(+/-)-3-octadecanamido-2-ethoxypropyl diphenyl phosphate | 131933-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (+/-)-3-octadecanamido-2-ethoxypropyl diphenyl phosphate
• 英文别名: [2-Ethoxy-3-(octadecanoylamino)propyl] diphenyl phosphate
• CAS: 131933-65-8
• 化学式: C₃₅H₅₆NO₆P
• 分子量: 617.807
• InChiKey: OAGHAXSECWASTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  43
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-3-octadecanamido-2-ethoxypropyl diphenyl phosphate 在 platinum(IV) oxide 氢气 、 2,3-二脱氧胞啶 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、99.98 kPa 条件下， 反应 97.67h， 生成 [(2S,3S,5R)-3-叠氮基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[2-乙氧基-3-(十八碳酰氨基)丙基]磷酸酯钠盐
  参考文献：
  名称：

  Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity

  摘要：

  Combinations of an amidoalkylphosphocholine, 8, and AZT have been found to cause an apparent synergistic action in suppressing infectious HIV-1 replication. In addition, amidoalkyl, oxyalkyl, and thioalkyl ether lipids have been chemically linked to anti-HIV-1 nucleosides (AZT and DDI) through phosphate and phosphonate linkages. These conjugates have shown promising in vitro anti-HIV-1 activity. Also, the conjugates have a 5-10-fold reduction in cell cytotoxicity compared to AZT alone. The most active compound, an amidoalkyl ether lipid-AZT conjugate, 4A, was found to have a differential selectivity of 1793 in a syncytial plaque assay. In comparison, AZT alone has a value of 1281.

  DOI：

  10.1021/jm00108a025
• 作为产物：
  描述：

  (+/-)-3-octadecanamido-2-ethoxy-1-propanol 、 氯磷酸二苯酯 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以60.1%的产率得到(+/-)-3-octadecanamido-2-ethoxypropyl diphenyl phosphate
  参考文献：
  名称：

  Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity

  摘要：

  Combinations of an amidoalkylphosphocholine, 8, and AZT have been found to cause an apparent synergistic action in suppressing infectious HIV-1 replication. In addition, amidoalkyl, oxyalkyl, and thioalkyl ether lipids have been chemically linked to anti-HIV-1 nucleosides (AZT and DDI) through phosphate and phosphonate linkages. These conjugates have shown promising in vitro anti-HIV-1 activity. Also, the conjugates have a 5-10-fold reduction in cell cytotoxicity compared to AZT alone. The most active compound, an amidoalkyl ether lipid-AZT conjugate, 4A, was found to have a differential selectivity of 1793 in a syncytial plaque assay. In comparison, AZT alone has a value of 1281.

  DOI：

  10.1021/jm00108a025

文献信息

• PIANTADOSI, CLAUDE;MARASCO, CANIO J. (JR);MORRIS-NATACHKE, SUSAN L.;MEYER+, J. MED. CHEM., 34,(1991) N, C. 1408-1414
  作者：PIANTADOSI, CLAUDE、MARASCO, CANIO J. (JR)、MORRIS-NATACHKE, SUSAN L.、MEYER+

  DOI：——

  日期：——
• ETHER LIPID-NUCLEOSIDE COVALENT CONJUGATES
  申请人：WAKE FOREST UNIVERSITY

  公开号：EP0533825A1

  公开（公告）日：1993-03-31
• EP0533825A4
  申请人：——

  公开号：EP0533825A4

  公开（公告）日：1993-06-02
• US5512671A
  申请人：——

  公开号：US5512671A

  公开（公告）日：1996-04-30
• [EN] ETHER LIPID-NUCLEOSIDE COVALENT CONJUGATES
  申请人：WAKE FOREST UNIVERSITY

  公开号：WO1991019726A1

  公开（公告）日：1991-12-26

  (EN) Ether lipid nucleoside covalent conjugates and derivatives thereof are disclosed, along with pharmaceutical compositions containing the same and methods of using the same to combat HIV-1 infections. Illustrative are 3'-Azido-3'-deoxythymidine-5'-monophosphate-D,L-3 octadecanamido-2-ethoxypropane and 3'-Azido-3'-deoxythymidine-5' butyrate-$g(g)-N,N,N-trimethyl-ammonium-$g(b)-(1-phospho-2-ethoxy-3-hexadecyloxypropane).(FR) Conjugués covalents de lipides d'éther et de nucléosides ainsi que leurs dérivés, compositions pharmaceutiques les contenant et procédés d'utilisation desdits conjugués afin de combattre des infections dues au VIH-1. On peut citer à titre d'exemple 3'-Azido-3'-désoxythymidine-5'-monophosphate-D,L-3-octadécanamido-2-éthoxypropane et 3'-Azido-3'-désoxythymidine-5'-butyrate-$g(g)-N,N,N-triméthyl-ammonium-$g(b)-(1-phospho-2-éthoxy-3-hexadécyloxypropane).