1-beta-D-阿拉伯糖呋喃基胞嘧啶 5'-二磷酸酯-1-O-十八烷基-2-O-棕榈酰-甘油 | 103383-67-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 1-beta-D-阿拉伯糖呋喃基胞嘧啶 5'-二磷酸酯-1-O-十八烷基-2-O-棕榈酰-甘油
• 中文别名: 1-beta-D-阿拉伯糖呋喃基胞嘧啶5'-二磷酸酯-1-O-十八烷基-2-O-棕榈酰-甘油
• 英文名称: 1-β-D-arabinofuranosylcytosine 5'-diphosphate-rac-1-O-octadecyl-2-O-palmitoylglycerol
• 英文别名: [1-[[[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3-octadecoxypropan-2-yl] hexadecanoate
• CAS: 103383-67-1
• 化学式: C₄₆H₈₇N₃O₁₄P₂
• 分子量: 968.156
• InChiKey: VZNJHZQSKLZCNH-JGJFOBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  65
• 可旋转键数：
  44
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  246
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  鲨肝醇 在 吡啶 、 boron trifluoride methanol complex 、 三乙胺 、 三氯氧磷 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 186.5h， 生成 1-beta-D-阿拉伯糖呋喃基胞嘧啶 5'-二磷酸酯-1-O-十八烷基-2-O-棕榈酰-甘油
  参考文献：
  名称：

  Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids

  摘要：

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.

  DOI：

  10.1021/jm00160a041

文献信息

• Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids
  作者：Chung Il Hong、Seung Ho An、David J. Buchheit、Alexander Nechaev、Alan J. Kirisits、Charles R. West、Wolfgang E. Berdel

  DOI：10.1021/jm00160a041

  日期：1986.10

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.