tamandarin B | 258339-38-7

• 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: tamandarin B
• 英文别名: (2S)-N-[(2R)-1-[[(3S,6S,10S,11R,14S,15R,18S,21S)-10-hydroxy-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(propan-2-yl)-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-[(2S)-2-hydroxypropanoyl]-N-methylpyrrolidine-2-carboxamide
• CAS: 258339-38-7
• 化学式: C₅₃H₈₃N₇O₁₄
• 分子量: 1042.28
• InChiKey: VFCVQRSICIMDEG-JTWNPRKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  74
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  271
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 tamandarin B 在 sodium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 75.0h， 生成 (S)-2-({(S)-1-[(S)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid methyl ester 、 (3S,4R)-3-Hydroxy-4-[(2S,3R)-3-hydroxy-2-((R)-2-{[(S)-1-((S)-2-hydroxy-propionyl)-pyrrolidine-2-carbonyl]-methyl-amino}-4-methyl-pentanoylamino)-butyrylamino]-5-methyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Tamandarins A and B:  New Cytotoxic Depsipeptides from a Brazilian Ascidian of the Family Didemnidae

  摘要：

  The structures of two new, naturally occurring cytotoxic depsipeptides, tamandarins A and B (1 and 2), are presented. The tamandarins were isolated from an unidentified Brazilian marine ascidian of the family Didemnidae. The structures of the new cytotoxins were assigned by interpretation of FABMS data and by extensive 2D NMR analyses. The absolute configurations of the tamandarins were assigned by acid and alkaline hydrolysis to yield their corresponding amino acids, which were then analyzed as their Marfey derivatives. The cytotoxicity of tamandarin A (1) was evaluated against various human cancer cell lines and shown to be slightly more potent than didemnin B. A. qualitative discussion of the conformation of tamandarin A (1) in solution, obtained from NMR J-value data, variable temperature experiments, and NOESY/ROESY data, is included.

  DOI：

  10.1021/jo991425a
• 作为产物：
  描述：

  L-缬氨酸 在 palladium on activated charcoal 、 四丁基碘化铵 吗啉 、 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 硫酸 、 氢气 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 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 为溶剂， 反应 16.0h， 生成 tamandarin B
  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

• Total synthesis of (−)-tamandarin B
  作者：Madeleine M Joullié、Padma Portonovo、Bo Liang、David J Richard

  DOI：10.1016/s0040-4039(00)01409-x

  日期：2000.12

  The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.
• Synthetic Studies of Tamandarin B Side Chain Analogues
  作者：Kenneth M. Lassen、Jisun Lee、Madeleine M. Joullié

  DOI：10.1021/jo100457w

  日期：2010.5.7

  The syntheses of three tamandarin B analogues are described. The goal of these studies was to prepare material to determine their relative therapeutic index and to gain an oversight as to their potential for clinical applications.
• US7348310B2
  申请人：——

  公开号：US7348310B2

  公开（公告）日：2008-03-25
• 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.
• Tamandarins A and B:  New Cytotoxic Depsipeptides from a Brazilian Ascidian of the Family Didemnidae
  作者：Hélène Vervoort、William Fenical、Rosângela de A. Epifanio

  DOI：10.1021/jo991425a

  日期：2000.2.1

  The structures of two new, naturally occurring cytotoxic depsipeptides, tamandarins A and B (1 and 2), are presented. The tamandarins were isolated from an unidentified Brazilian marine ascidian of the family Didemnidae. The structures of the new cytotoxins were assigned by interpretation of FABMS data and by extensive 2D NMR analyses. The absolute configurations of the tamandarins were assigned by acid and alkaline hydrolysis to yield their corresponding amino acids, which were then analyzed as their Marfey derivatives. The cytotoxicity of tamandarin A (1) was evaluated against various human cancer cell lines and shown to be slightly more potent than didemnin B. A. qualitative discussion of the conformation of tamandarin A (1) in solution, obtained from NMR J-value data, variable temperature experiments, and NOESY/ROESY data, is included.