2-(7-hydroxy-2-oxochromen-4-yl)-N-[(2S,8S,12S,15S,21S,25S)-25-[[2-(7-hydroxy-2-oxochromen-4-yl)acetyl]amino]-1,4,7,14,17,20-hexamethyl-2,8,15,21-tetrakis(2-methylpropyl)-3,6,9,13,16,19,22,26-octaoxo-1,4,7,10,14,17,20,23-octazacyclohexacos-12-yl]acetamide | 1031272-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(7-hydroxy-2-oxochromen-4-yl)-N-[(2S,8S,12S,15S,21S,25S)-25-[[2-(7-hydroxy-2-oxochromen-4-yl)acetyl]amino]-1,4,7,14,17,20-hexamethyl-2,8,15,21-tetrakis(2-methylpropyl)-3,6,9,13,16,19,22,26-octaoxo-1,4,7,10,14,17,20,23-octazacyclohexacos-12-yl]acetamide
• CAS: 1031272-80-6
• 化学式: C₆₂H₈₆N₁₀O₁₆
• 分子量: 1227.42
• InChiKey: JKKSUXBRTXORBW-RYICAFHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  88
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  331
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  H-Dap(1)-N(Me)Leu-Sar-N(Me)Leu-(2).H-Dap(2)-N(Me)Leu-Sar-N(Me)Leu-(1) 、 7-羟基香豆素-4-乙酸 在 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 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 2-(7-hydroxy-2-oxochromen-4-yl)-N-[(2S,8S,12S,15S,21S,25S)-25-[[2-(7-hydroxy-2-oxochromen-4-yl)acetyl]amino]-1,4,7,14,17,20-hexamethyl-2,8,15,21-tetrakis(2-methylpropyl)-3,6,9,13,16,19,22,26-octaoxo-1,4,7,10,14,17,20,23-octazacyclohexacos-12-yl]acetamide
  参考文献：
  名称：

  Design and Synthesis of FAJANU: a de Novo C₂ Symmetric Cyclopeptide Family

  摘要：

  A novel cyclic peptide has been designed from several potent marine cytotoxic peptides, including IB-01212, luzopeptin, triostin, and thiocoraline. The FAJANU scaffold maintains C-2 symmetry, cyclic structure, and the construction of aromatic and aliphatic character at the N- and C-terminal extremes. A first six-member family was previously synthesized and evaluated biologically. Several analogues presented greater activity than IB-01212. Furthermore, on the basis of the most active candidate, we have performed a more exhaustive synthetic and structural analysis: (i) structure-activity relationship provided clues about the key elements in the framework, (ii) NMR assignment confirmed C-2, symmetry, and (iii) confocal images revealed its penetration and cellular localization.

  DOI：

  10.1021/jm800047b

文献信息

• Design and Synthesis of FAJANU: a de Novo <i>C</i>₂ Symmetric Cyclopeptide Family
  作者：Fayna Garcia-Martin、Luis J. Cruz、Ricard A. Rodriguez-Mias、Ernest Giralt、Fernando Albericio

  DOI：10.1021/jm800047b

  日期：2008.6.1

  A novel cyclic peptide has been designed from several potent marine cytotoxic peptides, including IB-01212, luzopeptin, triostin, and thiocoraline. The FAJANU scaffold maintains C-2 symmetry, cyclic structure, and the construction of aromatic and aliphatic character at the N- and C-terminal extremes. A first six-member family was previously synthesized and evaluated biologically. Several analogues presented greater activity than IB-01212. Furthermore, on the basis of the most active candidate, we have performed a more exhaustive synthetic and structural analysis: (i) structure-activity relationship provided clues about the key elements in the framework, (ii) NMR assignment confirmed C-2, symmetry, and (iii) confocal images revealed its penetration and cellular localization.