JP2004513063A5

JP2004513063A5 -

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Publication number: JP2004513063A5
Authority: JP; Japan
Prior art keywords: phenyl; carbonyl; ethenyl; sulfide; nitro
Prior art date: 2000-04-03
Legal status : Ceased

Application number

JP2000609392A

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English (en)

Japanese (ja)

Other versions

JP2004513063A (ja

Filing date

2000-04-03

Publication date

2006-05-11

2000-03-31 Priority claimed from US09/541,795 external-priority patent/US6878700B1/en

2000-04-03 Application filed filed Critical

2000-04-03 Priority claimed from PCT/US2000/008895 external-priority patent/WO2000059880A1/en

2004-04-30 Publication of JP2004513063A publication Critical patent/JP2004513063A/ja

2006-05-11 Publication of JP2004513063A5 publication Critical patent/JP2004513063A5/ja

Status Ceased legal-status Critical Current

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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 160
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 140
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 136
-1 2- (hydroxymethyl) phenyl Chemical group 0.000 description 128
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 110
125000005322 morpholin-1-yl group Chemical group 0.000 description 42
150000001875 compounds Chemical class 0.000 description 29
125000000623 heterocyclic group Chemical group 0.000 description 18
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 17
125000000217 alkyl group Chemical group 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
239000001257 hydrogen Substances 0.000 description 15
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 11
GZTFUVZVLYUPRG-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(OCCO2)C2=C1 GZTFUVZVLYUPRG-IZZDOVSWSA-N 0.000 description 10
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 10
125000004415 heterocyclylalkyl group Chemical group 0.000 description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
125000004181 carboxyalkyl group Chemical group 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
125000002768 hydroxyalkyl group Chemical group 0.000 description 8
238000000034 method Methods 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
125000004103 aminoalkyl group Chemical group 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
125000001188 haloalkyl group Chemical group 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000004183 alkoxy alkyl group Chemical group 0.000 description 4
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 4
125000003831 tetrazolyl group Chemical group 0.000 description 4
VZZCQRNZLSYOOW-NXZHAISVSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[4-[4-[(e)-3-(4-acetylpiperazin-1-yl)-3-oxoprop-1-enyl]-2-nitrophenyl]sulfanyl-3-nitrophenyl]prop-2-en-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CCN(C(C)=O)CC1 VZZCQRNZLSYOOW-NXZHAISVSA-N 0.000 description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
UOFAKKLUWZNFLJ-UHFFFAOYSA-N FC(C1=C(C=CC(=C1)C=CC(=O)N1CC(CC1)C(=O)O)SC1=CC2=C(OCCO2)C=C1)(F)F Chemical compound FC(C1=C(C=CC(=C1)C=CC(=O)N1CC(CC1)C(=O)O)SC1=CC2=C(OCCO2)C=C1)(F)F UOFAKKLUWZNFLJ-UHFFFAOYSA-N 0.000 description 3
241000257303 Hymenoptera Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
