2-cyclopropyl-1H-benzimidazole-4-carboxylic acid | 1339709-22-6

• 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: 2-cyclopropyl-1H-benzimidazole-4-carboxylic acid
• 英文别名: 2-cyclopropyl-1H-1,3-benzodiazole-4-carboxylic acid
• CAS: 1339709-22-6
• 化学式: C₁₁H₁₀N₂O₂
• mdl: MFCD17273097
• 分子量: 202.213
• InChiKey: JVDNIHOFKIDFQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(aminomethyl)piperidin-1-yl)-3-(4-(methylsulfonyl)piperazin-1-yl)propan-2-ol 、 2-cyclopropyl-1H-benzimidazole-4-carboxylic acid 在 1-羟基苯并三唑 、 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， 生成 2-cyclopropyl-N-[[1-[2-hydroxy-3-(4-methylsulfonylpiperazin-1-yl)propyl]piperidin-4-yl]methyl]-1H-benzimidazole-4-carboxamide
  参考文献：
  名称：

  Discovery of TD-8954, a clinical stage 5-HT4 receptor agonist with gastrointestinal prokinetic properties

  摘要：

  The discovery of a series of 5-HT4 receptor agonists based on a novel 2-alkylbenzimidazole aromatic core is described. Optimization of the 2-substituent of the benzimidazole ring led to a series of agonists with subnanomolar binding affinity and moderate-to-high intrinsic activity relative to that of 5-HT. Consistent with our previously described multivalent design approach to this target, subsequent optimization of the linker and secondary binding group regions of the series afforded compound 18 (TD-8954), a potent and selective 5-HT4 receptor agonist in vitro with demonstrated prokinetic activity in multiple species. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.018
• 作为产物：
  描述：

  methyl 2-cyclopropyl-1H-benzimidazole-4-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 生成 2-cyclopropyl-1H-benzimidazole-4-carboxylic acid
  参考文献：
  名称：

  Discovery of TD-8954, a clinical stage 5-HT4 receptor agonist with gastrointestinal prokinetic properties

  摘要：

  The discovery of a series of 5-HT4 receptor agonists based on a novel 2-alkylbenzimidazole aromatic core is described. Optimization of the 2-substituent of the benzimidazole ring led to a series of agonists with subnanomolar binding affinity and moderate-to-high intrinsic activity relative to that of 5-HT. Consistent with our previously described multivalent design approach to this target, subsequent optimization of the linker and secondary binding group regions of the series afforded compound 18 (TD-8954), a potent and selective 5-HT4 receptor agonist in vitro with demonstrated prokinetic activity in multiple species. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.018

文献信息

• Enantioselective Syntheses of Tricyclic Benzimidazoles via Intramolecular Allylic Aminations with Chiral-Bridged Biphenyl Phosphoramidite Ligands
  作者：Xiaoding Jiang、Xiangmeng Chen、Yongsu Li、Hao Liang、Yaqi Zhang、Xiaobo He、Bin Chen、Wesley Ting Kwok Chan、Albert S. C. Chan、Liqin Qiu

  DOI：10.1021/acs.orglett.8b03640

  日期：2019.2.1

  The first iridium-catalyzed enantioselective intramolecular allylic aminations of benzimidazole-tethered allylic carbonates were developed, providing three classes of tricyclic benzimidazoles bearing a tertiary carbon stereogenic center in high yields and excellent enantioselectivities (up to 99% yield, 99% ee). Wide substrate scope, excellent catalytic efficiency and mild conditions rendered this

  开发了首批铱催化的苯并咪唑系留的碳酸烯丙酯的对映选择性分子内烯丙基胺化反应，提供了三类三环苯并咪唑，它们具有叔碳立构中心，具有高收率和优异的对映选择性（高达99％，99％ee）。广泛的底物范围，出色的催化效率和温和条件使该方案特别优越和实用。令人印象深刻的是，具有可调结构的手性桥被证明为手性环境提供了很好的调节空间。在这些转化中，配体的优异催化性能表现出了优于基于双酚和BINOL的对应物的优势。它还强调了手性桥联配体的潜在应用价值。
• 一种苯并咪唑并手性杂环类化合物及其制备 方法和应用
  申请人：中山大学

  公开号：CN109336887B

  公开（公告）日：2021-12-17

  本发明公开了一种苯并咪唑并手性杂环类化合物及其制备方法和应用，结构式为式I、式II或式III，所述化合物是以金属铱化合物和亚磷酰胺配体形成的铱络合物作为催化剂，由烯丙基类底物进行分子内的烯丙基胺化反应，高效率、高对映选择性的合成获得。该方法具有催化反应活性高、反应条件温和、对映选择性好、底物适用范围广、环境友好等优点。初步体外酶抑制活性试验表明，本发明所述化合物具有较好的α‑葡萄糖苷酶抑制活性，可作为α‑葡萄糖苷酶抑制剂，同时也可以作为进一步修饰的药物中间体，具有制备预防或治疗II‑型糖尿病、肥胖症及其并发症药物及其先导化合物的潜在应用价值。