CN101423503A - 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-carbomethoxyl cyclopropane)-1,3-benzopyrene and synthetic method thereof - Google Patents

2-(trans-2,3-dihydro-2-aryl-1-cyano-3-carbomethoxyl cyclopropane)-1,3-benzopyrene and synthetic method thereof Download PDF

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CN101423503A
CN101423503A CNA2008102039941A CN200810203994A CN101423503A CN 101423503 A CN101423503 A CN 101423503A CN A2008102039941 A CNA2008102039941 A CN A2008102039941A CN 200810203994 A CN200810203994 A CN 200810203994A CN 101423503 A CN101423503 A CN 101423503A
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benzothiazole
cyano
cyclopropane
trans
dihydro
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刘颖
任仲皎
曹卫国
童玮琦
陈杰
陆叶营
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University of Shanghai for Science and Technology
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Abstract

The invention relates to 2-(trans-2, 3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, 3-benzothiazole and a synthesizing method thereof. The structural formula of the compound is shown as the right. The method is to replace ethylene-1, 3-benzothiazole, triphenylarsine and methyl bromoacetate by 2-cyanoaryl available as a raw material to synthesize the target product by one kettle method. The method has the advantages of simple and convenient operation, higher yield and the like, and provides an effective path for synthesis of natural products.