150000003857 carboxamides Chemical class 0.000 description 3
KZPLGJADSZYMOB-WYMLVPIESA-N ethyl 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C KZPLGJADSZYMOB-WYMLVPIESA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
GYELUVCNTNLZSS-XVNBXDOJSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-en-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 GYELUVCNTNLZSS-XVNBXDOJSA-N 0.000 description 2
UIUXITYGSWCSTE-PKNBQFBNSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[2,3-dichloro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-en-1-one Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CCN(C(C)=O)CC1 UIUXITYGSWCSTE-PKNBQFBNSA-N 0.000 description 2
FVEAFWBHBUVJQZ-XVNBXDOJSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[3-chloro-4-[[2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]phenyl]prop-2-en-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=C(OC(CO)CO2)C2=C1 FVEAFWBHBUVJQZ-XVNBXDOJSA-N 0.000 description 2
BDAORFGUEOEJOL-SOFGYWHQSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[4-(3-morpholin-4-ylphenyl)sulfanyl-3-nitrophenyl]prop-2-en-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC(N2CCOCC2)=C1 BDAORFGUEOEJOL-SOFGYWHQSA-N 0.000 description 2
SPCYRQITFPNZIC-WEVVVXLNSA-N (e)-1-(4-acetylpiperazin-1-yl)-3-[4-(4-bromo-2-ethylphenyl)sulfanyl-3-nitrophenyl]prop-2-en-1-one Chemical compound CCC1=CC(Br)=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CCN(C(C)=O)CC1 SPCYRQITFPNZIC-WEVVVXLNSA-N 0.000 description 2
TYSNSNCFBVFJHM-VQHVLOKHSA-N (e)-1-[4-(2-hydroxyethyl)piperazin-1-yl]-3-[4-(2-methoxyphenyl)sulfanyl-2,3-bis(trifluoromethyl)phenyl]prop-2-en-1-one Chemical compound COC1=CC=CC=C1SC(C(=C1C(F)(F)F)C(F)(F)F)=CC=C1\C=C\C(=O)N1CCN(CCO)CC1 TYSNSNCFBVFJHM-VQHVLOKHSA-N 0.000 description 2
FMUSKQFEAQDFGB-WEVVVXLNSA-N (e)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]-n-[3-(2-oxopyrrolidin-1-yl)propyl]prop-2-enamide Chemical compound C=1C=C(SC=2C=C3OCCOC3=CC=2)C(Cl)=C(Cl)C=1\C=C\C(=O)NCCCN1CCCC1=O FMUSKQFEAQDFGB-WEVVVXLNSA-N 0.000 description 2
VSQRFWRJCYAAIO-FCXRPNKRSA-N (e)-3-[2,3-dichloro-4-[2,3-dichloro-4-[(e)-3-morpholin-4-yl-3-oxoprop-1-enyl]phenyl]sulfanylphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound C=1C=C(SC=2C(=C(Cl)C(\C=C\C(=O)N3CCOCC3)=CC=2)Cl)C(Cl)=C(Cl)C=1\C=C\C(=O)N1CCOCC1 VSQRFWRJCYAAIO-FCXRPNKRSA-N 0.000 description 2
DPGFCSWVVLMDEL-UTLPMFLDSA-N (e)-3-[3-nitro-4-[2-nitro-4-[(e)-3-oxo-3-[3-(2-oxopyrrolidin-1-yl)propylamino]prop-1-enyl]phenyl]sulfanylphenyl]-n-[3-(2-oxopyrrolidin-1-yl)propyl]prop-2-enamide Chemical compound C=1C=C(SC=2C(=CC(\C=C\C(=O)NCCCN3C(CCC3)=O)=CC=2)[N+]([O-])=O)C([N+](=O)[O-])=CC=1\C=C\C(=O)NCCCN1CCCC1=O DPGFCSWVVLMDEL-UTLPMFLDSA-N 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
RMWVZTTXBRENMI-XBXARRHUSA-N 1-[(e)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 RMWVZTTXBRENMI-XBXARRHUSA-N 0.000 description 2
HSJWUDLCVCZMAZ-QHHAFSJGSA-N 1-[(e)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 HSJWUDLCVCZMAZ-QHHAFSJGSA-N 0.000 description 2
QPWDZBBZIVDASP-VQHVLOKHSA-N 1-[(e)-3-[2,3-dichloro-4-(2-methoxyphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carboxylic acid Chemical compound COC1=CC=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CCC(C(O)=O)CC1 QPWDZBBZIVDASP-VQHVLOKHSA-N 0.000 description 2
