2-cyano-4,5-dichlorobenzoic acid methyl ester | 71969-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-4,5-dichlorobenzoic acid methyl ester
• 英文别名: 4,5-Dichlor-2-cyanbenzoesaeuremethylester；2-Cyano-4,5-dichlorobenzoic Acid, Methyl Ester；methyl 4,5-dichloro-2-cyanobenzoate
• CAS: 71969-20-5
• 化学式: C₉H₅Cl₂NO₂
• 分子量: 230.05
• InChiKey: SVHFLKHSMSIMPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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-cyano-4,5-dichlorobenzoic acid methyl ester 在 氨 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.17h， 生成 Ethyl 2-cyano-2-(5,6-dichloro-1-cyano-2-methyl-3-oxoisoindol-1-yl)acetate
  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-carbamoyl-4,5-dichlorobenzoic acid 以97%的产率得到
  参考文献：
  名称：

  WROBEL, JAY E.

  摘要：

  DOI：

文献信息

• Novel spirosuccinimides as aldose reductase inhibitors and
  申请人：American Home Products Corporation

  公开号：US04946858A1

  公开（公告）日：1990-08-07

  This invention relates to novel spirosuccinimide derivatives, to the processes for their preparation, to methods for using the compounds, and to pharmaceutical preparations thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  本发明涉及新颖的螺内酰亚胺衍生物，其制备过程，使用这些化合物的方法以及其制备的制药制剂。这些化合物具有药物特性，使它们有益于治疗糖尿病及其相关疾病。
• DE2903709
  申请人：——

  公开号：——

  公开（公告）日：——
• US4231931A
  申请人：——

  公开号：US4231931A

  公开（公告）日：1980-11-04
• US4317929A
  申请人：——

  公开号：US4317929A

  公开（公告）日：1982-03-02