(3S,4S)-N-[(2S)-1-(benzylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-hydroxy-4-[[(2R)-2-[4-(4-hydroxyphenyl)butanoylamino]-5-[[N'-(3-methylbut-2-enyl)carbamimidoyl]amino]pentanoyl]amino]-5-phenylpentanamide | 1299326-12-7

• 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: (3S,4S)-N-[(2S)-1-(benzylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-hydroxy-4-[[(2R)-2-[4-(4-hydroxyphenyl)butanoylamino]-5-[[N'-(3-methylbut-2-enyl)carbamimidoyl]amino]pentanoyl]amino]-5-phenylpentanamide
• CAS: 1299326-12-7
• 化学式: C₄₈H₆₁N₇O₇
• 分子量: 848.055
• InChiKey: ZYZKOHKCJHAFRZ-NCZZEDDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  62
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  228
• 氢给体数：
  9
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4S)-N-[(2S)-1-(benzylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-hydroxy-4-[[(2R)-2-[4-(4-hydroxyphenyl)butanoylamino]-5-[[N'-(3-methylbut-2-enyl)carbamimidoyl]amino]pentanoyl]amino]-5-phenylpentanamide 、 三甲基硅烷化重氮甲烷 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到
  参考文献：
  名称：

  Stictamides A−C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits

  摘要：

  An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.

  DOI：

  10.1021/jo200241h
• 作为产物：
  描述：

  stictamide A 、 苄胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以83%的产率得到(3S,4S)-N-[(2S)-1-(benzylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-hydroxy-4-[[(2R)-2-[4-(4-hydroxyphenyl)butanoylamino]-5-[[N'-(3-methylbut-2-enyl)carbamimidoyl]amino]pentanoyl]amino]-5-phenylpentanamide
  参考文献：
  名称：

  Stictamides A−C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits

  摘要：

  An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.

  DOI：

  10.1021/jo200241h