2-(4-Bromomethyl-benzoyl)-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide | 911141-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(4-Bromomethyl-benzoyl)-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide
• CAS: 911141-89-4
• 化学式: C₃₂H₄₀BrClN₂O₃
• 分子量: 616.038
• InChiKey: LVBNLENLCBCFLN-WZDMDNGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-Bromomethyl-benzoyl)-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide 、 2-氨基噻唑 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 (1S,2S)-2-[4-(Thiazol-2-ylaminomethyl)-benzoyl]-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide 、 (1R,2R)-2-[4-(Thiazol-2-ylaminomethyl)-benzoyl]-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide
  参考文献：
  名称：

  CDK2/cyclinA inhibitors: Targeting the cyclinA recruitment site with small molecules derived from peptide leads

  摘要：

  The syntheses of potent small molecule inhibitors of the CDK2/cyclinA recruitment site are described. Structure-activity trends of nanomolar octapeptides were examined through amino-acid substitution and truncation of the sequence resulting in the identification of a smaller, albeit significantly less potent, tetrapeptide lead. These losses in affinity were recovered by side-chain optimization and by rigidification of the peptide backbone using a combination of solid-phase parallel synthesis and structure-based design. Finally, two guanidine functionalities were replaced to improve drug-like properties, resulting in neutral small molecules equal in activity to that of the peptide lead. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.004
• 作为产物：
  描述：

  (1R,2S)-2-(3-Chloro-phenyl)-cyclohexylamine 在 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-Bromomethyl-benzoyl)-cyclopentanecarboxylic acid {(S)-1-[(1R,2S)-2-(3-chloro-phenyl)-cyclohexylcarbamoyl]-3-methyl-butyl}-amide
  参考文献：
  名称：

  CDK2/cyclinA inhibitors: Targeting the cyclinA recruitment site with small molecules derived from peptide leads

  摘要：

  The syntheses of potent small molecule inhibitors of the CDK2/cyclinA recruitment site are described. Structure-activity trends of nanomolar octapeptides were examined through amino-acid substitution and truncation of the sequence resulting in the identification of a smaller, albeit significantly less potent, tetrapeptide lead. These losses in affinity were recovered by side-chain optimization and by rigidification of the peptide backbone using a combination of solid-phase parallel synthesis and structure-based design. Finally, two guanidine functionalities were replaced to improve drug-like properties, resulting in neutral small molecules equal in activity to that of the peptide lead. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.004