2-({2-[2-[(2-{2-[(2-tert-butoxycarbonylamino-4-methyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-4-methyl-pentanoyl)-methyl-amino]-3-(1-methoxy-1H-indol-3-yl)-propionylamino]-4-methyl-octanoyl}-methyl-amino)-propionic acid methyl ester | 786658-78-4

• 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-[(2-{2-[(2-tert-butoxycarbonylamino-4-methyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-4-methyl-pentanoyl)-methyl-amino]-3-(1-methoxy-1H-indol-3-yl)-propionylamino]-4-methyl-octanoyl}-methyl-amino)-propionic acid methyl ester
• CAS: 786658-78-4
• 化学式: C₅₄H₉₁N₇O₁₀
• 分子量: 998.357
• InChiKey: IIBVSYFUEAPOQT-VGEOQMRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  71.0
• 可旋转键数：
  29.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  197.92
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-({2-[2-[(2-{2-[(2-tert-butoxycarbonylamino-4-methyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-4-methyl-pentanoyl)-methyl-amino]-3-(1-methoxy-1H-indol-3-yl)-propionylamino]-4-methyl-octanoyl}-methyl-amino)-propionic acid methyl ester 在 锂硼氢 作用下， 以 甲醇 为溶剂， 以73%的产率得到(1-{[1-(1-{[1-{1-[(2-hydroxy-1-methyl-ethyl)-methyl-carbamoyl]-3-methyl-heptylcarbamoyl}-2-(1-methoxy-1H-indol-3-yl)-ethyl]-methyl-carbamoyl}-3-methyl-butylcarbamoyl)-3-methyl-butyl]-methyl-carbamoyl}-3-methyl-heptyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of ether analogues derived from HUN-7293 and evaluation as inhibitors of VCAM-1 expression

  摘要：

  The cyclic depsipeptide HUN-7293 (1) and its D-lactate analogue 2 are highly potent inhibitors of inducible cell adhesion molecule expression. We report the synthesis of ether analogues varying in stereochemistry and side chain at the former hydroxyl acid position by employing a 'cut and paste chemistry' methodology starting from 1. As an additional fruit of this synthetic effort, a cyclodepsipeptide featuring a tertiary amine instead of a tertiary amide between PrLEU and MALA was obtained. Results on the inhibitory profile of these compounds in assays of VCAM-1 and ICAM-1 protein expression are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.012
• 作为产物：
  描述：

  N-<(2S,4R)-2-<amino>-4-methylheptanoyl>-N-methyl-L-leucinyl>-L-leucinyl>-N^1'-methoxy-N-methyl-L-tryptophanyl>amino>-4-methylheptanoyl>-N-methyl-L-alanine methyl ester 在 N-甲基吗啉 、 乙基硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 2-({2-[2-[(2-{2-[(2-tert-butoxycarbonylamino-4-methyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-4-methyl-pentanoyl)-methyl-amino]-3-(1-methoxy-1H-indol-3-yl)-propionylamino]-4-methyl-octanoyl}-methyl-amino)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of ether analogues derived from HUN-7293 and evaluation as inhibitors of VCAM-1 expression

  摘要：

  The cyclic depsipeptide HUN-7293 (1) and its D-lactate analogue 2 are highly potent inhibitors of inducible cell adhesion molecule expression. We report the synthesis of ether analogues varying in stereochemistry and side chain at the former hydroxyl acid position by employing a 'cut and paste chemistry' methodology starting from 1. As an additional fruit of this synthetic effort, a cyclodepsipeptide featuring a tertiary amine instead of a tertiary amide between PrLEU and MALA was obtained. Results on the inhibitory profile of these compounds in assays of VCAM-1 and ICAM-1 protein expression are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.012