5-(Pyrrolidin-1-yl)thiophene-2-carboxylic acid | 623588-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(Pyrrolidin-1-yl)thiophene-2-carboxylic acid
• 英文别名: 5-pyrrolidin-1-ylthiophene-2-carboxylic acid
• CAS: 623588-22-7
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: OXYPNKLLDBWKET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-amino-1-(3-amino-3-oxopropyl)-1H-benzimidazol-5-yl]-N-methylbenzamide 、 5-(Pyrrolidin-1-yl)thiophene-2-carboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[(2E)-5-[benzene(methyl)amido]-1-(2-carbamoylethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-ylidene]-5-(pyrrolidin-1-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  Discovery of potent inhibitors of interleukin-2 inducible T-cell kinase (ITK) through structure-based drug design

  摘要：

  Interleukin-2 inducible T-cell kinase (ITK) is a member of the Tec kinase family and is involved with T-cell activation and proliferation. Due to its critical role in acting as a modulator of T-cells, ITK inhibitors could provide a novel route to anti-inflammatory therapy. This work describes the discovery of ITK inhibitors through structure-based design where high-resolution crystal structural information was used to optimize interactions within the kinase specificity pocket of the enzyme to improve both potency and selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.028
• 作为产物：
  描述：

  氢氧化锂 、 N-(2-Aminophenyl)-5-(piperidin-1-yl)thiophene-2-carboxamide 在 氮 、 甲醇 、 乙醚 、 乙酸乙酯 、 Sodium sulfate-III 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以to give the title compound (262 mg, 66%)的产率得到5-(Pyrrolidin-1-yl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Inhibitors of histone deacetylase

  摘要：

  本发明涉及式(I)的化合物；其中环A是杂环基；m为0-4，每个R1为羟基、卤素、三氟甲基和氰基等基团；环B是噻吩基、噻二唑基、噻唑基、嘧啶基、吡嗪基、吡啶并嘧啶基和吡啶基等环基；R2为卤素，n为0-2；每个R4为羟基、卤素、三氟甲基和氰基等基团；p为0-4；R3为氨基或羟基；或其药学上可接受的盐或体内可水解的酯或酰胺；其制备方法、含有它们的制药组合物以及它们在治疗组织脱乙酰化酶介导的疾病或医学状况中的应用。

  公开号：

  US20050222410A1

文献信息

• INHIBITORS OF HISTONE DEACETYLASE
  申请人：Astrazeneca AB

  公开号：EP1501508A1

  公开（公告）日：2005-02-02
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：ASTRAZENECA AB

  公开号：WO2003092686A1

  公开（公告）日：2003-11-13

  The invention concerns a compound of the formula (I); wherein Ring A is heterocyclyl; m is 0-4 and each R1 is a group such as hydroxy, halo, trifluoromethyl and cyano; Ring B is ring such as thienyl, thiadiazolyl, thiazolyl, pyrimidyl, pyrazinyl, pyridazinyl and pyridyl; R2 is halo and n is 0-2; and each R4 is a group such as hydroxy, halo, trifluoromethyl and cyano; p is 0-4; and R3 is amino or hydroxy; or pharmaceutically-acceptable salts or in-vivo-hydrolysable ester or amide thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical condions mediated by histone deacetylase.