(E)-(2S,8R,15R)-15-Isobutyl-8-(4-methoxy-benzyl)-2-((E)-(R)-1-methyl-3-phenyl-allyl)-1-oxa-7,10-diaza-cyclohexadec-4-ene-6,9,13,16-tetraone | 302600-53-9

• 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: (E)-(2S,8R,15R)-15-Isobutyl-8-(4-methoxy-benzyl)-2-((E)-(R)-1-methyl-3-phenyl-allyl)-1-oxa-7,10-diaza-cyclohexadec-4-ene-6,9,13,16-tetraone
• 英文别名: (2S,4E,8R,15R)-8-[(4-methoxyphenyl)methyl]-15-(2-methylpropyl)-2-[(E,2R)-4-phenylbut-3-en-2-yl]-1-oxa-7,10-diazacyclohexadec-4-ene-6,9,13,16-tetrone
• CAS: 302600-53-9
• 化学式: C₃₅H₄₄N₂O₆
• 分子量: 588.744
• InChiKey: QMNRUFXOYDMDJQ-XXUOYRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(2S,8R,15R)-15-Isobutyl-8-(4-methoxy-benzyl)-2-((E)-(R)-1-methyl-3-phenyl-allyl)-1-oxa-7,10-diaza-cyclohexadec-4-ene-6,9,13,16-tetraone 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到(E)-(2S,8R,15R)-15-Isobutyl-8-(4-methoxy-benzyl)-2-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-1-oxa-7,10-diaza-cyclohexadec-4-ene-6,9,13,16-tetraone
  参考文献：
  名称：

  Synthesis and biological property of carba and 20-Deoxo analogues of arenastatin A

  摘要：

  The carba analogue, in which a methylene group is substituted for the oxygen atom linked to C-15, and 20-deoxo analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, were synthesized. Both analogues lacking the 15,20-ester function, which was easily metabolized in serum, showed good stability in serum as well as moderate cytotoxic activity against KB cells and better solubility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00356-5
• 作为产物：
  描述：

  (R)-6-Amino-2-isobutyl-4-oxo-hexanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester; hydrochloride 在 二苯基磷酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-(2S,8R,15R)-15-Isobutyl-8-(4-methoxy-benzyl)-2-((E)-(R)-1-methyl-3-phenyl-allyl)-1-oxa-7,10-diaza-cyclohexadec-4-ene-6,9,13,16-tetraone
  参考文献：
  名称：

  Synthesis and biological property of carba and 20-Deoxo analogues of arenastatin A

  摘要：

  The carba analogue, in which a methylene group is substituted for the oxygen atom linked to C-15, and 20-deoxo analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, were synthesized. Both analogues lacking the 15,20-ester function, which was easily metabolized in serum, showed good stability in serum as well as moderate cytotoxic activity against KB cells and better solubility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00356-5

文献信息

• Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide
  作者：Nobutoshi Murakami、Satoru Tamura、Weiqi Wang、Tatsuya Takagi、Motomasa Kobayashi

  DOI：10.1016/s0040-4020(01)00339-8

  日期：2001.5

  In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A. (C) 2001 Elsevier Science Ltd. All rights reserved.