Description

2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1,3-benzothiazole and synthetic method thereof
Technical field
The present invention relates to a kind of 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1,3-benzothiazole and synthetic method thereof.
Background technology
The research of cyclopropanes compound has occupied extremely important status in the research preparation of biological organic synthesis and medicine and agricultural chemicals.Recently, research finds that more and more the cyclopropane groups decorating molecule can improve the pharmacologically active of molecule greatly, and all have the cyclopropane structural unit in a lot of natural compoundss, therefore the research that cyclopropane is introduced on the compound that biology or pharmacologically active are arranged has caused everybody extensive concern.
Heterocyclic system has great importance in the compound molecule that biological and pharmacologically active are arranged, and has had been found that many clinical values that have in the research and development of new drug.Therefore people's a large amount of research now contains the heterocyclic system of cyclopropane, though found many successful synthetic methods, highly-solid selectively synthesizes them efficiently and is still the emphasis of research.
Summary of the invention:
One of purpose of the present invention is to provide a kind of 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1,3-benzothiazole.
Two of purpose of the present invention is to provide the preparation method of this compound.
For achieving the above object, the reaction mechanism that the inventive method adopts is:
Figure A200810203994D00031
Wherein, Ar is 4-CH 3OC 6H 4, 4-CH 3C 6H 4, C 6H 5, 4-FC 6H 4,, 4-ClC 6H 4,, 3-ClC 6H 4, 2-ClC 6H 4,, 3-NO 2C 6H 4, 2,4-CH 3OC 6H 3Or 3,4-CH 3OC 6H 3
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole is characterized in that the structural formula of this compound is:
Figure A200810203994D00032
Wherein, Ar is 4-CH 3OC 6H 4, 4-CH 3C 6H 4, C 6H 5, 4-FC 6H 4,, 4-ClC 6H 4,, 3-ClC 6H 4, 2-ClC 6H 4,, 3-NO 2C 6H 4, 2,4-CH 3OC 6H 3Or 3,4-CH 3OC 6H 3
A kind of above-mentioned 2-(trans-2 for preparing, 3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the method of 3-benzothiazole, the concrete steps that it is characterized in that this method are: with 2-cyano-aryl substituted ethylene-1, the 3-benzothiazole, triphenylarsine, methyl bromoacetate and sodium bicarbonate are by 1:(0.09～0.11): (1.1～1.3): the mol ratio of (2.9～3.1) is dissolved in the second cyanogen, stirring and refluxing is reacted to 2-cyano-aryl substituted ethylene-1, the 3-benzothiazole reacts completely, remove and desolvate, column chromatography for separation obtains 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole; Described 2-cyano-aryl substituted ethylene-1, the structural formula of 3-benzothiazole is:
Figure A200810203994D00041
Wherein, Ar is 4-CH 3OC 6H 4, 4-CH 3C 6H 4, C 6H 5, 4-FC 6H 4,, 4-ClC 6H 4, 3-ClC 6H 4, 2-ClC 6H 4,, 3-NO 2C 6H 4, 2,4-CH 3OC 6H 3Or 3,4-CH 3OC 6H 3
Thinking that theoretically the trans-cyclopropane benzothiazole derivant that the present invention obtains can be used for biological medicine, is the fine bioactive structural unit of a kind of tool.The inventive method method of the present invention is the 2-cyano-aryl substituted ethylene-1 to be easy to get, 3-benzothiazole, triphenylarsine, methyl bromoacetate are raw material, and one kettle way synthesizes target product, have easy and simple to handle, productive rate is synthetic kind of the valid approach that provides of natural product than advantages such as height.
Embodiment
The concrete steps of reaction are: with 2-cyano-aryl substituted ethylene-1,3-benzothiazole, triphenylarsine, methyl bromoacetate and sodium bicarbonate are by 1:(0.09～0.11): (1.1～1.3): the mol ratio of (2.9～3.1) is dissolved in the second cyanogen, stirring and refluxing is reacted to 2-cyano-aryl substituted ethylene-1, the 3-benzothiazole reacts completely, remove and desolvate, column chromatography for separation obtains 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1,3-benzothiazole.
Embodiment one: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00042
Wherein Ar is 4-CH 3OC 6H 4, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-(4-methoxyphenyl) cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00051
Molecular formula: C 20H 16N 2O 3S
Molecular weight: 364.0882
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.27 (d, J=8.0Hz, 1H, CH), 3.64 (s, 3H, OCH 3), 3.83 (s, 3H, OCH 3), 4.09 (d .J=8.0Hz, 1H, CH), 7.00 (d, J=8.6Hz, 2H, Ar-H), 7.35 (d, J=8.5Hz, 2H, Ar-H), 7.44-7.50 (dt, J=8.0,8.3Hz, 2H, Ar-H), 7.89 (d, J=7.8Hz, 1H, Ar-H), 8.04 (d, J=8.0Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13036,2239,1730,1518.
Mass spectrum m/z:364 (M +, 16), 305 (100), 306 (22), 261 (15), 278 (10), 290 (10), 290 (9), 289 (9), 274 (8)
Ultimate analysis: C, 65.79; H, 4.43; N, 7.66.
Embodiment two: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00052
Wherein Ar is 4-CH 3C 6H 4, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-(4-tolyl)-cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00053
Molecular formula: C 20H 16N 2O 2S
Molecular weight: 348.0932
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 2.37 (s, 3H, CH 3), 3.30 (d, J=8.0Hz, 1H, CH), 3.64 (s, 3H, OCH 3), 4.10 (d, J=8.0Hz, 1H, CH), 7.24 (d, J=7.6Hz, 2H, Ar-H), 7.32 (d, J=7.9Hz, 2H, Ar-H), 7.41-7.46 (t, J=7.5Hz, 1H, Ar-H), 7.49-7.54 (t, J=7.5Hz, 1H, Ar-H), 7.88 (d, J=7.6Hz, 1H, Ar-H), 8.04 (d, J=7.6Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13031,2238,1754,1516.Anal.Calcd.for C 20H 16N 2O 2S:C, 68.95; H, 4.63; N, 8.04.Found:C, 68.93; H, 4.61; N, 8.05.
Mass spectrum m/z:348 (M +, 12), 289 (100), 290 (21), 262 (20), 274 (15), 288 (6), 291 (6) 127 (5)
Ultimate analysis: C, 68.93; H, 4.61; N, 8.05.
Embodiment three: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Wherein Ar is C 6H 5, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-benzyl ring propane)-1, the 3-benzothiazole, and its structural formula is:
