(5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone | 779313-73-4

• 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: (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone
• 英文别名: (3S,6S,10S,11R,14S,15R,18S,21S)-14-amino-11-[(2S)-butan-2-yl]-10-hydroxy-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-6-propan-2-yl-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosane-2,5,8,13,17,20-hexone
• CAS: 779313-73-4
• 化学式: C₃₉H₆₁N₅O₁₀
• 分子量: 759.941
• InChiKey: CYYYFEWVAVHYLR-ZMRYFAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  207
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-prolyl [Hiv²]didemnin 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
• 作为产物：
  描述：

  (2S,3R)-3-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[(3S,4R,5S)-4-amino-5-methyl-3-tri(propan-2-yl)silyloxyheptanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-(4-methoxyphenyl)propanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid 在 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone
  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