A convenient synthesis, reactions and biological studies of some novel selenolo[2,3-c]pyrazole compounds as antimicrobial and anti-inflammatory agents

作者：Zaki Remon M^*; El Ossaily Yasser A; Geies Ahmed A

来源：Medicinal Chemistry Research, 2016, 25(5): 893-908.

DOI：10.1007/s00044-016-1536-8

• Synthesis
• Reactions
• Selenolopyrazole
• Pyrimidine
• Antimicrobial activity
• Anti-inflammatory activity

5-Chloro-3-methyl-1-phenylpyrazole-4-carbonitrile 3 was reacted with selenium in the presence of sodium borohydride and chloroacetamide to afford selanyl acetamide 5, which underwent Thorpe-Ziegler cyclization upon heating with sodium ethoxide to give the novel synthesized 4-amino-3-methyl-1-phenyl-1H-selenolo[2,3-c]pyrazole-5-carboxamide compound (6). The latter compound was used as a versatile precursor for synthesis of other heterocyclic rings, namely pyrimidine, imidazopyrimidine and thiadiazinopyrimidine fused to selenolo[2,3-c]pyrazole moiety. The newly synthesized compounds and their derivatives were characterized by elemental and spectral analysis (IR, H-1 NMR, C-13 NMR and mass spectrometric analyses). Furthermore, some of these synthesized compounds were screened against various pathogenic bacterial and fungal strains. The results demonstrate that most of the synthesized compounds possess a significant antibacterial activity against gram-positive and gram-negative bacteria. Also, some of these compounds showed a remarkable antifungal activity, especially Candida albicans. On the other hand, some of the synthesized compounds possess high anti-inflammatory activity using carrageenan-induced rat paw edema assay compared with indomethacin.
The present work discussed synthesis of new selenolo[2,3-c]pyrazoles fused to other heterocyclic rings, namely pyrimidine, imidazopyrimidine and thiadiazinopyrimidine. Some of the synthesized compounds showed remarkable antibacterial, antifungal and anti-inflammatory activities.

• 出版日期2016-5