1-[(2R,4S,5S)-4-azido-5-[[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-oxidophosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 329237-30-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-[(2R,4S,5S)-4-azido-5-[[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-oxidophosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 329237-30-1
• 化学式: C₃₇H₅₈N₅O₆P
• 分子量: 699.871
• InChiKey: VOTWMHLFISUUIY-AFLLIHSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 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-[[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-oxidophosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 selenium 作用下， 以 水 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of Novel Steroidal Bioconjugates of Phospholipid with AZT

  摘要：

  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.

  DOI：

  10.1080/10426500701764874
• 作为产物：
  描述：

  司他夫定 在 吡啶 、 potassium phosphate 、 三甲基乙酰氯 、 三氯化磷 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 1-[(2R,4S,5S)-4-azido-5-[[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-oxidophosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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 Novel Dimeric Steroidal-nucleoside Phosphoramidates
  作者：Sanhao Ji、Qiang Xiao、Yong Ju、Yufen Zhao

  DOI：10.1246/cl.2005.944

  日期：2005.7

  Some dimeric steroidal conjugated with 3′-azido-3′-deoxythymidine (AZT) as potential membrane-soluble prodrugs of the phosphate forms were synthesized in good yields and the structures were confirm...

  以良好的收率合成了一些与 3'-叠氮基-3'-脱氧胸苷 (AZT) 结合的二聚体甾体化合物作为磷酸酯形式的潜在膜溶性前药，并确认了结构......
• 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.
• <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.