(3S,10R,16S)-16-((1S)-1-{(2R,3R)-3-[4-(chloromethyl)phenyl]oxiranyl}ethyl)-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone | 916452-58-9

• 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: (3S,10R,16S)-16-((1S)-1-{(2R,3R)-3-[4-(chloromethyl)phenyl]oxiranyl}ethyl)-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone
• CAS: 916452-58-9
• 化学式: C₃₅H₄₄ClN₃O₇
• 分子量: 654.203
• InChiKey: RUIWLBCQHDVEJX-BYBOGOSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  135.36
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S,10R,16S)-16-((1S)-1-{(2R,3R)-3-[4-(chloromethyl)phenyl]oxiranyl}ethyl)-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone 、 三乙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到triethyl-[4-((2R,3R)-3-{(1S)-1-[(3S,10R,16S)-3-isobutyl-10-(4-methoxybenzyl)-2,5,9,12-tetraoxo-1-oxa-4,8,11-triazacyclohexadec-13-en-16-yl]ethyl}oxiranyl)benzyl]ammonium chloride
  参考文献：
  名称：

  Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide

  摘要：

  In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substituent (24, 30, and 31) showed increased solubility to MeOH and stronger cytotoxicity against KB cells in comparison with the parental 15,20-triamide analogue (2). Furthermore, the diethylamine analogue (30) exhibited in vivo anti-tumor activity against subcutaneously implanted murine sarcoma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.019
• 作为产物：
  描述：

  (3S,10R,16S)-16-{(1R)-3-[4-(hydroxymethyl)phenyl]-1-methylallyl}-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone 在 2,4,6-三甲基吡啶 、 二甲基二环氧乙烷 、 lithium chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 11.25h， 生成 (3S,10R,16S)-16-((1S)-1-{(2R,3R)-3-[4-(chloromethyl)phenyl]oxiranyl}ethyl)-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone
  参考文献：
  名称：

  Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide

  摘要：

  In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substituent (24, 30, and 31) showed increased solubility to MeOH and stronger cytotoxicity against KB cells in comparison with the parental 15,20-triamide analogue (2). Furthermore, the diethylamine analogue (30) exhibited in vivo anti-tumor activity against subcutaneously implanted murine sarcoma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.019