octyl N-[(1S)-1-benzyl-2-oxo-2-(3-oxopyrrolidin-1-yl)ethyl]carbamate

• 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: octyl N-[(1S)-1-benzyl-2-oxo-2-(3-oxopyrrolidin-1-yl)ethyl]carbamate
• 英文别名: octyl N-[(2S)-1-oxo-1-(3-oxopyrrolidin-1-yl)-3-phenylpropan-2-yl]carbamate
• 化学式: C₂₂H₃₂N₂O₄
• 分子量: 388.507
• InChiKey: KCBKSHBFCLDIAQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester 在 sodium hydroxide 、 TEA 、 二甲基亚砜 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 octyl N-[(1S)-1-benzyl-2-oxo-2-(3-oxopyrrolidin-1-yl)ethyl]carbamate
  参考文献：
  名称：

  Syntheses of new modified Phe-Pro peptides. Use of proline replacements in potential HIV inhibitors

  摘要：

  The syntheses consisting of replacement of proline amino acid by a 3-pyrrolidinone ring in Phe-Pro analogues are described. Preliminary anti-HIV studies demonstrated the potential activity of this new class of compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00006-7

文献信息

• Short and unexpectedly potent 3-pyrrolidinone type inhibitors of HIV-1 replication
  作者：Martin Bouygues、Martial Medou、Jean-Claude Chermann、Michel Camplo、Jean-Louis Kraus

  DOI：10.1016/s0223-5234(98)80045-7

  日期：1998.6

  Based on the specific PhePro proteolytic cleavage of the HIV protease, short pseudo-peptides incorporating a 3-pyrrolidinone ring have been synthesized. Their potencies to inhibit HIV-1 in MT4 cell culture have been evaluated and compared to that of the bioisostere dipeptide BocPhePro. Analogues incorporating an aromatic residue have shown to inhibit HIV-1 infection in MT4 human lymphoid cell with an IC50 ranging from 1 to 10 mu M. Further experiments are in progress to determine their HIV protease inhibition properties. (C) Elsevier, Paris.