3-(9-Oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzoic acid | 433726-34-2

• 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-(9-Oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzoic acid
• CAS: 433726-34-2
• 化学式: C₁₇H₁₃N₃O₃
• 分子量: 307.309
• InChiKey: HBCBLKDIMOYKQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基-1,3-丙二胺 、 3-(9-Oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzoic acid 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 生成 N-[3-(dimethylamino)propyl]-N-methyl-3-(9-oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzamide
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. part 4: Biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries

  摘要：

  A class of poly(ADP-ribose) polymerase (PARP-1) inhibitors, the imidazobenzodiazepines, are presented in this text. Several derivatives were designed and synthesized with ionizable groups (i.e., tertiary amines) in order to promote the desired pharmaceutical characteristics for administration in ischemic injury. Within this series, several compounds have excellent in vitro potency and our computational models accurately justify the structure-activity relationships (SARs) and highlight essential hydrogen bonding residues and hydrophobic pockets within the catalytic domain of PARP-1. Administration of these compounds (5q, 17a and 17e) in the mouse model of streptozotocin-induced diabetes results in maintainance of glucose levels. Furthermore, one such inhibitor (5g, IC50 = 26 nM) demonstrated significant reduction of infarct volume in the rat model of permanent focal cerebral ischemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00333-x
• 作为产物：
  描述：

  9-硝基-1,2,3,4-四氢-5H-1,4-苯并二氮杂卓-5-酮 在 palladium on activated charcoal 镍 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 3-(9-Oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzoic acid
  参考文献：
  名称：

  Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. part 4: Biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries

  摘要：

  A class of poly(ADP-ribose) polymerase (PARP-1) inhibitors, the imidazobenzodiazepines, are presented in this text. Several derivatives were designed and synthesized with ionizable groups (i.e., tertiary amines) in order to promote the desired pharmaceutical characteristics for administration in ischemic injury. Within this series, several compounds have excellent in vitro potency and our computational models accurately justify the structure-activity relationships (SARs) and highlight essential hydrogen bonding residues and hydrophobic pockets within the catalytic domain of PARP-1. Administration of these compounds (5q, 17a and 17e) in the mouse model of streptozotocin-induced diabetes results in maintainance of glucose levels. Furthermore, one such inhibitor (5g, IC50 = 26 nM) demonstrated significant reduction of infarct volume in the rat model of permanent focal cerebral ischemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00333-x

文献信息

• US7235557B2
  申请人：——

  公开号：US7235557B2

  公开（公告）日：2007-06-26
• US7915280B2
  申请人：——

  公开号：US7915280B2

  公开（公告）日：2011-03-29
• USRE41150E1
  申请人：——

  公开号：USRE41150E1

  公开（公告）日：2010-02-23