4-烯丙基-5-(4-氯苯基)-4H-1,2,4-噻唑-3-硫醇 | 91092-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-烯丙基-5-(4-氯苯基)-4H-1,2,4-噻唑-3-硫醇
• 中文别名: 4-烯丙基-5-(4-氯-苯基)-4H-[1,2,4]三唑-3-硫醇；5-(4-氯苯基)-4-丙-2-烯基-2H-1,2,4-三唑-3-硫酮；4-烯丙基-5-(4-氯苯基)-2H-1,2,4-三唑-3-硫酮
• 英文名称: 4-allyl-5-(4-chlorophenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 3-(4-chlorophenyl)-4-prop-2-enyl-1H-1,2,4-triazole-5-thione
• CAS: 91092-12-5
• 化学式: C₁₁H₁₀ClN₃S
• mdl: MFCD01046338
• 分子量: 251.739
• InChiKey: MYVPOZBQHZUCQD-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-(4-(2-bromoacetyl) piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 、 4-烯丙基-5-(4-氯苯基)-4H-1,2,4-噻唑-3-硫醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 以79.94%的产率得到7-(4-(2-((4-allyl-5-(4-chlorophenyl)-4H-1,2,4-triazol-3-yl)thio) acetyl) piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity

  摘要：

  New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).

  DOI：

  10.1016/j.bioorg.2019.102952
• 作为产物：
  描述：

  4-氯苯甲酸乙酯 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-烯丙基-5-(4-氯苯基)-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells

  摘要：

  A series of novel 1, 2, 4-triazole/ichalcone hybrids was prepared and identified with different spectroscopic techniques. The prepared compounds showed remarkable cytotoxic activity against different cancer cell lines. Compounds 24, 25, 27, 41 and 47 had shown the highest cytotoxicity among the tested compounds against human lung adenocarcinoma A549 cells with IC50 ranging from 4.4 to 16.04 mu M compared to cisplatin with IC50 of 153 mu M. Flow cytometric analysis of the tested compounds showed an increase in the number of apoptotic cells in a dose-dependent manner. The further mechanistic study demonstrated that 1, 2, 4-triazole-chalcone hybrids induced apoptosis via increased level of proapoptotic protein Bax, release of cytochrome c from mitochondria and activation of caspase-3/8/9 proteins. However, general caspase inhibition by the pan-caspase inhibitor, z-VAD-fmk, significantly decreased the apoptosis induced by the tested hybrids, suggesting dependency of apoptosis on activation of the caspase-3 pathway. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.073