NNUXZLHZSXDGJB-ZRDIBKRKSA-N 1-[(e)-3-[2,3-dichloro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CC(C(O)=O)CCC1 NNUXZLHZSXDGJB-ZRDIBKRKSA-N 0.000 description 2
SYGPJZDISKKEIV-CSKARUKUSA-N 1-[(e)-3-[2,3-dichloro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carboxylic acid Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CCC(C(O)=O)CC1 SYGPJZDISKKEIV-CSKARUKUSA-N 0.000 description 2
VDKSZPCTZWBYMR-WEVVVXLNSA-N 1-[(e)-3-[3-chloro-4-(1-methylindol-5-yl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound C=1C=C2N(C)C=CC2=CC=1SC(C(=C1)Cl)=CC=C1\C=C\C(=O)N1CCCC(C(O)=O)C1 VDKSZPCTZWBYMR-WEVVVXLNSA-N 0.000 description 2
QTPXZSIGNYNOQR-ZRDIBKRKSA-N 1-[(e)-3-[3-chloro-4-(2-ethoxyphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound CCOC1=CC=CC=C1SC(C(=C1)Cl)=CC=C1\C=C\C(=O)N1CC(C(O)=O)CCC1 QTPXZSIGNYNOQR-ZRDIBKRKSA-N 0.000 description 2
MRWGXKWDMVKCMX-ZRDIBKRKSA-N 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C(O)=O)CCC1 MRWGXKWDMVKCMX-ZRDIBKRKSA-N 0.000 description 2
GRNIONNIYDIOAU-PKNBQFBNSA-N 1-[(e)-3-[4-(2-ethoxyphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]-4-methoxycarbonylpiperazine-2-carboxylic acid Chemical compound CCOC1=CC=CC=C1SC(C(=C1)C(F)(F)F)=CC=C1\C=C\C(=O)N1C(C(O)=O)CN(C(=O)OC)CC1 GRNIONNIYDIOAU-PKNBQFBNSA-N 0.000 description 2
VKPOQONHIOHSHY-FCXRPNKRSA-N 1-[(e)-3-[4-[4-[(e)-3-(4-carboxypiperidin-1-yl)-3-oxoprop-1-enyl]-2,3-dichlorophenyl]sulfanyl-2,3-dichlorophenyl]prop-2-enoyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CCC(C(O)=O)CC1 VKPOQONHIOHSHY-FCXRPNKRSA-N 0.000 description 2
WJTLPLQINKCYFS-ACCUITESSA-N 1-acetyl-n,n-dimethyl-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxamide Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C(=O)N(C)C)N(C(C)=O)CC1 WJTLPLQINKCYFS-ACCUITESSA-N 0.000 description 2
JOGGIPBFAFXTJX-VQHVLOKHSA-N 2-[4-[(e)-3-(4-acetylpiperazin-1-yl)-3-oxoprop-1-enyl]-2-nitrophenyl]sulfanylbenzaldehyde Chemical compound C1CN(C(=O)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C=O JOGGIPBFAFXTJX-VQHVLOKHSA-N 0.000 description 2
OLTYCMVTDHZBKO-VQHVLOKHSA-N 2-[4-[(e)-3-[4-(2-methoxyphenyl)sulfanyl-2,3-bis(trifluoromethyl)phenyl]prop-2-enoyl]piperazin-1-yl]acetic acid Chemical compound COC1=CC=CC=C1SC(C(=C1C(F)(F)F)C(F)(F)F)=CC=C1\C=C\C(=O)N1CCN(CC(O)=O)CC1 OLTYCMVTDHZBKO-VQHVLOKHSA-N 0.000 description 2
NKCCQRQDKPMDNH-VQHVLOKHSA-N 2-[[1-[(e)-3-[2,3-dichloro-4-(2-methoxyphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1SC(C(=C1Cl)Cl)=CC=C1\C=C\C(=O)N1CCC(C(=O)NCC(O)=O)CC1 NKCCQRQDKPMDNH-VQHVLOKHSA-N 0.000 description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
QKEPHKREXDLNBL-UHFFFAOYSA-N C(C)(C)C1=C(C=CC=C1)SC1=C(C=C(C=C1)C=CC(=O)NCCCN1C(CCC1)=O)[N+](=O)[O-] Chemical compound C(C)(C)C1=C(C=CC=C1)SC1=C(C=C(C=C1)C=CC(=O)NCCCN1C(CCC1)=O)[N+](=O)[O-] QKEPHKREXDLNBL-UHFFFAOYSA-N 0.000 description 2
DYWTVOWFPATBQE-UHFFFAOYSA-N FC(C1=C(C=CC(=C1)C=CC(=O)N1C(CN(CC1)C(=O)OC)C(=O)OC)SC1=CC2=C(OCCO2)C=C1)(F)F Chemical compound FC(C1=C(C=CC(=C1)C=CC(=O)N1C(CN(CC1)C(=O)OC)C(=O)OC)SC1=CC2=C(OCCO2)C=C1)(F)F DYWTVOWFPATBQE-UHFFFAOYSA-N 0.000 description 2
GPKRILNKTWUABW-UTLPMFLDSA-N FC(C1=C(C=CC(=C1)\C=C\C(=O)NCCCN1C(CCC1)=O)SC1=C(C=C(C=C1)\C=C\C(=O)NCCCN1C(CCC1)=O)C(F)(F)F)(F)F Chemical compound FC(C1=C(C=CC(=C1)\C=C\C(=O)NCCCN1C(CCC1)=O)SC1=C(C=C(C=C1)\C=C\C(=O)NCCCN1C(CCC1)=O)C(F)(F)F)(F)F GPKRILNKTWUABW-UTLPMFLDSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000005041 acyloxyalkyl group Chemical group 0.000 description 2
