(S)-2-Amino-3-methyl-pentanoic acid ((1S,2R,3S)-2,3-dihydroxy-5-methyl-1-naphthalen-1-ylmethyl-hexyl)-amide | 1054628-09-9

• 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: (S)-2-Amino-3-methyl-pentanoic acid ((1S,2R,3S)-2,3-dihydroxy-5-methyl-1-naphthalen-1-ylmethyl-hexyl)-amide
• 英文别名: (2S)-2-amino-N-[(2S,3R,4S)-3,4-dihydroxy-6-methyl-1-naphthalen-1-ylheptan-2-yl]-3-methylpentanamide
• CAS: 1054628-09-9
• 化学式: C₂₄H₃₆N₂O₃
• 分子量: 400.561
• InChiKey: UBHIQUQIUYCXPJ-RVFXHGKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  95.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylpropoxycarbonyl (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 、 (S)-2-Amino-3-methyl-pentanoic acid ((1S,2R,3S)-2,3-dihydroxy-5-methyl-1-naphthalen-1-ylmethyl-hexyl)-amide 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 {(S)-1-[(S)-1-((1S,2R,3S)-2,3-Dihydroxy-5-methyl-1-naphthalen-1-ylmethyl-hexylcarbamoyl)-2-methyl-butylcarbamoyl]-2-methyl-butyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung

  摘要：

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.

  DOI：

  10.1021/jm00056a007
• 作为产物：
  描述：

  N-Boc-isoleucine 在 N-甲基吗啉 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 (S)-2-Amino-3-methyl-pentanoic acid ((1S,2R,3S)-2,3-dihydroxy-5-methyl-1-naphthalen-1-ylmethyl-hexyl)-amide
  参考文献：
  名称：

  Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung

  摘要：

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.

  DOI：

  10.1021/jm00056a007

文献信息

• Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung
  作者：Kazumi Shiosaki、Andrew S. Tasker、Gerard M. Sullivan、Bryan K. Sorensen、Thomas W. von Geldern、Jinshyun R. Wu-Wong、Carol A. Marselle、Terry J. Opgenorth

  DOI：10.1021/jm00056a007

  日期：1993.2

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.