JP5577256B2 - 抗腫瘍化合物 - Google Patents

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Publication number

JP5577256B2

JP5577256B2 JP2010537432A JP2010537432A JP5577256B2 JP 5577256 B2 JP5577256 B2 JP 5577256B2 JP 2010537432 A JP2010537432 A JP 2010537432A JP 2010537432 A JP2010537432 A JP 2010537432A JP 5577256 B2 JP5577256 B2 JP 5577256B2

Authority

JP

Japan

Prior art keywords

substituted

unsubstituted

group

carbamate

methyl

Prior art date

2007-12-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 92
• 230000000259 anti-tumor effect Effects 0.000 title description 7
• 125000006239 protecting group Chemical group 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000001118 alkylidene group Chemical group 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 2
• 239000000463 material Substances 0.000 claims 4
• 239000003795 chemical substances by application Substances 0.000 claims 1
• -1 2-hydroxyquinolyl group Chemical group 0.000 description 170
• 108090000765 processed proteins & peptides Proteins 0.000 description 30
• 239000011347 resin Substances 0.000 description 28
• 229920005989 resin Polymers 0.000 description 28
• 239000000203 mixture Substances 0.000 description 26
• 238000000034 method Methods 0.000 description 19
• 239000000243 solution Substances 0.000 description 18
• 210000004027 cell Anatomy 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• 230000015572 biosynthetic process Effects 0.000 description 14
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
• 125000003277 amino group Chemical group 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 229940125782 compound 2 Drugs 0.000 description 9
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 239000003643 water by type Substances 0.000 description 8
• WCHAVJJXSIQEMZ-DOZAELEDSA-N 3-hydroxy-n-[(1r,7r,11r,14s,20r,24r)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-28,29-dithia-2,5,9,12,15,18,22,25-octazabicyclo[12.12.3]nonacosan-20-yl]quinoline-2-carboxam Chemical compound O=C([C@@H]1SSC[C@H](N(C(=O)CNC2=O)C)C(=O)N(C)[C@H](C(NC[C@H](C(=O)NCC(=O)N1C)NC(=O)C=1C(=CC3=CC=CC=C3N=1)O)=O)CSC)N(C)[C@@H](CSC)C(=O)NC[C@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O WCHAVJJXSIQEMZ-DOZAELEDSA-N 0.000 description 7
• UPGGKUQISSWRJJ-ZRBWWFCKSA-N 3-hydroxy-n-[(1r,7s,11s,14r,20s,24s)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-20-yl]quinoline-2-carb Chemical compound O=C([C@@H]1CSSC[C@H](N(C(=O)CNC2=O)C)C(=O)N(C)[C@H](C(SC[C@H](C(=O)NCC(=O)N1C)NC(=O)C=1C(=CC3=CC=CC=C3N=1)O)=O)CSC)N(C)[C@@H](CSC)C(=O)SC[C@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O UPGGKUQISSWRJJ-ZRBWWFCKSA-N 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• 238000005859 coupling reaction Methods 0.000 description 7
• 239000000539 dimer Substances 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
• 108010070024 azathiocoraline Proteins 0.000 description 6
• 244000309464 bull Species 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 229910052736 halogen Inorganic materials 0.000 description 6
• 150000002367 halogens Chemical class 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 5
• IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000002246 antineoplastic agent Substances 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 238000003776 cleavage reaction Methods 0.000 description 4
• 230000001472 cytotoxic effect Effects 0.000 description 4
• 230000003013 cytotoxicity Effects 0.000 description 4
• 231100000135 cytotoxicity Toxicity 0.000 description 4
• 238000010511 deprotection reaction Methods 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
• 238000011160 research Methods 0.000 description 4
• 238000007363 ring formation reaction Methods 0.000 description 4
• 230000007017 scission Effects 0.000 description 4
• 239000012453 solvate Substances 0.000 description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• 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 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 238000002835 absorbance Methods 0.000 description 3
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 235000001014 amino acid Nutrition 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 3
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
• 235000019439 ethyl acetate Nutrition 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 150000004677 hydrates Chemical class 0.000 description 3
• 125000002883 imidazolyl group Chemical group 0.000 description 3
• 125000001041 indolyl group Chemical group 0.000 description 3
• 125000005956 isoquinolyl group Chemical group 0.000 description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 3
• CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 3
• GULVULFEAVZHHC-SZZROTLHSA-N n-[(1s,4s,7r,11s,14s,17s,20r,24s)-2,4,12,15,17,25-hexamethyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@H]1CSSC[C@@H](N(C(=O)[C@H](C)NC2=O)C)C(=O)N(C)[C@H](C(OC[C@H](C(=O)N[C@@H](C)C(=O)N1C)NC(=O)C=1N=C3C=CC=CC3=NC=1)=O)C(C)C)N(C)[C@@H](C(C)C)C(=O)OC[C@H]2NC(=O)C1=CN=C(C=CC=C2)C2=N1 GULVULFEAVZHHC-SZZROTLHSA-N 0.000 description 3
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 3
• 239000012044 organic layer Substances 0.000 description 3
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
• 229940049953 phenylacetate Drugs 0.000 description 3
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
• AWOKSNNHYRGYIA-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl carbamate Chemical compound COC1=CC(COC(N)=O)=C([N+]([O-])=O)C=C1OC AWOKSNNHYRGYIA-UHFFFAOYSA-N 0.000 description 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
• UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 2
• 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
• QLOZXPNJEDVFIH-ZRTHHSRSSA-N 3-hydroxy-n-[(1r,7s,14r,20s)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-dimethylidene-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-20-yl]quinoline-2-carboxamide Chemical compound CN([C@H]1CSSC[C@@H](C(N(C)C(=C)C(=O)SC2)=O)N(C(CNC(=O)[C@H](NC(=O)C=3C(=CC4=CC=CC=C4N=3)O)CSC(=O)C(=C)N(C)C1=O)=O)C)C(=O)CNC(=O)[C@@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O QLOZXPNJEDVFIH-ZRTHHSRSSA-N 0.000 description 2
• WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 description 2
• ACMIJDVJWLMBCX-PXAZEXFGSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-6-fluoro-n-methyl-2-(2-methylpyrimidin-5-yl)oxy-9h-pyrimido[4,5-b]indol-8-amine Chemical compound CNC1=CC(F)=CC(C2=C(N3C[C@@H]4NCC[C@@H]4C3)N=3)=C1NC2=NC=3OC1=CN=C(C)N=C1 ACMIJDVJWLMBCX-PXAZEXFGSA-N 0.000 description 2
• JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• 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 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
• 229910014299 N-Si Inorganic materials 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
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 239000004698 Polyethylene Substances 0.000 description 2
• 239000004743 Polypropylene Substances 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
• GULVULFEAVZHHC-UHFFFAOYSA-N Triostin-A Natural products CN1C(=O)C(C)NC(=O)C(NC(=O)C=2N=C3C=CC=CC3=NC=2)COC(=O)C(C(C)C)N(C)C(=O)C(N(C(=O)C(C)NC2=O)C)CSSCC1C(=O)N(C)C(C(C)C)C(=O)OCC2NC(=O)C1=CN=C(C=CC=C2)C2=N1 GULVULFEAVZHHC-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 239000004305 biphenyl Substances 0.000 description 2
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• HAUXSVQKDKQHTF-UHFFFAOYSA-N carbon monoxide;chromium Chemical compound [Cr].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] HAUXSVQKDKQHTF-UHFFFAOYSA-N 0.000 description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
• 230000004663 cell proliferation Effects 0.000 description 2
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