N-[2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-(7H-purin-6-ylamino)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]amino]-2-oxoethyl]dodecanamide | 245749-58-0

• 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: N-[2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-(7H-purin-6-ylamino)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]amino]-2-oxoethyl]dodecanamide
• CAS: 245749-58-0
• 化学式: C₂₈H₄₅N₇O₅
• 分子量: 559.709
• InChiKey: MKNALEFSQQZFIY-GTJSMFJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-(7H-purin-6-ylamino)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]amino]-2-oxoethyl]dodecanamide 在 溶剂黄146 作用下， 反应 6.0h， 以75%的产率得到dodecyl-D-rhamnospicamycin
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2
• 作为产物：
  描述：

  在 甲醇 、 N-羟基丁二酰亚胺 、 氢气 、 silica gel 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 N-[2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-(7H-purin-6-ylamino)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]amino]-2-oxoethyl]dodecanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2