3'-azido-2',3'-didehydro-5'-O-methoxy-L-tryptophanyl thymidine | 268568-24-7

• 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: 3'-azido-2',3'-didehydro-5'-O-methoxy-L-tryptophanyl thymidine
• 英文别名: (S)-2-[3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxycarbonylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester；methyl (2S)-2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxycarbonylamino]-3-(1H-indol-3-yl)propanoate
• CAS: 268568-24-7
• 化学式: C₂₃H₂₅N₇O₇
• 分子量: 511.494
• InChiKey: YXWIOQXTHBGCGS-INDMIFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲胺 、 3'-azido-2',3'-didehydro-5'-O-methoxy-L-tryptophanyl thymidine 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到3'-azido-2',3'-didehydro-5'-O-methylamino-L-tryptopanyl thymidine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Amino Acid Carbamate Derivatives of AZT

  摘要：

  Lipophilic amino acid methyl ester and methyl amide carbamates of 3'-azido-3'-deoxythymidine (AZT) were synthesized and their anti-HIV-l activity in PBMCs was determined. The methyl amides were more potent (EC(50)s = 1.8 - 4.0 mu M) than the methyl esters (EC(50)s = 2.0 - 20 mu M). Carbamate hydrolysis by cell lysates and liberation of AZT was not observed for representative methyl ester or methyl amide AZT carbamates. No evidence of direct inhibition of HIV reverse transcriptase or integrase was observed.

  DOI：

  10.1080/15257770008032998
• 作为产物：
  描述：

  齐多夫定 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 19.0h， 生成 3'-azido-2',3'-didehydro-5'-O-methoxy-L-tryptophanyl thymidine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Amino Acid Carbamate Derivatives of AZT

  摘要：

  Lipophilic amino acid methyl ester and methyl amide carbamates of 3'-azido-3'-deoxythymidine (AZT) were synthesized and their anti-HIV-l activity in PBMCs was determined. The methyl amides were more potent (EC(50)s = 1.8 - 4.0 mu M) than the methyl esters (EC(50)s = 2.0 - 20 mu M). Carbamate hydrolysis by cell lysates and liberation of AZT was not observed for representative methyl ester or methyl amide AZT carbamates. No evidence of direct inhibition of HIV reverse transcriptase or integrase was observed.

  DOI：

  10.1080/15257770008032998

文献信息

• Synthesis and Antiviral Activity of Amino Acid Carbamate Derivatives of AZT
  作者：Shu-Ling Chang、George Griesgraber、Timothy W. Abraham、Tullika Garg、Heng Song、Cheryl L. Zimmerman、Carston R. Wagner

  DOI：10.1080/15257770008032998

  日期：2000.1

  Lipophilic amino acid methyl ester and methyl amide carbamates of 3'-azido-3'-deoxythymidine (AZT) were synthesized and their anti-HIV-l activity in PBMCs was determined. The methyl amides were more potent (EC(50)s = 1.8 - 4.0 mu M) than the methyl esters (EC(50)s = 2.0 - 20 mu M). Carbamate hydrolysis by cell lysates and liberation of AZT was not observed for representative methyl ester or methyl amide AZT carbamates. No evidence of direct inhibition of HIV reverse transcriptase or integrase was observed.