(S)-5-(4,5-Diphenyl-oxazol-2-ylsulfanyl)-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid | 862699-30-7

• 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)-5-(4,5-Diphenyl-oxazol-2-ylsulfanyl)-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid
• 英文别名: (3S)-5-[(4,5-Diphenyl-2-oxazolyl)thio]-3-[[(2S)-3-methyl-2-[[2-(1-naphthalenyloxy)acetyl]amino]-1-oxobutyl]amino]-4-oxopentanoic acid；(3S)-5-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]-3-[[(2S)-3-methyl-2-[(2-naphthalen-1-yloxyacetyl)amino]butanoyl]amino]-4-oxopentanoic acid
• CAS: 862699-30-7
• 化学式: C₃₇H₃₅N₃O₇S
• 分子量: 665.767
• InChiKey: PVVPZVAFPKLLFZ-UVMMSNCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  173
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  L-valinyl-L-aspartyl-β-(tert-butyl ester) methyl ester 在 N-甲基吗啉 、 potassium fluoride 、 lithium hydroxide 、 氢溴酸 、 1-羟基苯并三唑 、 苯甲醚 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成 (S)-5-(4,5-Diphenyl-oxazol-2-ylsulfanyl)-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid
  参考文献：
  名称：

  Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads

  摘要：

  Various heterocyclic hetero-methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A study of their structure-activity relationship (SAR) related to caspase-1, -3, -6, and -8 is reported. Their efficacy in a cellular model of cell death is also discussed. Potent broad-spectrum caspase inhibitors have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.036

文献信息

• Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads
  作者：Brett R. Ullman、Teresa Aja、Ning Chen、Jose-Luis Diaz、Xin Gu、Julia Herrmann、Vincent J. Kalish、Donald S. Karanewsky、Lalitha Kodandapani、Joseph J. Krebs、Steven D. Linton、Steven P. Meduna、Kip Nalley、Edward D. Robinson、Silvio P. Roggo、Robert O. Sayers、Albert Schmitz、Robert J. Ternansky、Kevin J. Tomaselli、Joe C. Wu

  DOI：10.1016/j.bmcl.2005.05.036

  日期：2005.8

  Various heterocyclic hetero-methyl ketones of the 1-naphthyloxyacetyl-Val-Asp backbone have been prepared. A study of their structure-activity relationship (SAR) related to caspase-1, -3, -6, and -8 is reported. Their efficacy in a cellular model of cell death is also discussed. Potent broad-spectrum caspase inhibitors have been identified. (c) 2005 Elsevier Ltd. All rights reserved.