quinium pancratistatin 4-O-hydrogenphosphate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: quinium pancratistatin 4-O-hydrogenphosphate
• 英文别名: Quinium Pancratistatin 4-O-Phosphate；[(1R,2S,3R,4S,4aR,11bR)-1,2,3,7-tetrahydroxy-6-oxo-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-4-yl] dihydrogen phosphate;(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• 化学式: C₁₄H₁₆NO₁₁P*C₂₀H₂₄N₂O₂
• 分子量: 729.678
• InChiKey: XKPRZTFGAMRRCK-KSTFCGCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.99
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  245
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  奎宁 、 Pancratistatin 4-O-Phosphoric Acid 以 甲醇 为溶剂， 反应 96.0h， 以0.015 g的产率得到quinium pancratistatin 4-O-hydrogenphosphate
  参考文献：
  名称：

  Antineoplastic Agents. 511. Direct Phosphorylation of Phenpanstatin and Pancratistatin

  摘要：

  Selective phosphorylation of phenpanstatin (3a) with tetrabutylammonium dihydrogen phosphate and dicyclohexylcarbodiimide in pyridine followed by cation-exchange chromatographic procedures was found to provide an efficient route to a new series (3b-3d) of promising 3,4-O-cyclic phosphate prodrugs designated phenpanstatin phosphates. Application of analogous reaction conditions to pancratistatin (1a) led to a mixture of monophosphate derivatives where sodium pancratistatin 4-O-phosphate (4a) was isolated and the structure confirmed by X-ray crystallography. Modification of the reaction conditions allowed direct phosphorylation of pancratistatin followed by cation-exchange chromatography to afford sodium pancratistatin 3,4-O-cyclic phosphate (5a), which was selected for preclinical development.

  DOI：

  10.1021/np030299+

文献信息

• Antineoplastic Agents. 511. Direct Phosphorylation of Phenpanstatin and Pancratistatin
  作者：George R. Pettit、Noeleen Melody、Delbert L. Herald

  DOI：10.1021/np030299+

  日期：2004.3.1

  Selective phosphorylation of phenpanstatin (3a) with tetrabutylammonium dihydrogen phosphate and dicyclohexylcarbodiimide in pyridine followed by cation-exchange chromatographic procedures was found to provide an efficient route to a new series (3b-3d) of promising 3,4-O-cyclic phosphate prodrugs designated phenpanstatin phosphates. Application of analogous reaction conditions to pancratistatin (1a) led to a mixture of monophosphate derivatives where sodium pancratistatin 4-O-phosphate (4a) was isolated and the structure confirmed by X-ray crystallography. Modification of the reaction conditions allowed direct phosphorylation of pancratistatin followed by cation-exchange chromatography to afford sodium pancratistatin 3,4-O-cyclic phosphate (5a), which was selected for preclinical development.