1-[(2R,4S,5S)-4-azido-5-[[octadecoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 158689-27-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5S)-4-azido-5-[[octadecoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 158689-27-1
• 化学式: C₂₈H₅₀N₅O₆P
• 分子量: 583.709
• InChiKey: IPQZPEKKTLOGCY-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-4-azido-5-[[octadecoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 selenium 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 Selenophosphoric acid O-[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester O'-octadecyl ester
  参考文献：
  名称：

  Xiao, Qiang; Sun, Jing; Sun, Qi, Synthesis, 2003, # 1, p. 107 - 111

  摘要：

  DOI：
• 作为产物：
  描述：

  齐多夫定 在 吡啶 作用下， 生成 1-[(2R,4S,5S)-4-azido-5-[[octadecoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Novel approach to the synthesis of AZT 5′-O-hydrogen phospholipids

  摘要：

  A series of AZT 5'-O-hydrogen phospholipids were synthesized by a tandem transesterification of diphenyl phosphite with AZT and a long-chain alcohol. The method possesses the merits of case of operation and high yields. It can also be extended to synthesize other biological phospholipids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01045-6

文献信息

• Synthesis of Novel Steroidal Bioconjugates with AZT and Phosphorus
  作者：Yong Ju、Peiyuan Jin、Kai Liu、Sanhao Ji、Yufen Zhao

  DOI：10.1055/s-2006-958966

  日期：2007.2

  Abstract: Some novel asymmetry steroidal phosphates, phospho-rothioates, phosphoroselenoates, and phosphoramidates were syn-thesized by oxidation or conjugation with amines using theAtherton–Todd reaction. The structures were confirmed by 1 HNMR, 31 P NMR, and ESI-MS spectroscopy. Key words: steroidal bioconjugate, AZT, phospholipid, phosphor-amidate Steroidal phosphates are important biological molecules

  摘要：利用阿瑟顿-托德反应通过氧化或与胺共轭合成了一些新的不对称甾体磷酸酯、硫代磷酸酯、硒代磷酸酯和氨基磷酸酯。通过 1 HNMR、 31 P NMR和ESI-MS光谱证实了结构。关键词：甾体生物偶联物，AZT，磷脂，氨基磷酸酯 甾体磷酸盐是重要的生物分子。据报道，某些甾体磷酸盐可显着增强淋巴细胞对植物血凝素的反应，增强白细胞介素-2和白细胞介素的产生体外人单核细胞的-3样活性、干扰素和肿瘤坏死因子。1 合成的哇巴因 1,5,19- 和 1,11,19-磷酸盐，它们是高极性和异常有效的钠泵抑制剂，稳定类固醇 A 环椅子构象并将 A 环锁定在半船构象中并减少 ABC 环部分的弯曲。2 在生物活性类固醇的研究中，Luu 等人
• Synthesis of Novel Steroidal Bioconjugates of Phospholipid with AZT
  作者：Pei-Yuan Jin、Kai Liu、Yong Ju、Yu-Fen Zhao

  DOI：10.1080/10426500701764874

  日期：2008.1.14

  Some novel asymmetry steroidal bioconjugates of phospholipid with AZT were synthesized by oxidation or conjugation with amines using Atherton-Todd reaction, and the structures were confirmed based on spectral methods. The result shown that some of bioconjugates possess activity against breast cancer MCF-7 in bioassay.