3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazole-5-carboxylic acid | 950668-25-4

• 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-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazole-5-carboxylic acid
• CAS: 950668-25-4
• 化学式: C₂₄H₂₈N₄O₃
• 分子量: 420.511
• InChiKey: BBVMQUMBGUBCTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazole-5-carboxylic acid 在 lithium aluminium tetrahydride 、 TEA 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazol-5-yl]acetonitrile
  参考文献：
  名称：

  Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity

  摘要：

  Extensive SAR studies and optimization of ADME properties of benzimidazol-2-one derivatives led to the identification of BMS-433771 (3) as an orally active RSV fusion inhibitor. In order to extend the structure-activity relationships for this compound series, substitution of the benzimidazole ring was examined with a view to establishing additional productive interactions between the inhibitor and functionality present in the proposed binding pocket. Amongst the compounds synthesized, the 5-aminomethyl analogue 10aa demonstrated potent antiviral activity towards wild-type RSV and retained excellent inhibitory activity towards a virus that had been developed to express resistance to BMS-433771 (3), data consistent with an additional productive interaction between the inhibitor and the fusion protein target. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.102
• 作为产物：
  描述：

  异戊胺 在 palladium on activated charcoal sodium hydroxide 、 氯化亚砜 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity

  摘要：

  Extensive SAR studies and optimization of ADME properties of benzimidazol-2-one derivatives led to the identification of BMS-433771 (3) as an orally active RSV fusion inhibitor. In order to extend the structure-activity relationships for this compound series, substitution of the benzimidazole ring was examined with a view to establishing additional productive interactions between the inhibitor and functionality present in the proposed binding pocket. Amongst the compounds synthesized, the 5-aminomethyl analogue 10aa demonstrated potent antiviral activity towards wild-type RSV and retained excellent inhibitory activity towards a virus that had been developed to express resistance to BMS-433771 (3), data consistent with an additional productive interaction between the inhibitor and the fusion protein target. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.102

文献信息

• Piperidyindoles as serotonin receptor ligands
  申请人：——

  公开号：US20030225068A1

  公开（公告）日：2003-12-04

  A pharmaceutical compound of the formula (I) in which R 1 and R 2 are each hydrogen or C 1-6 alkyl, R 3 is —SR 10 , —SOR 10 , —SO 2 R 10 , —COR 10 , —CH 2 OH or —CONHR 11 , where R 10 is C 1-6 alkyl and R 11 is hydrogen or C 1-6 alkyl, R 4 , R 5 , R 6 and R 7 are each hydrogen or C 1-6 alkyl, provided that at least one of R 4 , R 5 , R 6 and R 7 is C 1-6 alkyl, R 8 and R 9 are each hydrogen, halo, C 1-6 alkyl or cyano, n is 0 or 1 and m is 2 or 3, x is a (a) or (b), and y is (c) or (d), wherein R 12 and R 13 are each hydrogen, C 1- alkyl, cyclopropyl or cyclopropyl-C 1-6 alkyl; and salts thereof. 1

  化学式（I）中的一种药物化合物，其中R1和R2分别为氢或C1-6烷基，R3为—SR10，—SOR10，—SO2R10，—COR10，—CH2OH或—CONHR11，其中R10为C1-6烷基，R11为氢或C1-6烷基，R4、R5、R6和R7分别为氢或C1-6烷基，但至少其中之一为C1-6烷基，R8和R9分别为氢、卤素、C1-6烷基或氰基，n为0或1，m为2或3，x为（a）或（b），y为（c）或（d），其中R12和R13分别为氢、C1-烷基、环丙基或环丙基-C1-6烷基；及其盐。
• Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
  申请人：——

  公开号：US20030207868A1

  公开（公告）日：2003-11-06

  The present invention concerns antiviral compounds, their methods of preparation and their compositions, and use in the treatment of viral infections. More particularly, the invention provides heterocyclic substituted 2-methylbenzimidazole derivatives for the treatment of respiratory syncytial virus infection.

  本发明涉及抗病毒化合物，其制备方法及其组合物，以及在治疗病毒感染中的应用。更具体地，该发明提供了用于治疗呼吸道合胞病毒感染的杂环取代2-甲基苯并咪唑衍生物。
• SUBSTITUTED 2-METHYL-BENZIMIDAZOLE RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1461035A2

  公开（公告）日：2004-09-29
• EP1461035A4
  申请人：——

  公开号：EP1461035A4

  公开（公告）日：2005-04-06
• US6844338B2
  申请人：——

  公开号：US6844338B2

  公开（公告）日：2005-01-18