CA2048001A1 - 1-hydroxyindoles a substitution en 2 - Google Patents
1-hydroxyindoles a substitution en 2Info
- Publication number
- CA2048001A1 CA2048001A1 CA 2048001 CA2048001A CA2048001A1 CA 2048001 A1 CA2048001 A1 CA 2048001A1 CA 2048001 CA2048001 CA 2048001 CA 2048001 A CA2048001 A CA 2048001A CA 2048001 A1 CA2048001 A1 CA 2048001A1
- Authority
- CA
- Canada
- Prior art keywords
- cyano
- hydroxy
- indole
- group
- compound
- Prior art date
- 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.)
- Abandoned
Links
- -1 2-substituted-1-hydroxyindoles Chemical class 0.000 title claims abstract description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 29
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- MNBZUVGXWZGKRD-UHFFFAOYSA-N 6-chloro-1-hydroxy-2-(4-nitrophenyl)indole-3-carbonitrile Chemical compound N#CC=1C2=CC=C(Cl)C=C2N(O)C=1C1=CC=C([N+]([O-])=O)C=C1 MNBZUVGXWZGKRD-UHFFFAOYSA-N 0.000 claims description 3
- KUTKNBCXXRYTMC-UHFFFAOYSA-N 6-chloro-1-hydroxy-2-phenylindole-3-carbonitrile Chemical compound N#CC=1C2=CC=C(Cl)C=C2N(O)C=1C1=CC=CC=C1 KUTKNBCXXRYTMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Chemical group 0.000 claims description 3
- QCQKGTFNCCMAIV-UHFFFAOYSA-N 1-hydroxy-2-[3-(trifluoromethyl)phenyl]indole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=CC(C(F)(F)F)=C1 QCQKGTFNCCMAIV-UHFFFAOYSA-N 0.000 claims description 2
- COSOGHVVOHLZEM-UHFFFAOYSA-N 1-hydroxy-2-pyridin-2-ylindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=CC=N1 COSOGHVVOHLZEM-UHFFFAOYSA-N 0.000 claims description 2
- WVTOSADCDDJFEY-UHFFFAOYSA-N 1-hydroxy-2-pyridin-4-ylindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=NC=C1 WVTOSADCDDJFEY-UHFFFAOYSA-N 0.000 claims description 2
- NTNCOGFJGUSLDN-UHFFFAOYSA-N 2-(2-formylphenyl)-1-hydroxyindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=CC=C1C=O NTNCOGFJGUSLDN-UHFFFAOYSA-N 0.000 claims description 2
- JDBSZSREIBLLNQ-UHFFFAOYSA-N 2-(furan-2-yl)-1-hydroxyindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=CO1 JDBSZSREIBLLNQ-UHFFFAOYSA-N 0.000 claims description 2
- JQQPXHBGNLBSCD-UHFFFAOYSA-N 2-ethenyl-1-hydroxyindole-3-carbonitrile Chemical compound C1=CC=C2N(O)C(C=C)=C(C#N)C2=C1 JQQPXHBGNLBSCD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZXSPLEOWPRDGSI-UHFFFAOYSA-N 5,6-dichloro-1-hydroxy-2-phenylindole-3-carbonitrile Chemical compound N#CC=1C2=CC(Cl)=C(Cl)C=C2N(O)C=1C1=CC=CC=C1 ZXSPLEOWPRDGSI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- TXDKDAKBQCOQDD-UHFFFAOYSA-N 1-hydroxy-2-[4-(hydroxyiminomethyl)phenyl]indole-3-carbonitrile Chemical compound C1=CC(C=NO)=CC=C1C1=C(C#N)C2=CC=CC=C2N1O TXDKDAKBQCOQDD-UHFFFAOYSA-N 0.000 claims 1
- CCMKUQNCUXZGLI-UHFFFAOYSA-N 2-(3,4-dimethoxybenzoyl)-1-hydroxyindole-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C1=C(C#N)C2=CC=CC=C2N1O CCMKUQNCUXZGLI-UHFFFAOYSA-N 0.000 claims 1
- UXWLFODUOVHWHX-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-hydroxyindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=C(F)C=C1 UXWLFODUOVHWHX-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 6
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- JUGQARWTQZEZRI-UHFFFAOYSA-N ethyl 2-cyano-2-(2-nitrophenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=CC=CC=C1[N+]([O-])=O JUGQARWTQZEZRI-UHFFFAOYSA-N 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- FSEVOXNEAYNPRA-UHFFFAOYSA-N 1-hydroxy-2-phenylindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=CC=C1 FSEVOXNEAYNPRA-UHFFFAOYSA-N 0.000 description 2
- IJLKADPQWIRZCU-UHFFFAOYSA-N 2-benzoyl-1-hydroxyindole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C(=O)C1=CC=CC=C1 IJLKADPQWIRZCU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IKSNDOVDVVPSMA-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CBr)C=C1 IKSNDOVDVVPSMA-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- QSIOIOLLRSZDFF-UHFFFAOYSA-N 1-hydroxy-2-[4-(trifluoromethyl)phenyl]indole-3-carbonitrile Chemical compound N#CC=1C2=CC=CC=C2N(O)C=1C1=CC=C(C(F)(F)F)C=C1 QSIOIOLLRSZDFF-UHFFFAOYSA-N 0.000 description 1
- WAKHLWOJMHVUJC-UHFFFAOYSA-N 2-hydroxyimino-1,2-diphenylethanol Chemical class C=1C=CC=CC=1C(=NO)C(O)C1=CC=CC=C1 WAKHLWOJMHVUJC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001385948 Pythium sp. Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- OCWHMJVGSFIXBJ-UHFFFAOYSA-N ethyl 2-(6-cyano-6-nitrocyclohexa-2,4-dien-1-yl)acetate Chemical compound CCOC(=O)CC1C=CC=CC1(C#N)[N+]([O-])=O OCWHMJVGSFIXBJ-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56299790A | 1990-08-06 | 1990-08-06 | |
| US562,997 | 1990-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2048001A1 true CA2048001A1 (fr) | 1992-02-07 |
Family
ID=24248653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2048001 Abandoned CA2048001A1 (fr) | 1990-08-06 | 1991-07-26 | 1-hydroxyindoles a substitution en 2 |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2048001A1 (fr) |
-
1991
- 1991-07-26 CA CA 2048001 patent/CA2048001A1/fr not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |