Phenyl-[1-(2,3,3-triiodo-allyl)-1H-pyrrol-2-yl]-methanone | 106191-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl-[1-(2,3,3-triiodo-allyl)-1H-pyrrol-2-yl]-methanone
• 英文别名: Phenyl-[1-(2,3,3-triiodoallyl)pyrrol-2-yl]methanone；phenyl-[1-(2,3,3-triiodoprop-2-enyl)pyrrol-2-yl]methanone
• CAS: 106191-73-5
• 化学式: C₁₄H₁₀I₃NO
• 分子量: 588.953
• InChiKey: RBMDJCJPXIFDLM-UHFFFAOYSA-N

物化性质

• 沸点：
  468.4±45.0 °C(Predicted)
• 密度：
  2.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯甲酰基吡咯 、 2,3,3-triodoallyl 4-methylbenzenesulfonate 在 sodium hydroxide 作用下， 生成 Phenyl-[1-(2,3,3-triiodo-allyl)-1H-pyrrol-2-yl]-methanone
  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).