(S)-2-Amino-4-methyl-pentanoic acid [(1R,2S)-2-(3-chloro-phenyl)-cyclohexyl]-amide | 882297-71-4

• 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: (S)-2-Amino-4-methyl-pentanoic acid [(1R,2S)-2-(3-chloro-phenyl)-cyclohexyl]-amide
• 英文别名: (2S)-2-amino-N-[(1R,2S)-2-(3-chlorophenyl)cyclohexyl]-4-methylpentanamide
• CAS: 882297-71-4
• 化学式: C₁₈H₂₇ClN₂O
• 分子量: 322.878
• InChiKey: LQCFVROOYZLVAD-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-4-methyl-pentanoic acid [(1R,2S)-2-(3-chloro-phenyl)-cyclohexyl]-amide 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.08h， 生成 (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：

  1-chloro-3-((1S,2R)-2-nitrocyclohexyl)benzene 在 盐酸 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-2-Amino-4-methyl-pentanoic acid [(1R,2S)-2-(3-chloro-phenyl)-cyclohexyl]-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