(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 | 786658-80-8

• 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: (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
• CAS: 786658-80-8
• 化学式: C₅₃H₉₁N₇O₉
• 分子量: 970.347
• InChiKey: BBWQHGQWBKLIKF-VGEOQMRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  69.0
• 可旋转键数：
  29.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  191.85
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (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 在 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 28.0h， 生成 (5S,8S,11S,14S,17S,20S)-14-[(1-methoxyindol-3-yl)methyl]-7,13,19,20-tetramethyl-5,17-bis[(2R)-2-methylhexyl]-8,11-bis(2-methylpropyl)-1-oxa-4,7,10,13,16,19-hexazacyclohenicosane-3,6,9,12,15,18-hexone
  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-[[N-[N-[N-[(2S,4R)-2-amino-4-methylheptanoyl]-N-methyl-L-leucinyl]-L-leucinyl]-N¹'-methoxy-N-methyl-L-tryptophanyl]amino]-4-methylheptanoyl]-N-methyl-L-alanine methyl ester 在 锂硼氢 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (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