3-(2,4-dichloro-5-fluorophenyl)-6-[(2,4-dichlorophenoxy)methyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,4-dichloro-5-fluorophenyl)-6-[(2,4-dichlorophenoxy)methyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole
• 英文别名: 3-(2,4-Dichloro-5-fluorophenyl)-6-[(2,4-dichlorophenoxy)methyl]-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• 化学式: C₁₆H₇Cl₄FN₄OS
• 分子量: 464.134
• InChiKey: OBBGYFGIBNBGCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole 、 2,4-二氯苯氧乙酸 在 三氯氧磷 作用下， 反应 9.0h， 以78%的产率得到3-(2,4-dichloro-5-fluorophenyl)-6-[(2,4-dichlorophenoxy)methyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole
  参考文献：
  名称：

  Biological Studies of Some 2,4-Dichloro-5-fluorophenyl Containing Triazolothiadiazoles

  摘要：

  A series of dichlorofluorophenyl containing triazolothiadiazoles were obtained by cyclocondensation of triazole with substituted benzoic, aryloxyacetic, and anilinoacetic acids using POCl3 as cyclizing agent. The structures of the newly synthesized compounds were characterized and confirmed by IR, H-1 NMR, mass spectra, and elemental analysis. Selected compounds were screened for their antitubercular activity against Mycobacterium tuberculosis. The compound bearing 2,4-dichloro-5-fluorophenyl moiety at position 3, and 6 of the triazolothiadiazole showed excellent activity in vitro primary screening. Compounds with 3-chloro-4-fluorophenyl and 4-fluorophenoxymethyl moieties at position 6 of the triazolothiadiazole showed very good analgesic activity. Triazolothiadiazole with 4-chlorophenyl, 4-fluoro-3-phenoxyphenyl, and 2,4-dichloro-5-fluorophenyl moieties showed excellent antimicrobial activity against the tested strains at 6.25 mu g cm(-3) concentrations.

  DOI：

  10.1007/s00706-007-0718-y

文献信息

• Biological Studies of Some 2,4-Dichloro-5-fluorophenyl Containing Triazolothiadiazoles
  作者：Mari Sithambaram Karthikeyan、Bantwal Shivarama Holla、Balakrishna Kalluraya、Nalilu Suchetha Kumari

  DOI：10.1007/s00706-007-0718-y

  日期：2007.12

  A series of dichlorofluorophenyl containing triazolothiadiazoles were obtained by cyclocondensation of triazole with substituted benzoic, aryloxyacetic, and anilinoacetic acids using POCl3 as cyclizing agent. The structures of the newly synthesized compounds were characterized and confirmed by IR, H-1 NMR, mass spectra, and elemental analysis. Selected compounds were screened for their antitubercular activity against Mycobacterium tuberculosis. The compound bearing 2,4-dichloro-5-fluorophenyl moiety at position 3, and 6 of the triazolothiadiazole showed excellent activity in vitro primary screening. Compounds with 3-chloro-4-fluorophenyl and 4-fluorophenoxymethyl moieties at position 6 of the triazolothiadiazole showed very good analgesic activity. Triazolothiadiazole with 4-chlorophenyl, 4-fluoro-3-phenoxyphenyl, and 2,4-dichloro-5-fluorophenyl moieties showed excellent antimicrobial activity against the tested strains at 6.25 mu g cm(-3) concentrations.