(E)-(3S,10R,16S)-3-tert-Butyl-10-(4-methoxy-benzyl)-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone | 711028-26-1

• 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)-(3S,10R,16S)-3-tert-Butyl-10-(4-methoxy-benzyl)-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone
• CAS: 711028-26-1
• 化学式: C₃₄H₄₂N₂O₇
• 分子量: 590.717
• InChiKey: JDMPLRIMNVXDQR-UXPMXXBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-(3S,10R,16S)-3-tert-Butyl-10-(4-methoxy-benzyl)-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(3S,10R,13E,16S)-3-tert-butyl-10-[(4-methoxyphenyl)methyl]-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
  参考文献：
  名称：

  New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity

  摘要：

  Two analogues possessing steric hindered substituents on C-15 of arenastatin A (1), a potent cytotoxic spongean depsipeptide, were synthesized and shown to enhance stability in mouse serum. Notably, 15-tert-butylanalogue (6) with higher cytotoxicity exhibited in vivo anti-tumor activity through iv administration different from 1. Additionally, conformation analysis among the two analogues and arenastatin A (1) indicated that the torsion angle from C-14 to C-20 is a conclusive factor for the potent cytotoxicity of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.080
• 作为产物：
  描述：

  (S)-(-)-2-羟基-3,3-二甲基丁酸 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 四丁基碘化铵 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 (E)-(3S,10R,16S)-3-tert-Butyl-10-(4-methoxy-benzyl)-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone
  参考文献：
  名称：

  New analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, with anti-tumor activity

  摘要：

  Two analogues possessing steric hindered substituents on C-15 of arenastatin A (1), a potent cytotoxic spongean depsipeptide, were synthesized and shown to enhance stability in mouse serum. Notably, 15-tert-butylanalogue (6) with higher cytotoxicity exhibited in vivo anti-tumor activity through iv administration different from 1. Additionally, conformation analysis among the two analogues and arenastatin A (1) indicated that the torsion angle from C-14 to C-20 is a conclusive factor for the potent cytotoxicity of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.080