125000005236 alkanoylamino group Chemical group 0.000 description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 2
125000005111 carboxyalkoxy group Chemical group 0.000 description 2
235000013985 cinnamic acid Nutrition 0.000 description 2
229930016911 cinnamic acid Natural products 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
POKKQEUASYDBBQ-WGLAMXGCSA-N ethyl (3R)-1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound O1CCOC2=C1C=CC(=C2)SC1=C(C=C(C=C1)\C=C\C(=O)N1C[C@@H](CCC1)C(=O)OCC)C(F)(F)F POKKQEUASYDBBQ-WGLAMXGCSA-N 0.000 description 2
GESBMZJMJNAQHR-UHFFFAOYSA-N ethyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)OCC)C(F)(F)F GESBMZJMJNAQHR-UHFFFAOYSA-N 0.000 description 2
MSSOOCRAPXGFEV-UXBLZVDNSA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 MSSOOCRAPXGFEV-UXBLZVDNSA-N 0.000 description 2
RKJAEFXJQANYMD-XBXARRHUSA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 RKJAEFXJQANYMD-XBXARRHUSA-N 0.000 description 2
BMDQQSUVOZSERD-WYMLVPIESA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=CC=C1C(C)C BMDQQSUVOZSERD-WYMLVPIESA-N 0.000 description 2
QRRQINIHJFFKAH-PKNBQFBNSA-N ethyl 1-[(e)-3-[3-chloro-4-(2-methoxyphenyl)sulfanyl-2-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C(C(=C1Cl)C(F)(F)F)=CC=C1SC1=CC=CC=C1OC QRRQINIHJFFKAH-PKNBQFBNSA-N 0.000 description 2
TWECJSGBASPKJL-VQHVLOKHSA-N ethyl 1-[(e)-3-[4-(3-bromophenyl)sulfanyl-3-nitrophenyl]prop-2-enoyl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC(Br)=C1 TWECJSGBASPKJL-VQHVLOKHSA-N 0.000 description 2
125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
230000028993 immune response Effects 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
OZGXUKLUMFUBCN-UHFFFAOYSA-N methyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-2-carboxylate Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2C(CNCC2)C(=O)OC)C(F)(F)F OZGXUKLUMFUBCN-UHFFFAOYSA-N 0.000 description 2
IBVWEADVZCIAMD-PKNBQFBNSA-N methyl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C IBVWEADVZCIAMD-PKNBQFBNSA-N 0.000 description 2
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
125000003431 oxalo group Chemical group 0.000 description 2
LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical group C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
125000004001 thioalkyl group Chemical group 0.000 description 2
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POVGRZDJKVCZMV-ZRDIBKRKSA-N (e)-1-(4-acetyl-3-methylpiperazin-1-yl)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-en-1-one Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C)N(C(C)=O)CC1 POVGRZDJKVCZMV-ZRDIBKRKSA-N 0.000 description 1
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DOXUHDLFAHFISO-PKNBQFBNSA-N 1-[3-[4-[(e)-3-[bis(2-ethoxyethyl)amino]-3-oxoprop-1-enyl]-2,3-bis(trifluoromethyl)phenyl]sulfanylphenyl]piperidine-4-carboxylic acid Chemical compound FC(F)(F)C1=C(C(F)(F)F)C(/C=C/C(=O)N(CCOCC)CCOCC)=CC=C1SC1=CC=CC(N2CCC(CC2)C(O)=O)=C1 DOXUHDLFAHFISO-PKNBQFBNSA-N 0.000 description 1
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PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
