[(S)-1-(4-Chloro-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester | 1027424-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [(S)-1-(4-Chloro-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S)-1-(4-chlorophenyl)-2-oxopyrrolidin-3-yl]carbamate
• CAS: 1027424-72-1
• 化学式: C₁₅H₁₉ClN₂O₃
• 分子量: 310.78
• InChiKey: GTROVJFXJXSQRJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(S)-1-(4-Chloro-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 生成 (S)-3-Amino-1-(4-chloro-phenyl)-pyrrolidin-2-one; hydrochloride
  参考文献：
  名称：

  Design and Biological Activity of (S)-4-(5-{[1-(3-Chlorobenzyl)-2- oxopyrrolidin-3-ylamino]methyl}imidazol-1-ylmethyl)benzonitrile, a 3-Aminopyrrolidinone Farnesyltransferase Inhibitor with Excellent Cell Potency

  摘要：

  The synthesis, structure-activity relationships, and biological properties of a novel series of imidazole-containing inhibitors of farnesyltransferase are described. Starting from a 3-amino-pyrrolidinone core, a systematic series of modifications provided 5h, a non-thiol, non-peptide farnesyltransferase inhibitor with excellent bioavailability in dogs. Compound 5h was found to have an unusually favorable ratio of cell potency to intrinsic potency, compared with other known FTIs. It exhibited excellent potency against a range of tumor cell lines in vitro and showed full efficacy in the K-rasB transgenic mouse model.

  DOI：

  10.1021/jm010156p
• 作为产物：
  描述：

  [(S)-3-tert-Butoxycarbonylamino-3-(4-chloro-phenylcarbamoyl)-propyl]-dimethyl-sulfonium; iodide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(S)-1-(4-Chloro-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and Biological Activity of (S)-4-(5-{[1-(3-Chlorobenzyl)-2- oxopyrrolidin-3-ylamino]methyl}imidazol-1-ylmethyl)benzonitrile, a 3-Aminopyrrolidinone Farnesyltransferase Inhibitor with Excellent Cell Potency

  摘要：

  The synthesis, structure-activity relationships, and biological properties of a novel series of imidazole-containing inhibitors of farnesyltransferase are described. Starting from a 3-amino-pyrrolidinone core, a systematic series of modifications provided 5h, a non-thiol, non-peptide farnesyltransferase inhibitor with excellent bioavailability in dogs. Compound 5h was found to have an unusually favorable ratio of cell potency to intrinsic potency, compared with other known FTIs. It exhibited excellent potency against a range of tumor cell lines in vitro and showed full efficacy in the K-rasB transgenic mouse model.

  DOI：

  10.1021/jm010156p