Benzyloxycarbonyl-Leu-His-OMe | 2592-22-5

• 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: Benzyloxycarbonyl-Leu-His-OMe
• 英文别名: N^α-(N-benzyloxycarbonyl-leucyl)-histidine methyl ester；BOC-L-Leucyl-L-Histidinmethylester；Cbz-Leu-His-OMe；methyl (2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propanoate
• CAS: 2592-22-5
• 化学式: C₂₁H₂₈N₄O₅
• 分子量: 416.477
• InChiKey: IYXGUMUVBVYSQY-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzyloxycarbonyl-Leu-His-OMe 在 palladium on activated charcoal 氢气 作用下， 生成 环(组氨酰-亮氨酰)
  参考文献：
  名称：

  Mori, Atsunori; Ikeda, Yoshitaka; Kinoshita, Koichi, Chemistry Letters, 1989, p. 2119 - 2122

  摘要：

  DOI：
• 作为产物：
  描述：

  L-组氨酸 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Benzyloxycarbonyl-Leu-His-OMe
  参考文献：
  名称：

  Vlasov, G. P.; Glushenkova, V. R.; Glinskaya, I. V., Journal of general chemistry of the USSR, 1987, vol. 57, p. 1895 - 1901

  摘要：

  DOI：

文献信息

• Mori, Atsunori; Ikeda, Yoshitaka; Kinoshita, Koichi, Chemistry Letters, 1989, p. 2119 - 2122
  作者：Mori, Atsunori、Ikeda, Yoshitaka、Kinoshita, Koichi、Inoue, Shohei

  DOI：——

  日期：——
• Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies
  作者：Peter S. Dragovich、Stephen E. Webber、Robert E. Babine、Shella A. Fuhrman、Amy K. Patick、David A. Matthews、Siegfried H. Reich、Joseph T. Marakovits、Thomas J. Prins、Ru Zhou、Jayashree Tikhe、Ethel S. Littlefield、Ted M. Bleckman、Michael B. Wallace、Thomas L. Little、Clifford E. Ford、James W. Meador、Rose Ann Ferre、Edward L. Brown、Susan L. Binford、Dorothy M. DeLisle、Stephen T. Worland

  DOI：10.1021/jm9800696

  日期：1998.7.1

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.
• MORI, ATSUNORI;IKEDA, YOSHITAKA;KINOSHITA, KOICHI;INOUE, SHOHEI, CHEM. LETT.,(1989) N2, C. 2119-2122
  作者：MORI, ATSUNORI、IKEDA, YOSHITAKA、KINOSHITA, KOICHI、INOUE, SHOHEI

  DOI：——

  日期：——
• Vlasov, G. P.; Glushenkova, V. R.; Glinskaya, I. V., Journal of general chemistry of the USSR, 1987, vol. 57, p. 1895 - 1901
  作者：Vlasov, G. P.、Glushenkova, V. R.、Glinskaya, I. V.、Nadezhina, L. B.、Komogorova, T. A.、Ditkovskaya, I. B.

  DOI：——

  日期：——
• Arena, Giuseppe; Impellizzeri, Giuseppe; Maccarrone, Giuseppe, Journal of the Chemical Society. Perkin transactions II, 1992, # 3, p. 371 - 376
  作者：Arena, Giuseppe、Impellizzeri, Giuseppe、Maccarrone, Giuseppe、Pappalardo, Giuseppe、Sciotto, Domenico、Rizzarelli, Enrico

  DOI：——

  日期：——