(2-{(S)-1-[(E)-(1S,2R)-1-(2-Hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester | 326473-66-9

• 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: (2-{(S)-1-[(E)-(1S,2R)-1-(2-Hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester
• CAS: 326473-66-9
• 化学式: C₂₇H₄₃N₃O₅
• 分子量: 489.656
• InChiKey: BXMFADKYWWFURS-QIUANZKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  116.76
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-{(S)-1-[(E)-(1S,2R)-1-(2-Hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester 在 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.67h， 生成 (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-Amino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis of Amide Analogs of Arenastatin A

  摘要：

  In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00766-3
• 作为产物：
  描述：

  (E)-(1S,2R)-1-(2-Methoxymethoxy-ethyl)-2-methyl-4-phenyl-but-3-enylamine 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2-{(S)-1-[(E)-(1S,2R)-1-(2-Hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Amide Analogs of Arenastatin A

  摘要：

  In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00766-3