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POKKQEUASYDBBQ-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CC(CCC2)C(=O)OCC)C(F)(F)F Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CC(CCC2)C(=O)OCC)C(F)(F)F POKKQEUASYDBBQ-UHFFFAOYSA-N 0.000 description 1
XVNFOTUJUGMVJY-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)NS(=O)(=O)CC)C(F)(F)F Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)NS(=O)(=O)CC)C(F)(F)F XVNFOTUJUGMVJY-UHFFFAOYSA-N 0.000 description 1
HQPMLFPRUBYDMR-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)O)[N+](=O)[O-] Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)O)[N+](=O)[O-] HQPMLFPRUBYDMR-UHFFFAOYSA-N 0.000 description 1
KLFIJMSSCSPARV-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)OCC)[N+](=O)[O-] Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)C(=O)OCC)[N+](=O)[O-] KLFIJMSSCSPARV-UHFFFAOYSA-N 0.000 description 1
VGCSEVBMXRIMJD-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)N2CCCC2)C(F)(F)F Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2CCC(CC2)N2CCCC2)C(F)(F)F VGCSEVBMXRIMJD-UHFFFAOYSA-N 0.000 description 1
SYUKZXOUXJVLJD-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)NCCCN2C(CCC2)=O)C(F)(F)F Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)NCCCN2C(CCC2)=O)C(F)(F)F SYUKZXOUXJVLJD-UHFFFAOYSA-N 0.000 description 1
HDVLJCMIKFUCRS-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)NCCCN2C(CCC2)=O)[N+](=O)[O-] Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)NCCCN2C(CCC2)=O)[N+](=O)[O-] HDVLJCMIKFUCRS-UHFFFAOYSA-N 0.000 description 1
JWFUOBPMWZQUOP-SOFGYWHQSA-N O=C(/C=C/C(C=C1Cl)=CC=C1SC1=CC=CC=C1Br)[S+]1CCNCC1 Chemical compound O=C(/C=C/C(C=C1Cl)=CC=C1SC1=CC=CC=C1Br)[S+]1CCNCC1 JWFUOBPMWZQUOP-SOFGYWHQSA-N 0.000 description 1
WLTMNESBCNHGJQ-FCXRPNKRSA-N OC(CCN(C1)C(/C=C/C(C=CC(SC(C=CC(/C=C/C(N(CCC2O)CC2C(O)=O)=O)=C2Cl)=C2Cl)=C2Cl)=C2Cl)=O)C1C(O)=O Chemical compound OC(CCN(C1)C(/C=C/C(C=CC(SC(C=CC(/C=C/C(N(CCC2O)CC2C(O)=O)=O)=C2Cl)=C2Cl)=C2Cl)=C2Cl)=O)C1C(O)=O WLTMNESBCNHGJQ-FCXRPNKRSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
244000097202 Rathbunia alamosensis Species 0.000 description 1
235000009776 Rathbunia alamosensis Nutrition 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
OURRXQUGYQRVML-AREMUKBSSA-N [4-[(2s)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate Chemical compound CC1=CC(C)=CC=C1C(=O)OCC1=CC=C([C@@H](CN)C(=O)NC=2C=C3C=CN=CC3=CC=2)C=C1 OURRXQUGYQRVML-AREMUKBSSA-N 0.000 description 1
RMTMUFPIMGSIBL-PKNBQFBNSA-N [N+](=O)([O-])C1=C(C=CC(=C1)\C=C\C(=O)N1CC(N(CC1)C)C(=O)O)SC1=C(C=CC=C1)C(C)C Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)\C=C\C(=O)N1CC(N(CC1)C)C(=O)O)SC1=C(C=CC=C1)C(C)C RMTMUFPIMGSIBL-PKNBQFBNSA-N 0.000 description 1
JUQFXRKMADEGDM-WEVVVXLNSA-N [N+](=O)([O-])C1=C(C=CC(=C1)\C=C\C(=O)N1CCC(CC1)C(=O)OC(C)(C)C)SC1=CC2=C(OCCO2)C=C1 Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)\C=C\C(=O)N1CCC(CC1)C(=O)OC(C)(C)C)SC1=CC2=C(OCCO2)C=C1 JUQFXRKMADEGDM-WEVVVXLNSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
150000001504 aryl thiols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
GHAUVCFLOKOZPL-XVNBXDOJSA-N c1cc2n(C)ccc2cc1Sc(c(c1Cl)Cl)ccc1\C=C\C(=O)S1(=O)CCNCC1 Chemical compound c1cc2n(C)ccc2cc1Sc(c(c1Cl)Cl)ccc1\C=C\C(=O)S1(=O)CCNCC1 GHAUVCFLOKOZPL-XVNBXDOJSA-N 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
