1-[(tert-butoxycarbonyl)-L-tyrosyl]-3-pyrrolidinone | 216392-38-0

• 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: 1-[(tert-butoxycarbonyl)-L-tyrosyl]-3-pyrrolidinone
• 英文别名: tert-butyl N-[(2S)-3-(4-hydroxyphenyl)-1-oxo-1-(3-oxopyrrolidin-1-yl)propan-2-yl]carbamate
• CAS: 216392-38-0
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: DQLDSUYPUGAJDR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-苯基硫代苯基砜 、 1-[(tert-butoxycarbonyl)-L-tyrosyl]-3-pyrrolidinone 在 仲丁基锂 作用下， 以 甲苯 为溶剂， 生成 [(S)-1-(4-Hydroxy-benzyl)-2-oxo-2-((R)-3-oxo-2-phenylsulfanyl-pyrrolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester 、 [(S)-1-(4-Hydroxy-benzyl)-2-oxo-2-((S)-3-oxo-2-phenylsulfanyl-pyrrolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  use of proline bioisosteres in potential HIV protease inhibitors: phenylalanine-2-thiophenoxy-3-pyrrolidinone: synthesis and anti-HIV evaluation

  摘要：

  The synthesis of new phenylalanine-2-thiophenoxy-3-pyrrolidinones is described. Anti-HIV recombinant protease assays and HIV infected cell culture assays (observation of syncytia) demonstrated the potent anti-HIV activity of this new class of pseudopeptides. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00393-0
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 1,4-环己二烯 、 碳酸氢钠 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 potassium bromide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-[(tert-butoxycarbonyl)-L-tyrosyl]-3-pyrrolidinone
  参考文献：
  名称：

  Short and unexpectedly potent 3-pyrrolidinone type inhibitors of HIV-1 replication

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(98)80045-7

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.
• use of proline bioisosteres in potential HIV protease inhibitors: phenylalanine-2-thiophenoxy-3-pyrrolidinone: synthesis and anti-HIV evaluation
  作者：J.L Kraus、M Bouygues、J Courcambeck、J.C Chermann

  DOI：10.1016/s0960-894x(00)00393-0

  日期：2000.9

  The synthesis of new phenylalanine-2-thiophenoxy-3-pyrrolidinones is described. Anti-HIV recombinant protease assays and HIV infected cell culture assays (observation of syncytia) demonstrated the potent anti-HIV activity of this new class of pseudopeptides. (C) 2000 Published by Elsevier Science Ltd.