 Lentinula edodes Species 0.000 description 1
• 235000001715 Lentinula edodes Nutrition 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
• 206010024612 Lipoma Diseases 0.000 description 1
• 241000131091 Lucanus cervus Species 0.000 description 1
• 240000004658 Medicago sativa Species 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 125000000815 N-oxide group Chemical group 0.000 description 1
• KSGUUTWSWMLVHG-UHFFFAOYSA-N N.OOO Chemical compound N.OOO KSGUUTWSWMLVHG-UHFFFAOYSA-N 0.000 description 1
• 208000009905 Neurofibromatoses Diseases 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 101710190786 PI protein Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 206010033799 Paralysis Diseases 0.000 description 1
• 206010034912 Phobia Diseases 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• 229910052777 Praseodymium Inorganic materials 0.000 description 1
• 244000299790 Rheum rhabarbarum Species 0.000 description 1
• 235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
• 208000035217 Ring chromosome 1 syndrome Diseases 0.000 description 1
• 244000235659 Rubus idaeus Species 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000004350 Strabismus Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
• 241000270708 Testudinidae Species 0.000 description 1
• 102100040396 Transcobalamin-1 Human genes 0.000 description 1
• 101710124861 Transcobalamin-1 Proteins 0.000 description 1
• 229940123468 Transferase inhibitor Drugs 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
• QEPRYQNWGGLLKU-UHFFFAOYSA-I [C+4].[Cl-].[Na+].[Cl-].[Cl-].[Cl-].[Cl-] Chemical class [C+4].[Cl-].[Na+].[Cl-].[Cl-].[Cl-].[Cl-] QEPRYQNWGGLLKU-UHFFFAOYSA-I 0.000 description 1
• BUJMWNMNQVOMMW-UHFFFAOYSA-L [Cl-].[Mg+2].N1=CC=CC=C1.[Cl-] Chemical compound [Cl-].[Mg+2].N1=CC=CC=C1.[Cl-] BUJMWNMNQVOMMW-UHFFFAOYSA-L 0.000 description 1
• CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 1
• 210000001015 abdomen Anatomy 0.000 description 1
• WTHXTWHYLIZJBH-UHFFFAOYSA-N acetic acid;azane Chemical compound N.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O WTHXTWHYLIZJBH-UHFFFAOYSA-N 0.000 description 1
• ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 239000010975 amethyst Substances 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000002579 anti-swelling effect Effects 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• OVLHQUWQINALPR-UHFFFAOYSA-N azane;dichloromethane Chemical compound N.ClCCl OVLHQUWQINALPR-UHFFFAOYSA-N 0.000 description 1
• JTSVYBPWSSQBEB-UHFFFAOYSA-N azanium;hexanoate Chemical compound [NH4+].CCCCCC([O-])=O JTSVYBPWSSQBEB-UHFFFAOYSA-N 0.000 description 1
• 244000052616 bacterial pathogen Species 0.000 description 1
• UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 1
• 235000013405 beer Nutrition 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000002051 biphasic effect Effects 0.000 description 1
• 239000012455 biphasic mixture Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
• AXCGVFCNSUNRML-UHFFFAOYSA-N butane;hexane Chemical compound CCCC.CCCCCC AXCGVFCNSUNRML-UHFFFAOYSA-N 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
• KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
• HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
• 239000001110 calcium chloride Substances 0.000 description 1
• 229910001628 calcium chloride Inorganic materials 0.000 description 1
• 244000309466 calf Species 0.000 description 1
• 235000009120 camo Nutrition 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical compound [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• APOAQWCRYLYSMB-UHFFFAOYSA-N carbonic acid krypton Chemical compound C(O)(O)=O.[Kr] APOAQWCRYLYSMB-UHFFFAOYSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 231100000357 carcinogen Toxicity 0.000 description 1
• 239000003183 carcinogenic agent Substances 0.000 description 1
• 239000000969 carrier Substances 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
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000010307 cell transformation Effects 0.000 description 1
• 235000005607 chanvre indien Nutrition 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 229930002875 chlorophyll Natural products 0.000 description 1
• 235000019804 chlorophyll Nutrition 0.000 description 1
• ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
• 229940043350 citral Drugs 0.000 description 1
• 238000010367 cloning Methods 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 201000002758 colorectal adenoma Diseases 0.000 description 1
• 201000010989 colorectal carcinoma Diseases 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 239000002299 complementary DNA Substances 0.000 description 1
• 229940126543 compound 14 Drugs 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000010276 construction Methods 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• 239000013256 coordination polymer Substances 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 210000004748 cultured cell Anatomy 0.000 description 1