ZCDZVXRKMRBYJE-XBXARRHUSA-N dimethyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-3,4-dicarboxylate Chemical compound FC(C1=C(C=CC(=C1)\C=C\C(=O)N1CC(C(CC1)C(=O)OC)C(=O)OC)SC1=CC2=C(OCCO2)C=C1)(F)F ZCDZVXRKMRBYJE-XBXARRHUSA-N 0.000 description 1
UKSQINXBVOHLJK-ZRDIBKRKSA-N dimethyl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1,3-dicarboxylate Chemical compound COC(=O)C1CN(C(=O)OC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C UKSQINXBVOHLJK-ZRDIBKRKSA-N 0.000 description 1
IVMBDZSEXRDWBH-ZRDIBKRKSA-N dimethyl 4-[(e)-3-[4-(2-ethoxyphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1,3-dicarboxylate Chemical compound CCOC1=CC=CC=C1SC(C(=C1)C(F)(F)F)=CC=C1\C=C\C(=O)N1C(C(=O)OC)CN(C(=O)OC)CC1 IVMBDZSEXRDWBH-ZRDIBKRKSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
NDGHCNUQNQLQJF-UHFFFAOYSA-N ethyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-2-carboxylate Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2C(CCCC2)C(=O)OCC)C(F)(F)F NDGHCNUQNQLQJF-UHFFFAOYSA-N 0.000 description 1
SNLTUXSAXIJIKA-UHFFFAOYSA-N ethyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-nitrophenyl]prop-2-enoyl]piperidine-2-carboxylate Chemical compound O1CCOC2=C1C=CC(=C2)SC2=C(C=C(C=C2)C=CC(=O)N2C(CCCC2)C(=O)OCC)[N+](=O)[O-] SNLTUXSAXIJIKA-UHFFFAOYSA-N 0.000 description 1
JKFJHXHGHSILBP-YRNVUSSQSA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(1-methylindol-5-yl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(N(C)C=C2)C2=C1 JKFJHXHGHSILBP-YRNVUSSQSA-N 0.000 description 1
YZVPQALMTULWMF-WEVVVXLNSA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(1-methylindol-5-yl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=C(N(C)C=C2)C2=C1 YZVPQALMTULWMF-WEVVVXLNSA-N 0.000 description 1
UNFBPMWPUUAFSD-ZRDIBKRKSA-N ethyl 1-[(e)-3-[2,3-dichloro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C(C(=C1Cl)Cl)=CC=C1SC1=CC=CC=C1C(C)C UNFBPMWPUUAFSD-ZRDIBKRKSA-N 0.000 description 1
VNACACXLLIYMSR-WYMLVPIESA-N ethyl 1-[(e)-3-[2,3-difluoro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C(=C1F)F)=CC=C1SC1=CC=CC=C1C(C)C VNACACXLLIYMSR-WYMLVPIESA-N 0.000 description 1
VEACJBAGFAXGAI-YRNVUSSQSA-N ethyl 1-[(e)-3-[3-chloro-4-(1-methylindol-5-yl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=C(N(C)C=C2)C2=C1 VEACJBAGFAXGAI-YRNVUSSQSA-N 0.000 description 1
WESZPOORJCWFLT-YRNVUSSQSA-N ethyl 1-[(e)-3-[3-chloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 WESZPOORJCWFLT-YRNVUSSQSA-N 0.000 description 1
VAZREKHCXCOORH-UXBLZVDNSA-N ethyl 1-[(e)-3-[3-chloro-4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)phenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=C(OCCO2)C2=C1 VAZREKHCXCOORH-UXBLZVDNSA-N 0.000 description 1
JTNDDCWAQRMPPU-FYWRMAATSA-N ethyl 1-[(e)-3-[3-chloro-4-(2-ethoxyphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=CC=C1OCC JTNDDCWAQRMPPU-FYWRMAATSA-N 0.000 description 1
IOTZKZSHZWZBIE-WYMLVPIESA-N ethyl 1-[(e)-3-[3-chloro-4-(2-ethoxyphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=CC=C1OCC IOTZKZSHZWZBIE-WYMLVPIESA-N 0.000 description 1
BVSQUYBUSCQLPI-FYWRMAATSA-N ethyl 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C BVSQUYBUSCQLPI-FYWRMAATSA-N 0.000 description 1
SYRISSMRHXYAQE-ZRDIBKRKSA-N ethyl 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C SYRISSMRHXYAQE-ZRDIBKRKSA-N 0.000 description 1
