Pancratistatin 4-O-Phosphoric Acid | 670258-03-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: Pancratistatin 4-O-Phosphoric Acid
• 英文别名: [(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
• CAS: 670258-03-4
• 化学式: C₁₄H₁₆NO₁₁P
• 分子量: 405.255
• InChiKey: WNYLMOZZKDIAMD-SJVCOQNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Pancratistatin 4-O-Phosphoric Acid 在 magnesium acetate 作用下， 以 甲醇 为溶剂， 以0.010 g的产率得到magnesium 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+
• 作为产物：
  描述：

  水鬼蕉碱 在 Amberlite IR 120 H(+) resin 、 对甲苯磺酸 、 四丁基磷酸氢铵 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 水 为溶剂， 反应 48.0h， 生成 Pancratistatin 4-O-Phosphoric Acid
  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

• Pancratistatin cyclic phosphate prodrugs an phenpanstatin cyclic phosphate prodrugs
  申请人：Pettit R. George

  公开号：US20060128668A1

  公开（公告）日：2006-06-15

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

  使用四丁基氢氧化铵磷酸和二环己基碳二亚胺在吡啶中对苯酚丹（3a）进行选择性磷酸化，随后进行阳离子交换色谱分离，发现这是一种有效的制备新系列（3b-3d）有前途的3,4-O-环磷酸酯前药苯酚丹磷酸盐的途径。将类似的反应条件应用于百合碱（1a），得到一种单磷酸衍生物混合物，其中分离出了钠百合碱4-O-磷酸盐（4a），并通过X射线晶体学确认了其结构。改变反应条件后，直接对百合碱进行磷酸化，随后进行阳离子交换色谱分离，得到钠百合碱3,4-O-环磷酸盐（5b），被选为临床前开发的药物。
• PANCRATISTATIN CYCLIC PHOSPHATE PRODRUGS AND PHENPANSTATIN CYCLIC PHOSPHATE PRODRUGS
  申请人：Pettit George R.

  公开号：US20080139509A1

  公开（公告）日：2008-06-12

  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 (5b) which was selected for preclinical development.

  使用四丁基氢氧化铵磷酸和二环己基碳二亚胺在吡啶中选择性磷酸化苯酚喷丹霉素（3a），然后进行阳离子交换色谱过程，发现这是一种有效的方法，可以提供一系列有前途的3,4-O-环磷酸酯前药，称为苯酚喷丹霉素磷酸盐（3b-3d）。将类似的反应条件应用于喜马拉雅白花蒜碱（1a），导致单磷酸衍生物的混合物，其中分离出钠喜马拉雅白花蒜碱4-O-磷酸盐（4a），并通过X射线晶体学确认其结构。修改反应条件，直接磷酸化喜马拉雅白花蒜碱，然后进行阳离子交换色谱，以得到钠喜马拉雅白花蒜碱3,4-O-环磷酸盐（5b），该化合物被选为临床前开发的对象。
• Pancratistatin cyclic phosphate prodrugs and phenpanstatin cyclic phosphate prodrugs
  申请人：Arizona Board of Regents, a body corporate of the State of Arizona, acting for and on behalf of Arizona State University

  公开号：US07351830B2

  公开（公告）日：2008-04-01

  Selective phosphorylation of phenpanstatin (3a) with tetrabutylammonium dihydrogen phosphate and dicyclohexyl-carbodiimide in pyridine followed by cation exchange chromatographic procedures was found to provide an efficient mute 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 paancratistatin 4-O-phosphate (4a) was isolated and the structure confirmed by x-ray craxtallography. Modification of the reaction conditions allowed direct phosphorylation of pancratistatin followed by cation exchange chromatography to afford sodium pancratistatin 3,4-O-cyclic phosphate (5b) which was selected for preclinical development.

  通过在吡啶中使用四丁基氢氧化磷酸铵和二环己基碳二亚胺选择性磷酸化苯丙氨酮（3a），然后进行阳离子交换色谱程序，发现提供了一种有效的方法制备一系列有前途的3,4-O-环磷酸酯前药苯丙氨酮磷酸酯（3b-3d）。将类似的反应条件应用于鸟笼花碱（1a），导致单磷酸衍生物的混合物，其中分离出钠鸟笼花碱4-O-磷酸酯（4a），并通过X射线晶体学确认其结构。修改反应条件，直接磷酸化鸟笼花碱，然后进行阳离子交换色谱，得到钠鸟笼花碱3,4-O-环磷酸酯（5b），被选为临床前开发的药物。