Tert-butyl 2-chloro-4-methylbenzimidazole-1-carboxylate | 256519-07-0

• 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: Tert-butyl 2-chloro-4-methylbenzimidazole-1-carboxylate
• CAS: 256519-07-0
• 化学式: C₁₃H₁₅ClN₂O₂
• 分子量: 266.727
• InChiKey: LINVHEWWYHXHNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  螺[异苯并呋喃-1(3H),4'-哌啶]-3-酮盐酸盐 、 Tert-butyl 2-chloro-4-methylbenzimidazole-1-carboxylate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

  摘要：

  Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.018
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-氯-4-甲基-(9ci)-1H-苯并咪唑 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 生成 Tert-butyl 2-chloro-4-methylbenzimidazole-1-carboxylate
  参考文献：
  名称：

  Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

  摘要：

  Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.018

文献信息

• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• [EN] CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY<br/>[FR] COMPOSES HETEROCYCLIQUES A EFFICACITE ACCRUE SE FIXANT SUR LES RECEPTEURS DE LA CHIMIOKINE
  申请人：ANORMED INC

  公开号：WO2003055876A1

  公开（公告）日：2003-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  本发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中的两个首选为苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N并可选择性地含有其他环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并对人免疫缺陷病毒（HIV）感染靶细胞表现出保护作用。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY
  申请人：BRIDGER Gary

  公开号：US20080167341A1

  公开（公告）日：2008-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  该发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中有两个是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可以含有额外的环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护效果。
• Chemokine Receptor Binding Heterocyclic Compounds With Enhanced Efficacy
  申请人：Genzyme Corporation

  公开号：US20150038509A1

  公开（公告）日：2015-02-05

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  该发明涉及杂环化合物，其由一个核心氮原子和三个下垂基团组成，其中三个下垂基团中的两个优选为苯并咪唑甲基和四氢喹啉基，第三个下垂基团含有N，并且可以包含其他环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并且对人类免疫缺陷病毒（HIV）感染目标细胞具有保护作用。
• EP1465889A4
  申请人：——

  公开号：EP1465889A4

  公开（公告）日：2008-05-14