5-Nitro-1-(2,3,3-triiodo-allyl)-1H-[1,2,4]triazole

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-Nitro-1-(2,3,3-triiodo-allyl)-1H-[1,2,4]triazole
• 英文别名: 5-Nitro-1-(2,3,3-triiodoallyl)-1,2,4-triazole；5-nitro-1-(2,3,3-triiodoprop-2-enyl)-1,2,4-triazole
• 化学式: C₅H₃I₃N₄O₂
• 分子量: 531.818
• InChiKey: WEJJJHSGSVRKCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硝基-1,2,4-三氮唑 、 2,3,3-triodoallyl 4-methylbenzenesulfonate 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以46%的产率得到5-Nitro-1-(2,3,3-triiodo-allyl)-1H-[1,2,4]triazole
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationship analysis of N-triiodoallyl- and N-iodopropargylazoles. New antifungal agents

  摘要：

  New series of N-(2,3,3-triiodoallyl) and N-(3-iodopropargyl) azole derivatives (100 compounds) involving pyrrole, pyrazole, imidazole, triazole, and tetrazole nuclei were synthesized successively with the aid of quantitative structure-activity relationship (QSAR) analysis to obtain potent antifungal agents. Starting from the derivatives of nitropyrrole-containing antibiotics, the QSAR analysis of the pyrrole derivatives against Candida albicans and Trichophyton mentagrophytes strains indicated the positive contribution of the nitro group and negative effect of the size of molecule. Further application of the QSAR analysis on the multi-azole derivatives revealed the importance of hydrophobicity and electronegativity as well as steric effect to the activities and led to the synthesis of one of the most potent iodo compounds, 2-(2,3,3-triiodoallyl)tetrazole (67, ME1401).

  DOI：

  10.1021/jm00386a019

文献信息

• Synthesis and quantitative structure-activity relationship analysis of N-triiodoallyl- and N-iodopropargylazoles. New antifungal agents
  作者：Masao Koyama、Noriko Ohtani、Fumio Kai、Ikuo Moriguchi、Shigeharu Inouye

  DOI：10.1021/jm00386a019

  日期：1987.3

  New series of N-(2,3,3-triiodoallyl) and N-(3-iodopropargyl) azole derivatives (100 compounds) involving pyrrole, pyrazole, imidazole, triazole, and tetrazole nuclei were synthesized successively with the aid of quantitative structure-activity relationship (QSAR) analysis to obtain potent antifungal agents. Starting from the derivatives of nitropyrrole-containing antibiotics, the QSAR analysis of the pyrrole derivatives against Candida albicans and Trichophyton mentagrophytes strains indicated the positive contribution of the nitro group and negative effect of the size of molecule. Further application of the QSAR analysis on the multi-azole derivatives revealed the importance of hydrophobicity and electronegativity as well as steric effect to the activities and led to the synthesis of one of the most potent iodo compounds, 2-(2,3,3-triiodoallyl)tetrazole (67, ME1401).