2-氰基-5-苯基苯甲酸乙酯 | 127510-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-5-苯基苯甲酸乙酯
• 英文名称: 2-cyano-5-phenylbenzoic acid ethyl ester
• 英文别名: Ethyl 4-cyano[1,1a(2)-biphenyl]-3-carboxylate；ethyl 2-cyano-5-phenylbenzoate
• CAS: 127510-99-0
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: JFEOGBDFIVJLKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  69-74 °C
• 沸点：
  437.9±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氰基-5-苯基苯甲酸乙酯 在 氨 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.17h， 生成 Cyano-[2-methyl-3-oxo-5-phenyl-2,3-dihydro-isoindol-(1Z)-ylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  2-氨基-5-溴苯甲酸乙酯 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 、 sodium nitrite 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 2-氰基-5-苯基苯甲酸乙酯
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016

文献信息

• WROEL, JAY E.
  作者：WROEL, JAY E.

  DOI：——

  日期：——
• US5939437A
  申请人：——

  公开号：US5939437A

  公开（公告）日：1999-08-17
• [EN] CCK AND GASTRIN RECEPTOR LIGANDS<br/>[FR] LIGANDS DE RECEPTEURS DES CHOLECYSTOKININES ET DES GASTRINES
  申请人：JAMES BLACK FOUNDATION LIMITED

  公开号：WO1995030647A1

  公开（公告）日：1995-11-16

  (EN) Compounds of formula (I), wherein Ar is a monocyclic aromatic group, R1 (or each R1 group, when m is 2 or more) is selected from halo, amino, nitro, cyano, sulphamoyl, sulphonyl, trifluoromethyl, C1 to C3 alkyl, C1 to C3 alkylamino, C1 to C3 dialkylamino, phenyl, substituted phenyl, C1 to C3 alkoxy, hydroxy, esterified hydroxy, C1 to C3 hydroxyalkyl, C1 to C3 alkylcarboxyamino, carboxy, esterified carboxy and amidated carboxy; m is from 0 to 4, provided that m is not more than 2 unless R1 is exclusively halo, x + y = 0 or 1, R2 and R4 are independently H, C1 to C3 alkyl or a C1 to C3 alkylene link to an $i(ortho) carbon atom in the aromatic ring, R3 is H or C1 to C15 hydrocarbyl, in which one or more hydrogen atoms of the hydrocarbyl group may be replaced by a halogen atom, and up to two of the carbon atoms may be replaced by a nitrogen, oxygen or sulphur atom, provided that R3 does not contain a -O-O- group, R5 is H or C1 to C3 alkyl, U is aryl, substituted aryl, heterocyclic, substituted heterocyclic or cycloalkyl, and Z is a group of formulae (IIa or IIb) (wherein R6 is H or C1 to C3 alkyl, X is -CO2H, esterified carboxy, amidated carboxy, tetrazolyl, hydroxy, cyano, amidino, -CH2OH, -SO2NHCOR7, -SONHCOR7, -COR7, -NHSO2R7, -CONHSO2R7, -NHCOR7 or -SO2NHR8, in which R7 is alkyl (e.g. C1 to C6 alkyl), haloalkyl (e.g. C1 to C6 haloalkyl), aryl or substituted aryl, and R8 is -OH, -CN, or a group selected from those recited above for R7, Y is H or a group selected from those recited above for X, and a is from 0 to 2) and pharmaceutically acceptable salts thereof are CCK and gastrin receptor ligands.(FR) Composés de formule (I), ainsi que leurs sels acceptables sur le plan pharmacologique, dans laquelle Ar représente un groupe aromatique monocyclique, R1 (ou chaque groupe R1, lorsque m vaut 2 ou davantage) est choisi parmi halo, amino, nitro, cyano, sulfamoyle, sulfonyle, trifluorométhyle, alcoyle C1 à C3, alcoylamino C1 à C3, dialcoylamino C1 à C3, phényle, phényle substitué, alcoxy C1 à C3, hydroxy, hydroxy estérifié, hydroxyalcoyle C1 à C3, alcoylcarboxyamino C1 à C3, carboxy, carboxy estérifié et carboxy amidé, m vaut 0 à 4, à condition que m ne vaille pas plus de 2 si R1 représente exclusivement halo, x + y égalent 0 ou 1, R2 et R4 représentent indépendamment H, alcoyle C1 à C3 ou une liaison alcoylène C1 à C3 dans la position ortho d'un atome de carbone dans le cycle aromatique, R3 représente H ou hydrocarbyle C1 à C15, dans lequel un ou plusieurs atomes d'hydrogène du groupe hydrocarbyle peuvent être remplacés par un atome d'halogène, et jusqu'à deux atomes de carbone peuvent être remplacés par un atome d'azote, d'oxygène ou de soufre, à condition que R3 ne contienne pas un groupe -O-O-, R5 représente H ou alcoyle C1 à C3, U représente aryle, aryle substitué, hétérocyclique, hétérocyclique substitué ou cycloalcoyle et Z représente un groupe de formule (IIa ou IIb) dans laquelle R6 représente -CO2H, carboxy estérifié, carboxy amidé, tétrazolyle, hydroxy, cyano, amidino, -CH2OH, -SO2NHCOR7, -SONHCOR7, -COR7, -NHSO2R7, -CONHSO2R7, -NHCOR7 ou -SO2NHR8, où R7 représente alcoyle (par exemple alcoyle C1 à C6), haloalcoyle (par exemple haloalcoyle C1 à C6), aryle ou aryle substitué, et R8 représente -OH, -CN, ou un groupe choisi parmi ceux cités pour R7, Y représente H ou un groupe choisi parmi ceux cités pour X, et a vaut 0 à 2. Ces composés sont des ligands de récepteurs des cholécystokinines et des gastrines.
• Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents
  作者：Jay Wrobel、Arlene Dietrich、Shiela A. Woolson、Jane Millen、Michael McCaleb、Maria C. Harrison、Thomas C. Hohman、Janet Sredy、Donald Sullivan

  DOI：10.1021/jm00102a016

  日期：1992.11

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.