3-(2-bromoethyl)-3'-azido-3'-deoxythymidine | 189145-22-0

• 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-(2-bromoethyl)-3'-azido-3'-deoxythymidine
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3-(2-bromoethyl)-5-methylpyrimidine-2,4-dione
• CAS: 189145-22-0
• 化学式: C₁₂H₁₆BrN₅O₄
• 分子量: 374.194
• InChiKey: BJEOIIUTPSGXLO-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  齐多夫定	3'-azido-2',3'-deoxythymidine	30516-87-1	C10H13N5O4	267.244

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-(2-bromoethyl)-3'-azido-3'-deoxy-5'-O-(tert-butyldimethylsilyl)thymidine	189145-25-3	C18H30BrN5O4Si	488.457
  ——	1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3-[2-[3-[(2R,4S,5S)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]ethyl]-5-methylpyrimidine-2,4-dione	1054650-37-1	C34H56N10O8Si2	789.052

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethyl)-3'-azido-3'-deoxythymidine 在 咪唑 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 1-[(2R,4S,5S)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3-[2-[3-[(2R,4S,5S)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]ethyl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Preparation and Anti-HIV Activity of N-3-Substituted Thymidine Nucleoside Analogs

  摘要：

  A series of 22 derivatives of AZT substituted at the N-3 position of the thymine base were prepared and evaluated for anti-HIV activity in cell culture (Lai strain of HIV-1 in CEM-c113 cells). The AZT analogs bearing a N-3 amino group (7), a hydroxyalkyl chain (12f), and a phosphonomethyl (12k) substituent displayed activities in the 0.045-0.082 mu M range. The analogs 12d, 12e, 12q, 15, and 19 were active at <0.5 mu M concentration. Compound 18 in which two molecules of AZT are connected at N-3 via a two-carbon link and ''dimer'' II also displayed significant; activity. To obtain information concerning the mechanism of RT inhibition by these AZT analogs, compounds 7, 12d, 12e, and 12q were incubated with recombinant HIV-1 RT in the presence of poly(A)-oligo[dT((12-18))] and poly(C)-oligo[dG((12-18))] template-primers. In contrast to AZT-TP (control), none of these nucleosides displayed any significant inhibition of RT in the recombinant enzyme assay, indicating that phosphorylation is a necessary prerequiste for activity.

  DOI：

  10.1021/jm9600095
• 作为产物：
  描述：

  齐多夫定 、 1,2-二溴乙烷 在 sodium hydride 作用下， 生成 3-(2-bromoethyl)-3'-azido-3'-deoxythymidine
  参考文献：
  名称：

  Preparation and Anti-HIV Activity of N-3-Substituted Thymidine Nucleoside Analogs

  摘要：

  A series of 22 derivatives of AZT substituted at the N-3 position of the thymine base were prepared and evaluated for anti-HIV activity in cell culture (Lai strain of HIV-1 in CEM-c113 cells). The AZT analogs bearing a N-3 amino group (7), a hydroxyalkyl chain (12f), and a phosphonomethyl (12k) substituent displayed activities in the 0.045-0.082 mu M range. The analogs 12d, 12e, 12q, 15, and 19 were active at <0.5 mu M concentration. Compound 18 in which two molecules of AZT are connected at N-3 via a two-carbon link and ''dimer'' II also displayed significant; activity. To obtain information concerning the mechanism of RT inhibition by these AZT analogs, compounds 7, 12d, 12e, and 12q were incubated with recombinant HIV-1 RT in the presence of poly(A)-oligo[dT((12-18))] and poly(C)-oligo[dG((12-18))] template-primers. In contrast to AZT-TP (control), none of these nucleosides displayed any significant inhibition of RT in the recombinant enzyme assay, indicating that phosphorylation is a necessary prerequiste for activity.

  DOI：

  10.1021/jm9600095

文献信息

• Preparation and Anti-HIV Activity of N-3-Substituted Thymidine Nucleoside Analogs
  作者：David R. Adams、Caroline Perez、Michel Maillard、Jean-Claude Florent、Michel Evers、Yvette Hénin、Simon Litvak、Laura Litvak、Claude Monneret、David S. Grierson

  DOI：10.1021/jm9600095

  日期：1997.5.1

  A series of 22 derivatives of AZT substituted at the N-3 position of the thymine base were prepared and evaluated for anti-HIV activity in cell culture (Lai strain of HIV-1 in CEM-c113 cells). The AZT analogs bearing a N-3 amino group (7), a hydroxyalkyl chain (12f), and a phosphonomethyl (12k) substituent displayed activities in the 0.045-0.082 mu M range. The analogs 12d, 12e, 12q, 15, and 19 were active at <0.5 mu M concentration. Compound 18 in which two molecules of AZT are connected at N-3 via a two-carbon link and ''dimer'' II also displayed significant; activity. To obtain information concerning the mechanism of RT inhibition by these AZT analogs, compounds 7, 12d, 12e, and 12q were incubated with recombinant HIV-1 RT in the presence of poly(A)-oligo[dT((12-18))] and poly(C)-oligo[dG((12-18))] template-primers. In contrast to AZT-TP (control), none of these nucleosides displayed any significant inhibition of RT in the recombinant enzyme assay, indicating that phosphorylation is a necessary prerequiste for activity.