• 235000003373 curcuma longa Nutrition 0.000 description 1
• 238000005520 cutting process Methods 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
• OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
• 229940099500 cystamine Drugs 0.000 description 1
• UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical group NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
• 235000018417 cysteine Nutrition 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 208000002925 dental caries Diseases 0.000 description 1
• 210000003298 dental enamel Anatomy 0.000 description 1
• LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 235000004879 dioscorea Nutrition 0.000 description 1
• 150000002012 dioxanes Chemical class 0.000 description 1
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
• 239000001177 diphosphate Substances 0.000 description 1
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
• XERQTZLDFHNZIC-UHFFFAOYSA-L disodium;tellurate Chemical compound [Na+].[Na+].[O-][Te]([O-])(=O)=O XERQTZLDFHNZIC-UHFFFAOYSA-L 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 238000011978 dissolution method Methods 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• MUQJJXDUSYNGLY-UHFFFAOYSA-L erben Chemical compound O.[O-]S([O-])(=O)=O.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 MUQJJXDUSYNGLY-UHFFFAOYSA-L 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 238000003810 ethyl acetate extraction Methods 0.000 description 1
• 239000002038 ethyl acetate fraction Substances 0.000 description 1
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000009313 farming Methods 0.000 description 1
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
• 239000012091 fetal bovine serum Substances 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 238000005189 flocculation Methods 0.000 description 1
• 230000016615 flocculation Effects 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 230000003325 follicular Effects 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000005194 fractionation Methods 0.000 description 1
• 239000012737 fresh medium Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 229960003883 furosemide Drugs 0.000 description 1
• 210000000232 gallbladder Anatomy 0.000 description 1
• 238000004817 gas chromatography Methods 0.000 description 1
• 230000014509 gene expression Effects 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 238000010353 genetic engineering Methods 0.000 description 1
• WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 239000003292 glue Substances 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 150000002343 gold Chemical class 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 208000014951 hematologic disease Diseases 0.000 description 1
• 208000018706 hematopoietic system disease Diseases 0.000 description 1
• 239000011487 hemp Substances 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 238000000265 homogenisation Methods 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 239000010903 husk Substances 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• 150000002440 hydroxy compounds Chemical class 0.000 description 1
• 230000003053 immunization Effects 0.000 description 1
• 238000002649 immunization Methods 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 238000007689 inspection Methods 0.000 description 1
• 230000006525 intracellular process Effects 0.000 description 1
• VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 1
• ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 230000002045 lasting effect Effects 0.000 description 1
• 239000001102 lavandula vera Substances 0.000 description 1
• 235000018219 lavender Nutrition 0.000 description 1
• 238000002386 leaching Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 201000005249 lung adenocarcinoma Diseases 0.000 description 1
• 210000001165 lymph node Anatomy 0.000 description 1
• PCSRJTQCIJGJDE-UHFFFAOYSA-L magnesium chloromethane sulfate Chemical compound S(=O)(=O)([O-])[O-].[Mg+2].CCl PCSRJTQCIJGJDE-UHFFFAOYSA-L 0.000 description 1
• LGASAICTCFRDSN-UHFFFAOYSA-L magnesium;tellurate Chemical compound [Mg+2].[O-][Te]([O-])(=O)=O LGASAICTCFRDSN-UHFFFAOYSA-L 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 238000000691 measurement method Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• YXFSNDDMXZEMCF-UHFFFAOYSA-N methyl hydrogen sulfate;sulfuric acid Chemical compound OS(O)(=O)=O.COS(O)(=O)=O YXFSNDDMXZEMCF-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
• DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
• 238000000386 microscopy 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
• 238000003801 milling Methods 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 229910052750 molybdenum Inorganic materials 0.000 description 1
• 239000011733 molybdenum Substances 0.000 description 1
• 210000001616 monocyte Anatomy 0.000 description 1
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
