3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionic acid methyl ester | 849059-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionic acid methyl ester
• 英文别名: methyl 3-[1-(3-hydroxypropyl)-2-(2-methylpropyl)benzimidazol-5-yl]propanoate
• CAS: 849059-69-4
• 化学式: C₁₈H₂₆N₂O₃
• 分子量: 318.416
• InChiKey: XHVRBWWWTFNARU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionic acid methyl ester 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N-hydroxy-3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionamide
  参考文献：
  名称：

  N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: Design, synthesis, SAR studies, and in vivo antitumor activity

  摘要：

  A series of N-hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides were designed and synthesized as novel HDAC inhibitors. General SAR has been established for the substituents at positions 1 and 2, as well as the importance of the ethylene group and its attachment to position 5. Optimized compounds are much more potent than SAHA in both enzymatic and cellular assays. A representative compound, 23 (SB639), has demonstrated antitumor activity in a colon cancer xenograft model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.041
• 作为产物：
  描述：

  3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-acrylic acid methyl ester 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionic acid methyl ester
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE DERIVATES: PREPARATION AND PHARMACEUTICAL APPLICATIONS
  [FR] DERIVES DE BENZIMIDAZOLE: PREPARATION ET COMPOSITIONS PHARMACEUTIQUES

  摘要：

  本发明涉及羟肟酸酯化合物，这些化合物是组蛋白去乙酰化酶的抑制剂。更具体地说，本发明涉及含苯并咪唑的化合物及其制备方法。这些化合物可能用作治疗增生性疾病以及涉及组蛋白去乙酰化酶（HDAC）失调的其他疾病的药物。

  公开号：

  WO2005028447A1

文献信息

• Benzimidazole derivates: preparation and pharmaceutical applications
  申请人：Chen Dizhong

  公开号：US20070043043A1

  公开（公告）日：2007-02-22

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to benzimidazole containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with dysregulation of histone deacetylase (HDAC).

  本发明涉及羟肟酸化合物，其为组蛋白去乙酰化酶的抑制剂。更具体地，本发明涉及含苯并咪唑的化合物及其制备方法。这些化合物可能作为药物用于治疗增殖性疾病以及其他涉及组蛋白去乙酰化酶（HDAC）失调或相关的疾病。
• Benzimidazole derivatives: preparation and pharmaceutical applications
  申请人：S*BIO Pte Ltd.

  公开号：US07781595B2

  公开（公告）日：2010-08-24

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to benzimidazole containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with dysregulation of histone deacetylase (HDAC).

  本发明涉及羟肟酸化合物，其为组蛋白去乙酰化酶抑制剂。更具体地，本发明涉及含苯并咪唑的化合物及其制备方法。这些化合物可能作为药物用于治疗增殖性疾病以及涉及、与组蛋白去乙酰化酶（HDAC）失调相关的其他疾病。
• BENZIMIDAZOLE DERIVATIVES: PREPARATION AND PHARMACEUTICAL APPLICATIONS
  申请人：Chen Dizhong

  公开号：US20100256138A1

  公开（公告）日：2010-10-07

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to benzimidazole containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with dysregulation of histone deacetylase (HDAC).

  本发明涉及羟肟酸类化合物，这些化合物是组蛋白去乙酰化酶的抑制剂。更具体地说，本发明涉及含苯并咪唑的化合物及其制备方法。这些化合物可能作为药物用于治疗增殖性疾病以及与组蛋白去乙酰化酶（HDAC）失调有关的其他疾病。
• BENZIMIDAZOLE DERIVATES: PREPARATION AND PHARMACEUTICAL APPLICATIONS
  申请人：S*Bio Pte Ltd

  公开号：EP1673349A1

  公开（公告）日：2006-06-28
• EP1673349A4
  申请人：——

  公开号：EP1673349A4

  公开（公告）日：2008-01-23