5-[(E)-2-phenylethenyl]-1-(phenylsulfonyl)-1H-tetrazole | 1357019-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[(E)-2-phenylethenyl]-1-(phenylsulfonyl)-1H-tetrazole
• 英文别名: 1-(benzenesulfonyl)-5-[(E)-2-phenylethenyl]tetrazole
• CAS: 1357019-48-7
• 化学式: C₁₅H₁₂N₄O₂S
• 分子量: 312.352
• InChiKey: OEYKHVDBRAWWJB-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯磺酰氯 、 5-(BETA-苯乙烯基)-2H-1,2,3,4-四唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到5-[(E)-2-phenylethenyl]-1-(phenylsulfonyl)-1H-tetrazole
  参考文献：
  名称：

  RETRACTED: Proton-pumping-ATPase-targeted antifungal activity of cinnamaldehyde based sulfonyl tetrazoles

  摘要：

  Azoles are generally fungistatic, and resistance to fluconazole is emerging in several fungal pathogens. We designed a series of cinnamaldehyde based sulfonyl tetrazole derivatives. To further explore the antifungal activity, in vitro studies were conducted against 60 clinical isolates and 6 standard laboratory strains of Candida. The rapid irreversible action of these compounds on fungal cells suggested a membrane-located target for their action. Results obtained indicate plasma membrane H+-ATPase as site of action of the synthesized compounds. Inhibition of H+-ATPase leads to intracellular acidification and cell death. Presence of chloro and nitro groups on the sulfonyl pendant has been demonstrated to be a key structural element of antifungal potency. SEM micrographs of treated Candida cells showed severe cell breakage and alterations in morphology. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.007

文献信息

• RETRACTED: Proton-pumping-ATPase-targeted antifungal activity of cinnamaldehyde based sulfonyl tetrazoles
  作者：Sheikh Shreaz、Mohmmad Younus Wani、Sheikh Rayees Ahmad、Sheikh Imran Ahmad、Rimple Bhatia、Fareeda Athar、Manzoor Nikhat、Luqman A. Khan

  DOI：10.1016/j.ejmech.2011.12.007

  日期：2012.2

  Azoles are generally fungistatic, and resistance to fluconazole is emerging in several fungal pathogens. We designed a series of cinnamaldehyde based sulfonyl tetrazole derivatives. To further explore the antifungal activity, in vitro studies were conducted against 60 clinical isolates and 6 standard laboratory strains of Candida. The rapid irreversible action of these compounds on fungal cells suggested a membrane-located target for their action. Results obtained indicate plasma membrane H+-ATPase as site of action of the synthesized compounds. Inhibition of H+-ATPase leads to intracellular acidification and cell death. Presence of chloro and nitro groups on the sulfonyl pendant has been demonstrated to be a key structural element of antifungal potency. SEM micrographs of treated Candida cells showed severe cell breakage and alterations in morphology. (C) 2011 Elsevier Masson SAS. All rights reserved.