2-(1'-iodopropyn-3'-yl)-5-(p-methylphenyl)tetrazole | 92712-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1'-iodopropyn-3'-yl)-5-(p-methylphenyl)tetrazole
• 英文别名: 2-(3-Iodoprop-2-ynyl)-5-(p-tolyl)tetrazole；2-(3-iodoprop-2-ynyl)-5-(4-methylphenyl)tetrazole
• CAS: 92712-23-7
• 化学式: C₁₁H₉IN₄
• 分子量: 324.124
• InChiKey: DKHBCCALGSWZQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-Methylphenyl)-2-prop-2-ynyltetrazole 在 morpholine-iodine complex 作用下， 以 苯 为溶剂， 反应 16.0h， 以37%的产率得到2-(1'-iodopropyn-3'-yl)-5-(p-methylphenyl)tetrazole
  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

• Tetrazole compounds, process for preparing the same and antibacterial and antifungal compositions containing the same as active ingredient
  申请人：MEIJI SEIKA KAISHA LTD.

  公开号：EP0107859A1

  公开（公告）日：1984-05-09

  Triiodallyl- or iodopropargyl-substituted tetrazole compounds which are prepared by racting substituted tetrazole compound with reactive derivatives of corresponding triiodoally alcohol or iodopropargyl alcohol or by iodinating propargyltetrazole compounds, as well as antibacterial and antifungal compositions for medicinal, agricultural and industrial fields which contain as active ingredient said tetrazole compounds.

  通过将取代的四唑化合物与相应的三碘醇或碘丙炔醇的活性衍生物反应，或通过碘化丙炔基四唑化合物制备的三碘醇或碘丙炔基取代的四唑化合物，以及含有上述四唑化合物作为活性成分的用于医药、农业和工业领域的抗菌和抗真菌组合物。
• US4647572A
  申请人：——

  公开号：US4647572A

  公开（公告）日：1987-03-03
• 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).