2-[1-(2,4-Dihydroxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide | 316142-73-1

• 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: 2-[1-(2,4-Dihydroxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide
• 英文别名: 1-[1-(2,4-dihydroxyphenyl)ethylideneamino]-3-phenylurea
• CAS: 316142-73-1
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: ALGGLWYXQVJIIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 4-苯基氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以56%的产率得到2-[1-(2,4-Dihydroxyphenyl)ethylidene]-N-phenylhydrazinecarboxamide
  参考文献：
  名称：

  Microwave-assisted Synthesis and Bioevaluation of Some Semicarbazones

  摘要：

  In continuation to our efforts in finding potential therapeutic agents, a variety of biologically significant semicarbazones were synthesized by the reaction of different carbonyl compounds with phenyl semicarbazides through microwave irradiation. Initially, 18 semicarbazones were studied for their antimicrobial, antitumor, and antioxidant potential. None of the tested compounds showed any antibacterial activity; however, some compounds showed significant antifungal activity. Interestingly, all compounds showed antitumor activity when tested against tumors grown on potato discs. These compounds were also tested for their effect on OH radical‐induced oxidative DNA damage. All the compounds showed DNA protection to varying extent. Based on the promising results of antitumor and antioxidant activities, another set of 24 semicarbazones was synthesized, and all of these semicarbazones were evaluated for their antioxidant potential. The results showed that the semicarbazones derived from 2‐nitrobenzaldehyde and acetophenone were the most active 2,2‐diphenyl‐1‐picrylhydrazyl 9 (DPPH) free radical scavengers. The overall results have led to the identification of some interesting compounds which seem to have great potential to be developed into effective anticancer drugs.

  DOI：

  10.1111/j.1747-0285.2012.01360.x

文献信息

• Microwave-assisted Synthesis and Bioevaluation of Some Semicarbazones
  作者：Laila Jafri、Farzana L. Ansari、Maryam Jamil、Saima Kalsoom、Sana Qureishi、Bushra Mirza

  DOI：10.1111/j.1747-0285.2012.01360.x

  日期：2012.6

  In continuation to our efforts in finding potential therapeutic agents, a variety of biologically significant semicarbazones were synthesized by the reaction of different carbonyl compounds with phenyl semicarbazides through microwave irradiation. Initially, 18 semicarbazones were studied for their antimicrobial, antitumor, and antioxidant potential. None of the tested compounds showed any antibacterial activity; however, some compounds showed significant antifungal activity. Interestingly, all compounds showed antitumor activity when tested against tumors grown on potato discs. These compounds were also tested for their effect on OH radical‐induced oxidative DNA damage. All the compounds showed DNA protection to varying extent. Based on the promising results of antitumor and antioxidant activities, another set of 24 semicarbazones was synthesized, and all of these semicarbazones were evaluated for their antioxidant potential. The results showed that the semicarbazones derived from 2‐nitrobenzaldehyde and acetophenone were the most active 2,2‐diphenyl‐1‐picrylhydrazyl 9 (DPPH) free radical scavengers. The overall results have led to the identification of some interesting compounds which seem to have great potential to be developed into effective anticancer drugs.