dehydrotamandarin A

• 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: dehydrotamandarin A
• 英文别名: dehydrotamandarin-A；(2S)-N-[(2R)-1-[[(3S,6S,10S,11R,14S,15R,18S,21S)-11-[(2S)-butan-2-yl]-10-hydroxy-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6-propan-2-yl-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
• 化学式: C₅₄H₈₃N₇O₁₄
• 分子量: 1054.29
• InChiKey: CRMQSDHAUJOQIE-MRIHCXOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  75
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  268
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  L-缬氨酸 在 palladium on activated charcoal 、 四丁基碘化铵 吗啉 、 N-甲基吗啉 、 盐酸 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 硫酸 、 氢气 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 magnesium bromide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 dehydrotamandarin A
  参考文献：
  名称：

  Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs

  摘要：

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

  DOI：

  10.1021/ja010222c

文献信息

• Synthetic methods for aplidine and new antitumoral derivatives, methods of making and using them
  申请人：Rodriguez Ignacio

  公开号：US20080009435A1

  公开（公告）日：2008-01-10

  The invention relates to aplidine derivatives of the general formula: which are useful for the treatment of tumors.

  本发明涉及一种通式为的aplidine衍生物，其可用于治疗肿瘤。
• US7348310B2
  申请人：——

  公开号：US7348310B2

  公开（公告）日：2008-03-25
• US7678765B2
  申请人：——

  公开号：US7678765B2

  公开（公告）日：2010-03-16
• Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs
  作者：Bo Liang、David J. Richard、Padma S. Portonovo、Madeleine M. Joullié

  DOI：10.1021/ja010222c

  日期：2001.5.1

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.