Molecular formula: C 19H 14N 2O 2S
Molecular weight: 334.0776
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.33 (d, J=8.0Hz, 1H, CH), 3.66 (s, 3H, OCH 3), 4.17 (d, J=8.2Hz, 1H, CH), 7.40-7.55 (m, 7H, Ar-H), 7.90 (d, J=7.7Hz, 1H, Ar-H); 8.06 (d, J=7.8Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13030,2240,1746,1513.
Mass spectrum m/z:334 (M +, 6), 275 (100), 276 (21), 248 (21), 40 (13), 140 (13), 59 (11) 274 (10), 205 (10)
Ultimate analysis: C, 68.25; H, 4.22; N, 8.39.
Embodiment four: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00071
Wherein Ar is 4-FC 6H 4, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-2-(4-fluorophenyl)-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00072
Molecular formula: C 19H 13FN 2O 2S
Molecular weight: 352.0682
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.28 (d, J=8.0Hz, 1H, CH), 3.65 (s, 3H, OCH 3), 4.13 (d, J=8.0Hz, 1H, CH), 7.11-7.16 (t, J=7.1Hz, 2H, Ar-H), and 7.40-7.44 (m, 3H, Ar-H), 747-7.55 (m, 1H, Ar-H), 7.73 (d, J=7.8Hz, 1H, Ar-H), 8.05 (d, J=8.0Hz, 1H, Ar-H) infrared absorption (KBr) cm -13023,2238,1741,1513.
Mass spectrum m/z:352 (M +, 7), 293 (100), 294 (21), 266 (15), 158 (11), 290 (10), 292 (8), 295 (6), 146 (5) ultimate analysis: C, 64.70; H, 3.67; N, 7.92.
Embodiment five: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Wherein Ar is 4-ClC 6H 4, the product that obtains is 2-(trans-2,3-dihydro-2-(4-chloro-phenyl-)-1-cyano group-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00074
Molecular formula: C 19H 13ClN 2O 2S
Molecular weight: 368.0386
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.27 (d, J=8.0Hz, 1H, CH), 3.65 (s, 3H, OCH 3), 4.13 (d, J=8.0Hz, 1H, CH), 7.36-7.45 (m, 4H, Ar-H), 7.47-7.65 (m, 2H, Ar-H), 7.89 (d, J=8.0Hz, 1H, Ar-H), 8.04 (d, J=8.0Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13011,2240,1680,1556.
Mass spectrum m/z:368 (M +, 16), 309 (100), 311 (38), 274 (37), 310 (22), 273 (12), 275 (8), 312 (7)
Ultimate analysis: C, 61.86; H, 3.56; N, 7.54.
Embodiment six: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00081
Wherein Ar is 3-ClC 6H 4, the product that obtains is 2-(trans-2,3-dihydro-2-(3-chloro-phenyl-)-1-cyano group-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole, and its structure is:
Figure A200810203994D00082
Molecular formula: C 19H 13ClN 2O 2S
Molecular weight: 368.0386
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.31 (d, J=8.0Hz, 1H, CH), 3.65 (s, 3H, OCH 3), 4.13 (d, J=8.0Hz, 1H, CH), 7.33-7.56 (m, 6H, Ar-H), 7.90 (d, J=8.0Hz, 1H, Ar-H), 8.05 (d, J=8.0Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13031,2240,1749,1569.
Mass spectrum m/z:368 (M +, 16), 309 (100), 274 (40), 311 (38), 310 (22), 273 (17), 275 (9), 247 (8) ultimate analysis: C, 61.90; H, 3.50; N, 7.52.
Embodiment seven: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00091
Wherein Ar is 2-ClC 6H 4, the product that obtains is 2-(trans-2,3-dihydro-2-(2-chloro-phenyl-)-1-cyano group-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00092
Molecular formula: C 19H 13ClN 2O 2S
Molecular weight: 368.0386
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.34 (d, J=8.0Hz, 1H, CH), 3.69 (s, 3H, OCH 3), 4.11 (d, J=8.0Hz, 1H, CH), 7.33-7.58 (m, 6H, Ar-H), 7.91 (d, J=8.0Hz, 1H, Ar-H), 8.04 (d, J=8.0Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13054,2241,1731,1505.
Mass spectrum m/z:368 (M +, 16), 309 (100), 40 (44), 311 (38), 274 (34), 275 (24), 310 (21), 43 (17), 59 (16)
Ultimate analysis C, 61.92; H, 3.55; N, 7.55.
Embodiment eight: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Wherein Ar is 3-NO 2C 6H 4, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-(3-nitrophenyl) cyclopropane)-1, the 3-benzothiazole, and its structure is:
Figure A200810203994D00094
Molecular formula: C 19H 13N 3O 4S
Molecular weight: 379.0627
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.39 (d, J=8.0Hz, 1H, CH), 3.67 (s, 3H, OCH 3), 4.29 (d, J=8.0Hz, 1H, CH), 7.44-7.57 (m, 2H, Ar-H), 7.64-7.69 (t, J=8.0Hz, 1H, Ar-H), 7.79-7.82 (d, J=7.7Hz, 1H, Ar-H), 7.81 (d, J=8.0Hz, 1H, Ar-H), 8.06 (d, J=8.0Hz, 1H, Ar-H), 8.27-8.33 (t, J=8.0Hz, 2H, Ar-H)
Infrared absorption (KBr) cm -13069,2235,1733,1533.
Mass spectrum m/z:379 (M +, 9), 320 (100), 274 (36), 321 (22), 273 (22), 272 (13), 59 (13) 198 (10)
Ultimate analysis: C, 60.11, H, 3.38, N, 11.07.
Embodiment nine: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Wherein Ar is 2,4-CH 3OC 6H 3, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-(2, the 4-dimethoxy phenyl) cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00102
Molecular formula: C 19H 13N 3O 4S
Molecular weight: 394.0987
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.21 (d, J=7.8Hz, 1H, CH), 3.67 (s, 3H, OCH 3), 3.80 (d, J=8.0Hz, 1H, CH), 3.83 (s, 3H, OCH 3), 3.93 (s, 3H, OCH3), 6.50-6.55 (m, 2H, Ar-H), 7.09-7.12 (d, J=8.2n Hz, 1H, Ar-H), 7.41-7.53 (m, 2H, Ar-H), 7.90 (d, J=8.0Hz, 1H, Ar-H), 8.03 (d, J=8.0Hz, 1H, Ar-H)
Infrared absorption (KBr) cm -13062,2240,1733,1585.
Mass spectrum m/z:205 (100), 40 (97), 335 (74), 43 (45), 309 (27), 275 (24), 41 (22), 176 (19)
Ultimate analysis: 63.71, H, 4.50, N, 7.09.
Embodiment ten: the raw material 2-cyano-aryl substituted ethylene-1 of employing, and the structural formula of 3-benzothiazole is:
Figure A200810203994D00111
Wherein Ar is 3,4-CH 3OC 6H 3, the product that obtains is 2-(trans-2,3-dihydro-1-cyano group-3-methoxycarbonyl-2-(3, the 4-dimethoxy phenyl) cyclopropane)-1, the 3-benzothiazole, and its structural formula is:
Figure A200810203994D00112
Molecular formula: C 19H 13N 3O 4S
Molecular weight: 394.0987
Outward appearance: colorless solid
Proton nmr spectra (300MHz, CDCl 3,, interior mark: TMS) δ 3.29 (d, J=8.0Hz, 1H, CH), 3.67 (s, 3H, OCH 3), 3.91 (s, 3H, OCH 3), 3.94 (s, 3H, OCH 3), 4.10 (d, J=8.0Hz, 1H, CH), 6.90-6.99 (m, 3H, Ar-H), 7.46-7.53 (m, 2H, Ar-H), 7.90 (d, J=7.8Hz, 1H, Ar-H), 8.06 (d, J=8.2Hz, 1H, Ar-H) infrared absorption (KBr) cm -13035,2238,1738,1520.
Mass spectrum m/z:57 (100), 43 (93), 335 (82), 71 (63), 85 (43), 55 (43), 69 (37), 41 (35)
Ultimate analysis: C, 63.88, H, 4.52, N, 7.00.

