5-<1(R,S),2-dihydroxyethyl>tetrazole | 84348-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-<1(R,S),2-dihydroxyethyl>tetrazole
• 英文别名: 5-<(1R,S)-1,2-dihydroxyethyl>tetrazole；5-[1(R,S),2-Dihydroxyethyl]tetrazole；1-(2H-tetrazol-5-yl)ethane-1,2-diol
• CAS: 84348-17-4
• 化学式: C₃H₆N₄O₂
• 分子量: 130.106
• InChiKey: SIHQAETUZNDKCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  94.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-(methoxycarbonyl)caffeoyl chloride 、 5-<1(R,S),2-dihydroxyethyl>tetrazole 在 吡啶 、 三乙胺 作用下， 以 苯 为溶剂， 以92%的产率得到[2-[(E)-3-[3,4-bis(methoxycarbonyloxy)phenyl]prop-2-enoyl]oxy-2-(2H-tetrazol-5-yl)ethyl] (E)-3-[3,4-bis(methoxycarbonyloxy)phenyl]prop-2-enoate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Hybrid Dicaffeoyltartaric/Diketo Acid and Tetrazole-Substituted l-Chicoric Acid Analogue Inhibitors of Human Immunodeficiency Virus Type 1 Integrase

  摘要：

  Fourteen analogues of the anti-HIV-1 integrase (IN) inhibitor L-chicoric acid (L-CA) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1 IN were determined in vitro, and their cell toxicities and EC50 against HIV-1 were measured in cells (ex vivo). Compounds 1-6 are catechol/beta-diketoacid hybrids, the majority of which exhibit submicromolar potency against 3'-end processing and strand transfer, though only with modest antiviral activities. Compounds 7-10 are L-CA/p-fluorobenzylpyrroloyl hybrids, several of which were more potent against strand transfer than 3'-end processing, a phenomenon previously attributed to the beta-diketo acid pharmacophore. Compounds 11-14 are tetrazole bioisosteres of L-CA and its analogues, whose in vitro potencies were comparable to L-CA but with enhanced antiviral potency. The trihydroxyphenyl analogue 14 was 30-fold more potent than L-CA at relatively nontoxic concentrations. These data indicate that L-CA analogues are attractive candidates for development into clinically relevant inhibitors of HIV-1 IN.

  DOI：

  10.1021/jm1010594