Lithium; (3aS,3bR,12S,12aR)-6,12-dihydroxy-2,5-dioxo-3a,3b,4,5,12,12a-hexahydro-1,3,7,9-tetraoxa-4-aza-2λ⁵-phospha-dicyclopenta[a,h]phenanthren-2-olate

• 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: Lithium; (3aS,3bR,12S,12aR)-6,12-dihydroxy-2,5-dioxo-3a,3b,4,5,12,12a-hexahydro-1,3,7,9-tetraoxa-4-aza-2λ⁵-phospha-dicyclopenta[a,h]phenanthren-2-olate
• 英文别名: Lithium narcistatin；lithium;(13R,14S,18R,19S)-9,19-dihydroxy-16-oxido-16-oxo-5,7,15,17-tetraoxa-12-aza-16λ5-phosphapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1(20),2,4(8),9-tetraen-11-one
• 化学式: C₁₄H₁₁NO₉P*Li
• 分子量: 375.157
• InChiKey: JTAWIFDITPSXMM-WAJBGZTRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.75
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (3aS,3bR,12S,12aR)-2,6,12-Trihydroxy-2-oxo-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-2λ⁵-phospha-dicyclopenta[a,h]phenanthren-5-one; compound with pyridine 在 Dowex 50W-X₂ (Li(+) form) 作用下， 以 水 为溶剂， 以77%的产率得到Lithium; (3aS,3bR,12S,12aR)-6,12-dihydroxy-2,5-dioxo-3a,3b,4,5,12,12a-hexahydro-1,3,7,9-tetraoxa-4-aza-2λ⁵-phospha-dicyclopenta[a,h]phenanthren-2-olate
  参考文献：
  名称：

  Antineoplastic Agents 500. Narcistatin^,1

  摘要：

  An efficient procedure was found for synthetic conversion of the sparingly soluble anticancer isocarbostyril narciclasine (1), a component of various Narcissus species, to a cyclic phosphate designated narcistatin (3b). The reaction between narciclasine, tetrabutylammonium. dihydrogen phosphate, and p-toluenesulfonic acid in pyridine afforded pyridinium narcistatin (3a) in reasonable yields. Transformation of narcistatin (3a) to, for example, the water-soluble prodrug sodium narcistatin (3d) was easily achieved by cation exchange chromatography. Narcistatin (3b) and 15 salt derivatives were evaluated against a panel of human cancer cell lines, and the range (0.1-0.01) of GI(50) values in mug/mL was found to parallel that shown by the parent narciclasine.

  DOI：

  10.1021/np020225i

文献信息

• Antineoplastic Agents 500. Narcistatin^,1
  作者：George R. Pettit、Noeleen Melody、Michael Simpson、Michael Thompson、Delbert L. Herald、John C. Knight

  DOI：10.1021/np020225i

  日期：2003.1.1

  An efficient procedure was found for synthetic conversion of the sparingly soluble anticancer isocarbostyril narciclasine (1), a component of various Narcissus species, to a cyclic phosphate designated narcistatin (3b). The reaction between narciclasine, tetrabutylammonium. dihydrogen phosphate, and p-toluenesulfonic acid in pyridine afforded pyridinium narcistatin (3a) in reasonable yields. Transformation of narcistatin (3a) to, for example, the water-soluble prodrug sodium narcistatin (3d) was easily achieved by cation exchange chromatography. Narcistatin (3b) and 15 salt derivatives were evaluated against a panel of human cancer cell lines, and the range (0.1-0.01) of GI(50) values in mug/mL was found to parallel that shown by the parent narciclasine.