3-[(3-benzyl-5-thioxo-1,5-dihydro-(1,2,4)-triazol-4-yl)imino]-5-bromo-1,3-dihydro-indol-2-one | 898059-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[(3-benzyl-5-thioxo-1,5-dihydro-(1,2,4)-triazol-4-yl)imino]-5-bromo-1,3-dihydro-indol-2-one
• 英文别名: (3E)-3-[(3-benzyl-5-sulfanylidene-1H-1,2,4-triazol-4-yl)imino]-5-bromo-1H-indol-2-one
• CAS: 898059-71-7
• 化学式: C₁₇H₁₂BrN₅OS
• 分子量: 414.285
• InChiKey: ARFYJNBENFVJEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 聚合甲醛 、 3-[(3-benzyl-5-thioxo-1,5-dihydro-(1,2,4)-triazol-4-yl)imino]-5-bromo-1,3-dihydro-indol-2-one 以 甲醇 为溶剂， 反应 10.0h， 以63%的产率得到3-[(3-benzyl-5-thioxo-1,5-dihydro-(1,2,4)-triazol-4-yl)imino]-5-bromo-1-morpholin-4-ylmethyl-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Synthesis and bioevaluation of Schiff and Mannich bases of isatin derivatives with 4-amino-5-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

  摘要：

  Isatin (2,3-dioxindole) and its derivatives show a wide range of biological activities. In the present study, a series of Schiff and Mannich bases of isatin derivatives were prepared using 4-amino-5-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione. The structures of these derivatives were characterized by IR, H-1 NMR and elemental analysis. In vitro antimicrobial activities were evaluated by agar dilution method and the zone of inhibition values of these derivatives were compared with ciprofloxacin and fluconazole. Chloro and Bromo groups at fifth position of isatin broaden the spectrum of antibacterial activity against S. aures, P. aeruginoa, and E. coli, respectively. For the antifungal activity, the compound 6h showed equipotent activity against A. niger. The remaining majority of the compounds were found active in the biological screening. The efforts were also made to establish structure activity relationships among synthesized compounds.

  DOI：

  10.1007/s00044-011-9838-3
• 作为产物：
  描述：

  苯乙酸 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.08h， 生成 3-[(3-benzyl-5-thioxo-1,5-dihydro-(1,2,4)-triazol-4-yl)imino]-5-bromo-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and bioevaluation of Schiff and Mannich bases of isatin derivatives with 4-amino-5-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

  摘要：

  Isatin (2,3-dioxindole) and its derivatives show a wide range of biological activities. In the present study, a series of Schiff and Mannich bases of isatin derivatives were prepared using 4-amino-5-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione. The structures of these derivatives were characterized by IR, H-1 NMR and elemental analysis. In vitro antimicrobial activities were evaluated by agar dilution method and the zone of inhibition values of these derivatives were compared with ciprofloxacin and fluconazole. Chloro and Bromo groups at fifth position of isatin broaden the spectrum of antibacterial activity against S. aures, P. aeruginoa, and E. coli, respectively. For the antifungal activity, the compound 6h showed equipotent activity against A. niger. The remaining majority of the compounds were found active in the biological screening. The efforts were also made to establish structure activity relationships among synthesized compounds.

  DOI：

  10.1007/s00044-011-9838-3