rac-1-十六烷基-2-棕榈酰甘油-3-磷酸 | 103383-64-8

• 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: rac-1-十六烷基-2-棕榈酰甘油-3-磷酸
• 英文名称: rac-1-O-hexadecyl-2-O-palmitoylglycerol 3-phosphate
• 英文别名: rac-1-hexadecyl-2-palmitoylglycero-3-phosphoric acid；(1-Hexadecoxy-3-phosphonooxypropan-2-yl) hexadecanoate
• CAS: 103383-64-8
• 化学式: C₃₅H₇₁O₇P
• 分子量: 634.918
• InChiKey: VHSFYIPCRZJPED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  43
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-1-十六烷基-2-棕榈酰甘油-3-磷酸 、 1-β-D-arabinofuranosylcytosine 5'-monophosphoromorpholidate 4-morpholine N,N'-dicyclohexylcarboxamidinium salt 在 吡啶 作用下， 反应 120.0h， 以30%的产率得到1-β-D-arabinofuranosylcytosine 5'-diphosphate-rac-1-O-hexadecyl-2-O-palmitoylglycerol disodium salt
  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
• 作为产物：
  描述：

  溴代十六烷 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium amide 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 正己烷 、 甲苯 、 苯 为溶剂， 25.0~70.0 ℃ 、344.73 kPa 条件下， 反应 90.0h， 生成 rac-1-十六烷基-2-棕榈酰甘油-3-磷酸
  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

• Novozhilova, T. I.; Malekin, S. I.; Kozhukhov, V. I., Russian Journal of Bioorganic Chemistry, 2000, vol. 26, # 3, p. 213 - 215
  作者：Novozhilova, T. I.、Malekin, S. I.、Kozhukhov, V. I.、Kruglyak, Yu. L.、Kurochkin, V. K.

  DOI：——

  日期：——
• Khromova; Malekin; Kisin, Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 4, p. 268 - 272
  作者：Khromova、Malekin、Kisin、Nosova、Kruglyak、Kurochkin

  DOI：——

  日期：——
• 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.