Claims (2)

1. a 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole is characterized in that the structural formula of this compound is:
Figure A200810203994C00021
Wherein, Ar is 4-CH 3OC 6H 4, 4-CH 3C 6H 4, C 6H 5, 4-FC 6H 4,, 4-ClC 6H 4,, 3-ClC 6H 4, 2-ClC 6H 4,, 3-NO 2C 6H 4, 2,4-CH 3OC 6H 3Or 3,4-CH 3OC 6H 3
2. one kind prepares 2-according to claim 1 (trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the method of 3-benzothiazole, the concrete steps that it is characterized in that this method are: with 2-cyano-aryl substituted ethylene-1, the 3-benzothiazole, triphenylarsine, methyl bromoacetate and sodium bicarbonate are by 1:(0.09～0.11): (1.1～1.3): the mol ratio of (2.9～3.1) is dissolved in the second cyanogen, stirring and refluxing is reacted to 2-cyano-aryl substituted ethylene-1, the 3-benzothiazole reacts completely, remove and desolvate, column chromatography for separation obtains 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-methoxycarbonyl cyclopropane)-1, the 3-benzothiazole; Described 2-cyano-aryl substituted ethylene-1, the structural formula of 3-benzothiazole is:
Figure A200810203994C00022
Wherein, Ar is 4-CH 3OC 6H 4, 4-CH 3C 6H 4, C 6H 5, 4-FC 6H 4,, 4-ClC 6H 4,, 3-ClC 6H 4, 2-ClC 6H 4,, 3-NO 2C 6H 4, 2,4-CH 3OC 6H 3Or 3,4-CH 3OC 6H 3
CNA2008102039941A 2008-12-04 2008-12-04 2-(trans-2,3-dihydro-2-aryl-1-cyano-3-carbomethoxyl cyclopropane)-1,3-benzopyrene and synthetic method thereof Pending CN101423503A (en)

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US11014873B2 (en) 2017-02-03 2021-05-25 Certa Therapeutics Pty Ltd. Anti-fibrotic compounds

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Publication number Priority date Publication date Assignee Title
US9561201B2 (en) 2006-07-05 2017-02-07 Fibrotech Therapeutics Pty Ltd Therapeutic compounds
EP2491030A1 (en) * 2009-10-22 2012-08-29 Fibrotech Therapeutics PTY LTD Fused ring analogues of anti-fibrotic agents
EP2491030A4 (en) * 2009-10-22 2013-04-17 Fibrotech Therapeutics Pty Ltd Fused ring analogues of anti-fibrotic agents
US9062076B2 (en) 2009-10-22 2015-06-23 Fibrotech Therapeutics Pty Ltd Fused ring analogues of anti-fibrotic agents
US9951087B2 (en) 2009-10-22 2018-04-24 Fibrotech Therapeutics Pty Ltd Fused ring analogues of anti-fibrotic agents
US11014873B2 (en) 2017-02-03 2021-05-25 Certa Therapeutics Pty Ltd. Anti-fibrotic compounds
US11603349B2 (en) 2017-02-03 2023-03-14 Certa Therapeutics Pty Ltd Anti-fibrotic compounds

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