(S)-3-((S)-2-(benzyloxycarbonylamino)-3-methylbutanamido)-5-(phenylsulfonyl)pent-4-enoic acid | 1246261-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-3-((S)-2-(benzyloxycarbonylamino)-3-methylbutanamido)-5-(phenylsulfonyl)pent-4-enoic acid
• 英文别名: (E,3S)-5-(benzenesulfonyl)-3-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pent-4-enoic acid
• CAS: 1246261-40-4
• 化学式: C₂₄H₂₈N₂O₇S
• 分子量: 488.562
• InChiKey: STFWSJDDUOPNEW-SJPVHQJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl (S)-3-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-5-(phenylsulfonyl)pent-4-enoate 在 三氟乙酸 作用下， 反应 1.0h， 以99%的产率得到(S)-3-((S)-2-(benzyloxycarbonylamino)-3-methylbutanamido)-5-(phenylsulfonyl)pent-4-enoic acid
  参考文献：
  名称：

  Synthesis and evaluation of vinyl sulfones as caspase-3 inhibitors. A structure–activity study

  摘要：

  The first structure activity relationship study of vinyl sulfones as caspase-3 inhibitors is reported. A series of 12 vinyl sulfones was synthesized and evaluated for two downstream caspases (caspases-3 and -7). Dipeptidyl derivatives were significantly superior to their counterparts containing only Asp at P(1), as caspase-3 inhibitors. Fmoc-Val-Asp-trans-CH=CH-SO(2)Me was the most potent inhibitor of caspase-3 in the series, with a IC(50) of 29 mu M and a second-order rate constant of inactivation, k(inact)/(K)i, of 1.5 M(-1) s(-1) Computational studies suggest that the second amino acid occupies position S(3) of the enzyme. In addition, Fmoc-Val-Asp-trans-CH=CH-SO(2)Ph was inactive for caspase-7 for the tested concentrations. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.039

文献信息

• Synthesis and evaluation of vinyl sulfones as caspase-3 inhibitors. A structure–activity study
  作者：Ana S. Newton、Paulo M.C. Glória、Lídia M. Gonçalves、Daniel J.V.A. dos Santos、Rui Moreira、Rita C. Guedes、Maria M.M. Santos

  DOI：10.1016/j.ejmech.2010.05.039

  日期：2010.9

  The first structure activity relationship study of vinyl sulfones as caspase-3 inhibitors is reported. A series of 12 vinyl sulfones was synthesized and evaluated for two downstream caspases (caspases-3 and -7). Dipeptidyl derivatives were significantly superior to their counterparts containing only Asp at P(1), as caspase-3 inhibitors. Fmoc-Val-Asp-trans-CH=CH-SO(2)Me was the most potent inhibitor of caspase-3 in the series, with a IC(50) of 29 mu M and a second-order rate constant of inactivation, k(inact)/(K)i, of 1.5 M(-1) s(-1) Computational studies suggest that the second amino acid occupies position S(3) of the enzyme. In addition, Fmoc-Val-Asp-trans-CH=CH-SO(2)Ph was inactive for caspase-7 for the tested concentrations. (C) 2010 Elsevier Masson SAS. All rights reserved.