2-[2-(2-benzyloxycarbonylamino-3-phenylpropionylamino)-4-methyl-pentanoylamino]-3-(2-oxo-pyrrolidin-3-yl)propionic acid methyl ester

• 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: 2-[2-(2-benzyloxycarbonylamino-3-phenylpropionylamino)-4-methyl-pentanoylamino]-3-(2-oxo-pyrrolidin-3-yl)propionic acid methyl ester
• 英文别名: Cbz-Phe-Leu-Ala((S)-2-oxopyrrolidin-3-yl)-OMe；methyl (2S)-2-[[(2S)-4-methyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]pentanoyl]amino]-3-[(3S)-2-oxopyrrolidin-3-yl]propanoate
• 化学式: C₃₁H₄₀N₄O₇
• 分子量: 580.681
• InChiKey: LYXXJRZRNBBZDL-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-(2-benzyloxycarbonylamino-3-phenylpropionylamino)-4-methyl-pentanoylamino]-3-(2-oxo-pyrrolidin-3-yl)propionic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and bioevaluation of viral 3C and 3C-like protease inhibitors

  摘要：

  A class of tripeptidyl transition state inhibitors containing a P1 glutamine surrogate, a P2 leucine, and a P3 arylalanines, was found to potently inhibit Norwalk virus replication in enzyme and cell based assays. An array of warheads, including aldehyde, a-ketoamide, bisulfite adduct, and a-hydroxyphosphonate transition state mimic, was also investigated. Tripeptidyls 2 and 6 possess antiviral activities against noroviruses, human rhinovirus, severe acute respiratory syndrome coronavirus, and coronavirus 229E, suggesting a broad range of antiviral activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.070
• 作为产物：
  描述：

  methyl (S)-2-amino-3-((S)-2-oxopyrrolidin-3-yl)propanoate hydrochloride 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 2-[2-(2-benzyloxycarbonylamino-3-phenylpropionylamino)-4-methyl-pentanoylamino]-3-(2-oxo-pyrrolidin-3-yl)propionic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and bioevaluation of viral 3C and 3C-like protease inhibitors

  摘要：

  A class of tripeptidyl transition state inhibitors containing a P1 glutamine surrogate, a P2 leucine, and a P3 arylalanines, was found to potently inhibit Norwalk virus replication in enzyme and cell based assays. An array of warheads, including aldehyde, a-ketoamide, bisulfite adduct, and a-hydroxyphosphonate transition state mimic, was also investigated. Tripeptidyls 2 and 6 possess antiviral activities against noroviruses, human rhinovirus, severe acute respiratory syndrome coronavirus, and coronavirus 229E, suggesting a broad range of antiviral activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.070

文献信息

• Design, synthesis, and bioevaluation of viral 3C and 3C-like protease inhibitors
  作者：Allan M. Prior、Yunjeong Kim、Sahani Weerasekara、Meghan Moroze、Kevin R. Alliston、Roxanne Adeline Z. Uy、William C. Groutas、Kyeong-Ok Chang、Duy H. Hua

  DOI：10.1016/j.bmcl.2013.09.070

  日期：2013.12

  A class of tripeptidyl transition state inhibitors containing a P1 glutamine surrogate, a P2 leucine, and a P3 arylalanines, was found to potently inhibit Norwalk virus replication in enzyme and cell based assays. An array of warheads, including aldehyde, a-ketoamide, bisulfite adduct, and a-hydroxyphosphonate transition state mimic, was also investigated. Tripeptidyls 2 and 6 possess antiviral activities against noroviruses, human rhinovirus, severe acute respiratory syndrome coronavirus, and coronavirus 229E, suggesting a broad range of antiviral activities. (C) 2013 Elsevier Ltd. All rights reserved.