3'-[3-(3-叠氮基-2,3-二脱氧-β-D-赤型-呋喃呋喃糖基)-3,6-二氢-5-甲基-2,6-二氧代-1(2H)-嘧啶基]-3'-脱氧胸苷 | 148665-49-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3'-[3-(3-叠氮基-2,3-二脱氧-β-D-赤型-呋喃呋喃糖基)-3,6-二氢-5-甲基-2,6-二氧代-1(2H)-嘧啶基]-3'-脱氧胸苷
• 英文名称: 3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine
• 英文别名: 3'-(3-(3-Azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-3'-deoxythymidine；1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 148665-49-0
• 化学式: C₂₀H₂₅N₇O₈
• 分子量: 491.461
• InChiKey: FOSHPJRCRHGLRP-KPRKPIBOSA-N

物化性质

• 熔点：
  >135°C (dec.)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine 在 四丁基氟化铵 、 sodium hydride 作用下， 反应 20.0h， 生成 3'-[3-(3-叠氮基-2,3-二脱氧-β-D-赤型-呋喃呋喃糖基)-3,6-二氢-5-甲基-2,6-二氧代-1(2H)-嘧啶基]-3'-脱氧胸苷
  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

• Serendipitous Discovery of a Zidovudine Guanidine Complex: A Superior Process for the Production of Zidovudine
  作者：Bruno K Radatus

  DOI：10.1021/op2000805

  日期：2011.11.18

  A superior process for the commercial production of zidovudine (AZT) has been developed. It was discovered that an AZT-guanidine complex formed when a crude zidovudine solution was treated with guanidine. This readily precipitated from protic solvents resulting in the exclusion of impurities and permitted the development of a superior isolation and purification of AZT.
• 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.