AKZRTOVDAQHFPP-ZRDIBKRKSA-N ethyl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxylate Chemical compound C1CNC(C(=O)OCC)CN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C AKZRTOVDAQHFPP-ZRDIBKRKSA-N 0.000 description 1
HFSDHWVQACPHEF-ZRDIBKRKSA-N ethyl 4-[(e)-3-[4-(2-ethoxyphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1OCC HFSDHWVQACPHEF-ZRDIBKRKSA-N 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229930005346 hydroxycinnamic acid Natural products 0.000 description 1
235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
XEZAYSDVLNRFHW-XVNBXDOJSA-N methyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-4-carboxylate Chemical compound FC(C1=C(C=CC(=C1)\C=C\C(=O)N1CCC(CC1)C(=O)OC)SC1=CC2=C(OCCO2)C=C1)(F)F XEZAYSDVLNRFHW-XVNBXDOJSA-N 0.000 description 1
XGWJRJMLOBZCNY-PKNBQFBNSA-N methyl 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C XGWJRJMLOBZCNY-PKNBQFBNSA-N 0.000 description 1
YDZZFBICTXOYAW-PKNBQFBNSA-N methyl 1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxylate Chemical compound COC(=O)C1CNCCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C YDZZFBICTXOYAW-PKNBQFBNSA-N 0.000 description 1
TWGCEDNSNJFXPX-ZRDIBKRKSA-N methyl 1-[(e)-3-[4-(2-ethoxyphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]-4-methylpiperazine-2-carboxylate Chemical compound CCOC1=CC=CC=C1SC(C(=C1)C(F)(F)F)=CC=C1\C=C\C(=O)N1C(C(=O)OC)CN(C)CC1 TWGCEDNSNJFXPX-ZRDIBKRKSA-N 0.000 description 1
MUOAKIRTVMTVMZ-ZRDIBKRKSA-N methyl 1-acetyl-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxylate Chemical compound C1CN(C(C)=O)C(C(=O)OC)CN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C MUOAKIRTVMTVMZ-ZRDIBKRKSA-N 0.000 description 1
AIZYORFHDSOHSM-ACCUITESSA-N methyl 2-(dimethylcarbamoyl)-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1C(C(=O)N(C)C)N(C(=O)OC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C AIZYORFHDSOHSM-ACCUITESSA-N 0.000 description 1
DEABNERZBCCLOD-PKNBQFBNSA-N methyl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxylate Chemical compound C1CNC(C(=O)OC)CN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C DEABNERZBCCLOD-PKNBQFBNSA-N 0.000 description 1
IICNSSHNYMUFAM-PKNBQFBNSA-N methyl 4-hydroxy-1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperidine-3-carboxylate Chemical compound C1CC(O)C(C(=O)OC)CN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C IICNSSHNYMUFAM-PKNBQFBNSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
QGBKOCWAAJUPEH-ACCUITESSA-N n,n,1-trimethyl-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxamide Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C(=O)N(C)C)N(C)CC1 QGBKOCWAAJUPEH-ACCUITESSA-N 0.000 description 1
QUOIKPPBKHYUKB-ZRDIBKRKSA-N n,n-dimethyl-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]-1-(pyridine-4-carbonyl)piperazine-2-carboxamide Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C(=O)N(C)C)N(C(=O)C=2C=CN=CC=2)CC1 QUOIKPPBKHYUKB-ZRDIBKRKSA-N 0.000 description 1
BUDJFUMTWGFUAL-VQHVLOKHSA-N n-[1-[(e)-3-[4-(2-bromophenyl)sulfanyl-3-chlorophenyl]prop-2-enoyl]pyrrolidin-3-yl]acetamide Chemical compound C1C(NC(=O)C)CCN1C(=O)\C=C\C(C=C1Cl)=CC=C1SC1=CC=CC=C1Br BUDJFUMTWGFUAL-VQHVLOKHSA-N 0.000 description 1
KNZTTYVMMLOCSM-XYOKQWHBSA-N n-cyclopropyl-1-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-2-carboxamide Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1C(C(=O)NC2CC2)CNCC1 KNZTTYVMMLOCSM-XYOKQWHBSA-N 0.000 description 1
