O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate | 329237-23-2

• 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: O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate
• 英文别名: cyclohexyl 3'-azido-3'-deoxythymidine-5'-yl H-phosphonate；2',3'-dideoxy-3'-azidothymidine 5'-cyclohexylphosphite；1-[(2R,4S,5S)-4-azido-5-(cyclohexyloxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 329237-23-2
• 化学式: C₁₆H₂₄N₅O₆P
• 分子量: 413.37
• InChiKey: CCNBPVVOMYBDHN-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 在 吡啶 、 potassium phosphate 、 三氯化磷 作用下， 以 二氯甲烷 、 水 、 formamide 、 乙腈 为溶剂， 反应 3.0h， 生成 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester
  参考文献：
  名称：

  P-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues

  摘要：

  P-(Alkyl)esters of AZT 5'-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded, AZT 5'-hydrogenphosphonate. The corresponding derivatives of d2A and d4T showed the same properties.

  DOI：

  10.1080/15257770008045461
• 作为产物：
  描述：

  3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 在 吡啶 、 potassium phosphate 、 三甲基乙酰氯 作用下， 以 水 、 formamide 、 乙腈 为溶剂， 生成 O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate
  参考文献：
  名称：

  P-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues

  摘要：

  P-(Alkyl)esters of AZT 5'-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded, AZT 5'-hydrogenphosphonate. The corresponding derivatives of d2A and d4T showed the same properties.

  DOI：

  10.1080/15257770008045461

文献信息

• Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates
  作者：Hua Fu、Yufen Zhao、Changxue Lin、Guangzhong Tu

  DOI：10.1055/s-2004-815939

  日期：——

  AZT/d4T phosphonates were synthesized by sequential condensation of AZT/d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

  AZT/d4T膦酸盐是通过在异戊酰氯存在下，依次将AZT/d4T与相应的醇或5′-DMT胸苷缩合合成的。这些膦酸盐依次进行硅烷化、硼化及在氨水中水解，得到抗HIV前药候选物AZT/d4T硼膦酸盐。
• A novel rearrangement in electrospray ionization multistage tandem mass spectrometry of amino acid ester cyclohexyl phosphoramidates of AZT
  作者：Yi Chen、Yingwu Yin、Xiaobin Sun、Xiaohong Liu、Haiyan Wang、Yufen Zhao

  DOI：10.1002/jms.834

  日期：2005.5

  Several amino acid ester cyclohexyl phosphoramidates of AZT as anti-HIV prodrugs were synthesized and investigated by electrospray ionization tandem mass spectrometry (ESI-MSn). A novel methoxy group migration from the carbonyl group to the phosphoryl group was observed in ESI-MS2. This migration is believed to be a general pathway for ions with a methyl ester moiety at the γ-position to a phosphoric acid moiety, which is assisted with metal ions such as Li+, Na+ and K+. Coordination between metal ions with both the carbonyl oxygen and phosphoryl oxygen might be a key factor responsible for this migration. Copyright © 2005 John Wiley & Sons, Ltd.

  合成并研究了几种AZT的氨基酸酯环己基磷酰胺酯作为抗HIV前药，采用电喷雾离子化串联质谱（ESI-MSn）。在ESI-MS2中观察到了一个新颖的甲氧基从羰基迁移到磷酸基团的现象。这种迁移被认为是γ位置具有甲基酯基团的离子向磷酸基团迁移的一种普遍途径，该过程受到Li+、Na+和K+等金属离子的协助。金属离子与羰基氧和磷酸氧之间的配位可能是导致这一迁移的关键因素。版权所有 © 2005 John Wiley & Sons, Ltd.
• Sun, Xiao Bin; Kang, Jian Xun; Zhao, Yu Fen, Chemical Communications, 2002, # 20, p. 2414 - 2415
  作者：Sun, Xiao Bin、Kang, Jian Xun、Zhao, Yu Fen

  DOI：——

  日期：——
• <i>P</i>-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues
  作者：A. L. Khandazhinskaya、E. A. Shirokova、I. L. Karpenko、N. F. Zakirova、N. B. Tarussova、A. A. Krayevsky

  DOI：10.1080/15257770008045461

  日期：2000.10

  P-(Alkyl)esters of AZT 5'-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded, AZT 5'-hydrogenphosphonate. The corresponding derivatives of d2A and d4T showed the same properties.