• XWCCTMBMQUCLSI-UHFFFAOYSA-N n-ethyl-n-propylpropan-1-amine Chemical compound CCCN(CC)CCC XWCCTMBMQUCLSI-UHFFFAOYSA-N 0.000 description 1
• 230000017074 necrotic cell death Effects 0.000 description 1
• 230000017066 negative regulation of growth Effects 0.000 description 1
• 201000004931 neurofibromatosis Diseases 0.000 description 1
• 229960003966 nicotinamide Drugs 0.000 description 1
• 239000011570 nicotinamide Substances 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 238000006902 nitrogenation reaction Methods 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
• ZXVJACKMMUOZDX-UHFFFAOYSA-N octane;hydrate Chemical compound O.CCCCCCCC ZXVJACKMMUOZDX-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 239000005416 organic matter Substances 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 244000045947 parasite Species 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 150000002978 peroxides Chemical class 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
• 208000019899 phobic disease Diseases 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
• 239000011574 phosphorus Substances 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• 235000021110 pickles Nutrition 0.000 description 1
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 230000007096 poisonous effect Effects 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 229920001155 polypropylene Polymers 0.000 description 1
• 239000011148 porous material Substances 0.000 description 1
• 230000034918 positive regulation of cell growth Effects 0.000 description 1
• 230000031055 positive regulation of mitosis Effects 0.000 description 1
• 150000003109 potassium Chemical class 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 239000001103 potassium chloride Substances 0.000 description 1
• 235000011164 potassium chloride Nutrition 0.000 description 1
• CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
• 229910001950 potassium oxide Inorganic materials 0.000 description 1
• KOKMIVTXKODVQK-UHFFFAOYSA-M potassium;benzenecarboperoxoate Chemical compound [K+].[O-]OC(=O)C1=CC=CC=C1 KOKMIVTXKODVQK-UHFFFAOYSA-M 0.000 description 1
• PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 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 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 235000004252 protein component Nutrition 0.000 description 1
• 230000009145 protein modification Effects 0.000 description 1
• BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical class C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 239000011677 pyridoxine Substances 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 239000008911 qingzhi Substances 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 238000007347 radical substitution reaction Methods 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008439 repair process Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 229910052702 rhenium Inorganic materials 0.000 description 1
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
• 102220005136 rs33918778 Human genes 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 210000003296 saliva Anatomy 0.000 description 1
• 239000012723 sample buffer Substances 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 150000003378 silver Chemical class 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 201000008261 skin carcinoma Diseases 0.000 description 1
• 238000003307 slaughter Methods 0.000 description 1
• 239000010802 sludge Substances 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000004317 sodium nitrate Substances 0.000 description 1
• 235000010344 sodium nitrate Nutrition 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000010025 steaming Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 210000004243 sweat Anatomy 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000003760 tallow Substances 0.000 description 1
• ZTBJFXYWWZPTFM-UHFFFAOYSA-N tellanylidenemagnesium Chemical compound [Te]=[Mg] ZTBJFXYWWZPTFM-UHFFFAOYSA-N 0.000 description 1
• MVGWWCXDTHXKTR-UHFFFAOYSA-J tetralithium;phosphonato phosphate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]P([O-])(=O)OP([O-])([O-])=O MVGWWCXDTHXKTR-UHFFFAOYSA-J 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 231100001274 therapeutic index Toxicity 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
• 230000002992 thymic effect Effects 0.000 description 1
• 210000001541 thymus gland Anatomy 0.000 description 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 230000005760 tumorsuppression Effects 0.000 description 1
• WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
• 239000010937 tungsten Substances 0.000 description 1
• 235000013976 turmeric Nutrition 0.000 description 1
• 210000003954 umbilical cord Anatomy 0.000 description 1
• 241001430294 unidentified retrovirus Species 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• 229940011671 vitamin b6 Drugs 0.000 description 1
• 238000010792 warming Methods 0.000 description 1