methyl 2-cyano-5-(methylthio)benzoate | 127510-97-8

• 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: methyl 2-cyano-5-(methylthio)benzoate
• 英文别名: methyl 2-cyano-5-methylsulfanylbenzoate
• CAS: 127510-97-8
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: FWKGCZVSYOPIEV-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  373.4±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-cyano-5-(methylthio)benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.17h， 生成 ethyl (2Z)-2-cyano-2-(5-methylsulfanyl-3-oxoisoindol-1-ylidene)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：

  methyl 2-chloro-5-(methylthio)benzoate 、 氰化亚铜 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以28%的产率得到methyl 2-cyano-5-(methylthio)benzoate
  参考文献：
  名称：

  WO2006/67462

  摘要：

  公开号：

文献信息

• 1-6-Substituted (3R,6R)-3-(2,3-Dihydro-1H-Inden-2-Yl)-2,5-Piperazinedione Derivatives as Oxytocin Receptor Antagonists For the Treatment of Preterm Labour, Dysmenorrhea and Endometriosis
  申请人：Leach Colin Andrew

  公开号：US20080242666A1

  公开（公告）日：2008-10-02

  The present invention relates to Compound S of Formula (I).

  本发明涉及化合物S，其化学式为（I）。
• 1,6-SUBSTITUTED (3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-2,5-PIPERAZINEDIONE DERIVATIVES AS OXYTOCIN RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PRE-TERM LABOUR, DYSMENORRHEA AND ENDOMETRIOSIS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1831183A1

  公开（公告）日：2007-09-12
• [EN] 1,6 - SUBSTITUTED (3R,6R) -3- (2,3-DIHYDRO-1H-INDEN-2-YL)-2,5-PIPERAZINEDIONE DERIVATIVES AS OXYTOCIN RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PRE-TERM LABOUR, DYSMENORRHEA AND ENDOMETRIOSIS<br/>[FR] DERIVES DE 1,6-SUBSTITUES DE LA (3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-2,5-PIPERAZINEDIONE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR DE L'OXYTOCINE POUR LE TRAITEMENT DE L'ACCOUCHEMENT PREMATURE, DE LA DYSMENORRHEE ET DE L'ENDOMETRIOSE
  申请人：GLAXO GROUP LTD

  公开号：WO2006067462A1

  公开（公告）日：2006-06-29

  [EN] The present invention relates to compound S of Formula (I).
  [FR] La présente invention concerne le composé S de formule (I).
• 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.
• WO2006/67462
  申请人：——

  公开号：——

  公开（公告）日：——