zygosporamide | 916600-44-7

• 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: zygosporamide
• 英文别名: (3S,6S,9R,12S,15S)-3,12-dibenzyl-6,9,15-tris(2-methylpropyl)-1-oxa-4,7,10,13-tetrazacyclopentadecane-2,5,8,11,14-pentone
• CAS: 916600-44-7
• 化学式: C₃₆H₅₀N₄O₆
• 分子量: 634.816
• InChiKey: CKEAPQMIPHEQRF-LVIOGHJBSA-N

物化性质

• 沸点：
  930.588±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  zygosporamide 在 三乙胺 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii

  摘要：

  Zygosporamide (1), a new cyclic pentadepsipeptide, was isolated from the seawater-based fermentation broth of a marine-derived fungus identified as Zygosporium masonii. The structure of 1, which is composed of alpha-hydroxyleucic acid and both D-and L-amino acids, was determined by combined spectral and chemical methods. Despite a simple structure, zygosporamide illustrated significant cytotoxicity in the NCI's 60 cell line panel (median GI(50) = 9-1 mu M), with highly enhanced selectivity against the CNS cancer cell line SF-268 (GI(50) = 6.5 nM) and the renal cancer cell line RXF 393 (GI(50) <= 5.0 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.113
• 作为产物：
  描述：

  在 HATU 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 zygosporamide
  参考文献：
  名称：

  Synthesis and antitumor activity of cyclodepsipeptide zygosporamide and its analogues

  摘要：

  The synthesis and structure-activity relationships of zygosporamide, a known potent and selective cytotoxic natural product against SF-268 and RXF 393 cell lines, are described. The potencies of the synthetic zygosporamide are similar to those reported for the natural product toward all cancer cell lines examined with the exception of SF-268, the underlying cause of which remains to be elucidated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.066

文献信息

• Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii
  作者：Dong-Chan Oh、Paul R. Jensen、William Fenical

  DOI：10.1016/j.tetlet.2006.08.113

  日期：2006.11

  Zygosporamide (1), a new cyclic pentadepsipeptide, was isolated from the seawater-based fermentation broth of a marine-derived fungus identified as Zygosporium masonii. The structure of 1, which is composed of alpha-hydroxyleucic acid and both D-and L-amino acids, was determined by combined spectral and chemical methods. Despite a simple structure, zygosporamide illustrated significant cytotoxicity in the NCI's 60 cell line panel (median GI(50) = 9-1 mu M), with highly enhanced selectivity against the CNS cancer cell line SF-268 (GI(50) = 6.5 nM) and the renal cancer cell line RXF 393 (GI(50) <= 5.0 nM). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and antitumor activity of cyclodepsipeptide zygosporamide and its analogues
  作者：You Wang、Feiran Zhang、Yihua Zhang、Jun O. Liu、Dawei Ma

  DOI：10.1016/j.bmcl.2008.06.066

  日期：2008.8

  The synthesis and structure-activity relationships of zygosporamide, a known potent and selective cytotoxic natural product against SF-268 and RXF 393 cell lines, are described. The potencies of the synthetic zygosporamide are similar to those reported for the natural product toward all cancer cell lines examined with the exception of SF-268, the underlying cause of which remains to be elucidated. (c) 2008 Elsevier Ltd. All rights reserved.