4-methyl-6-amino-8-[5'-O-(tert-butyldimethylsilyl)-2',3'-O-dilevylinyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine | 1065474-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-6-amino-8-[5'-O-(tert-butyldimethylsilyl)-2',3'-O-dilevylinyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine
• 英文别名: [(2R,3R,4R,5R)-5-(5-amino-7-methyl-2,6,7,9,11-pentazatricyclo[6.3.1.04,12]dodeca-1(12),3,5,8,10-pentaen-2-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(4-oxopentanoyloxy)oxolan-3-yl] 4-oxopentanoate
• CAS: 1065474-35-2
• 化学式: C₂₉H₄₂N₆O₈Si
• 分子量: 630.773
• InChiKey: CLSPADDXGGWCQV-TYYKAFGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-methyl-6-amino-8-[5'-O-(tert-butyldimethylsilyl)-2',3'-O-dilevylinyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 4-methyl-6-amino-8-[5'-O-L-valyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine
  参考文献：
  名称：

  Expedient Total Synthesis of Triciribine and Its Prodrugs

  摘要：

  Triciribine (TCN, 1) and its monophosphate (TCNP, 2) are tricyclic nucleotide derivatives that have potential antineoplastic activity. Triciribine inhibits the phosphorylation, activation, and signaling of Akt-1, -2, and -3, which may result in the inhibition of Akt-expressing tumor cell proliferation. Both TCN and TCNP have very low bioavailability, and the development of both drugs as intravenous (IV) treatments was halted because of the toxicity induced by the high doses needed for their use as general cytotoxic agents. This publication describes an expedient and straightforward total synthesis of amino acid prodrugs (3, 4) of TCN and TCNP. In our study, both the prodrugs significant improved the plasma exposure of the parent drugs and the prodrugs.

  DOI：

  10.1080/00397911.2010.524342
• 作为产物：
  描述：

  乙酰丙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 5.5h， 生成 4-methyl-6-amino-8-[5'-O-(tert-butyldimethylsilyl)-2',3'-O-dilevylinyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine
  参考文献：
  名称：

  WO2008/121941

  摘要：

  公开号：