(S)-3-(tert-butoxycarbonylamino)-2-oxo-1-phenylpyrrolidine | 175873-05-9

• 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)-3-(tert-butoxycarbonylamino)-2-oxo-1-phenylpyrrolidine
• 英文别名: N-phenyl-3(S)-[[(1,1-dimethylethoxy)carbonyl]amino]pyrrolidin-2-one；tert-butyl N-[(3S)-2-oxo-1-phenylpyrrolidin-3-yl]carbamate
• CAS: 175873-05-9
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: IULGBGUUYULUHE-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 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)-3-(tert-butoxycarbonylamino)-2-oxo-1-phenylpyrrolidine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以99%的产率得到(S)-3-amino-2-oxo-1-phenylpyrrolidine 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)-2-(tert-butoxycarbonylamino)-4-(dimethylsulfonium)-N-phenylbutyramide iodide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到(S)-3-(tert-butoxycarbonylamino)-2-oxo-1-phenylpyrrolidine
  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

文献信息

• PROCESS FOR THE PREPARATION OF AMIDINO PHENYL PYRROLIDINE $g(b)-ALANINE UREA ANALOGS
  申请人：G.D. SEARLE & CO.

  公开号：EP0796245A1

  公开（公告）日：1997-09-24
• PROCESS FOR THE PREPARATION OF AMIDINO PHENYL PYRROLIDINE BETA-ALANINE UREA ANALOGS
  申请人：G.D. SEARLE & CO.

  公开号：EP0796245B1

  公开（公告）日：2000-07-26
• US5484946A
  申请人：——

  公开号：US5484946A

  公开（公告）日：1996-01-16
• US5576447A
  申请人：——

  公开号：US5576447A

  公开（公告）日：1996-11-19
• US5610296A
  申请人：——

  公开号：US5610296A

  公开（公告）日：1997-03-11