<2-(5-chlorobenzothienyl)>acetonitrile | 23799-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: <2-(5-chlorobenzothienyl)>acetonitrile
• 英文别名: 2-(5-Chloro-1-benzothiophen-2-yl)acetonitrile
• CAS: 23799-62-4
• 化学式: C₁₀H₆ClNS
• 分子量: 207.683
• InChiKey: YNCZNRXWKPDARA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <2-(5-chlorobenzothienyl)>acetonitrile 在 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 生成 1-(5-Chlorobenzo[b]thien-2-yl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  [EN] N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS
  [FR] DÉRIVÉS N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE UTILES EN TANT QU'INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE

  摘要：

  本处描述的是公式I的化合物，制造此类化合物的方法，包含此类化合物的药物组合物和药品，以及用于治疗或预防与葡萄糖苷鞘氨醇合酶（GCS）相关疾病的I化合物。

  公开号：

  WO2015065937A1
• 作为产物：
  描述：

  5-chloro-2-methylbenzo[b]thiophene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基硫酸氢铵 作用下， 以 四氯化碳 、 氯仿 、 水 为溶剂， 反应 25.5h， 生成 <2-(5-chlorobenzothienyl)>acetonitrile
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002

文献信息

• N-(1-hydroxy-3-(pyrrolidinyl)propan-2-yl)pyrrolidine-3-carboxamide derivatives as glucosylceramide synthase inhibitors
  申请人：BIOMARIN PHARMACEUTICAL INC.

  公开号：US10239832B2

  公开（公告）日：2019-03-26

  Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and compounds I for use to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

  本文描述了式 I 化合物、制造此类化合物的方法、含有此类化合物的药物组合物和药物，以及用于治疗或预防与葡萄糖酰胺合成酶 (GCS) 相关的疾病或病症的式 I 化合物。
• N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS
  申请人：BioMarin Pharmaceutical Inc.

  公开号：EP3063141B1

  公开（公告）日：2018-02-28
• [EN] N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS<br/>[FR] DÉRIVÉS N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE UTILES EN TANT QU'INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE
  申请人：BIOMARIN PHARM INC

  公开号：WO2015065937A1

  公开（公告）日：2015-05-07

  Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and compounds I for use to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

  本处描述的是公式I的化合物，制造此类化合物的方法，包含此类化合物的药物组合物和药品，以及用于治疗或预防与葡萄糖苷鞘氨醇合酶（GCS）相关疾病的I化合物。
• Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Thomas R. Alessi、Terence M. Dolak、Thomas T. Nguyen、John D. Tomer、Frieda Guzzo、Jehan F. Bagli、Michael L. McCaleb

  DOI：10.1021/jm00085a002

  日期：1992.4

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).