QNPSGQWAWDUUBG-PKNBQFBNSA-N n-methyl-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C QNPSGQWAWDUUBG-PKNBQFBNSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BGDKULHYNAIZMW-ZRDIBKRKSA-N prop-1-en-2-yl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CCN(C(=O)OC(C)=C)CC1 BGDKULHYNAIZMW-ZRDIBKRKSA-N 0.000 description 1
AIOKATZJHOUORG-ZRDIBKRKSA-N propan-2-yl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=CC=C1C(C)C AIOKATZJHOUORG-ZRDIBKRKSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
IXHDPEAYAVCVPO-FYWRMAATSA-N tert-butyl 2-(dimethylcarbamoyl)-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(C(=O)N(C)C)N(C(=O)OC(C)(C)C)CC1 IXHDPEAYAVCVPO-FYWRMAATSA-N 0.000 description 1
PWDJNUBOGPFZCV-ACCUITESSA-N tert-butyl 2-(hydroxymethyl)-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CC(CO)N(C(=O)OC(C)(C)C)CC1 PWDJNUBOGPFZCV-ACCUITESSA-N 0.000 description 1
UBBUBGSWOSFQIC-WEVVVXLNSA-N tert-butyl 2-[4-[(e)-3-[4-(2,4-dichlorophenyl)sulfanyl-3-nitrophenyl]prop-2-enoyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=C(Cl)C=C1Cl UBBUBGSWOSFQIC-WEVVVXLNSA-N 0.000 description 1
SQPVEGCMIDHZLW-ACCUITESSA-N tert-butyl 3-(hydroxymethyl)-4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1C(CO)CN(C(=O)OC(C)(C)C)CC1 SQPVEGCMIDHZLW-ACCUITESSA-N 0.000 description 1
JHCKSBKEFNSHNW-ACCUITESSA-N tert-butyl 3-[[(e)-3-[4-(2-ethoxyphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]amino]-4-hydroxypyrrolidine-1-carboxylate Chemical compound CCOC1=CC=CC=C1SC(C(=C1)C(F)(F)F)=CC=C1\C=C\C(=O)NC1C(O)CN(C(=O)OC(C)(C)C)C1 JHCKSBKEFNSHNW-ACCUITESSA-N 0.000 description 1
PEZIGBVULRQTAW-ACCUITESSA-N tert-butyl 4-[(e)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC=CC=C1SC(C(=C1)[N+]([O-])=O)=CC=C1\C=C\C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 PEZIGBVULRQTAW-ACCUITESSA-N 0.000 description 1
JVTOUIOBVIEMAU-WEVVVXLNSA-N tert-butyl 4-[(e)-3-[4-(2,4-dichlorophenyl)sulfanyl-3-nitrophenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1[N+]([O-])=O)=CC=C1SC1=CC=C(Cl)C=C1Cl JVTOUIOBVIEMAU-WEVVVXLNSA-N 0.000 description 1
GSHNKTZTTJXKRB-PKNBQFBNSA-N tert-butyl 4-[(e)-3-[4-(2-bromophenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1Br GSHNKTZTTJXKRB-PKNBQFBNSA-N 0.000 description 1
LJPANGPMUCWGGO-WYMLVPIESA-N tert-butyl 4-[(e)-3-[4-(2-piperidin-1-ylphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1N1CCCCC1 LJPANGPMUCWGGO-WYMLVPIESA-N 0.000 description 1
QTMANBNICZSOQM-ACCUITESSA-N tert-butyl 4-[(e)-3-[4-(2-pyrrolidin-1-ylphenyl)sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1N1CCCC1 QTMANBNICZSOQM-ACCUITESSA-N 0.000 description 1
VQTBSWNYGYAVGY-ZRDIBKRKSA-N tert-butyl 4-[(e)-3-[4-[2-(azetidin-1-yl)phenyl]sulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1N1CCC1 VQTBSWNYGYAVGY-ZRDIBKRKSA-N 0.000 description 1
SPYITBAMRZUMPM-ZRDIBKRKSA-N tert-butyl 4-[(e)-3-[4-phenylsulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)\C=C\C(C=C1C(F)(F)F)=CC=C1SC1=CC=CC=C1 SPYITBAMRZUMPM-ZRDIBKRKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
GHVDDXYWODWBQU-UHFFFAOYSA-N trifluoromethanesulfonic acid;hydrobromide Chemical compound [H+].[Br-].OS(=O)(=O)C(F)(F)F GHVDDXYWODWBQU-UHFFFAOYSA-N 0.000 description 1

JP2000609392A 1999-04-02 2000-04-03 細胞接着阻害抗炎症および免疫抑制化合物 Ceased JP2004513063A (ja)