ANTI-INFLAMMATORY AND ANTIMICROBIAL ACTIVITY OF 4,5-DIHYDROPYRIMIDINE-5-CARBONITRILE DERIVATIVES: THEIR SYNTHESIS AND SPECTRAL ELUCIDATION

作者：Alam Mohammad Mumtaz; Akhter Mymoona; Husain Asif; Marella Akranth; Tanwar Om Prakash; Ali Rahmat; Hasan Syed Mi**ahul; Kumar Harish; Haider Rashiduddin; Shaquiquzzaman Mohammad^*

来源：Acta Poloniae Pharmaceutica, 2012, 69(6): 1077-1085.

• cyanopyrimidine
• Schiff's base
• anti-inflammatory
• analgesic
• antimicrobial

Thirteen new 6-(1-H-indole-2-y1)-4-oxo-242-(substituted-benzylidene)-hydrazinyll-4,5-dihydropyrimidine-5-carbonitrile derivatives were synthesized. The title compounds, hydrazones, were synthesized by reaction of hydrazine group of 2-hydraziny1-4-(1-H-indole-2-y1)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (2) with different substituted aromatic aldehydes using a mixture (2:8, v/v) of glacial acetic acid and alcohol. The required intermediate compound 2 was synthesized from 2-mercapto-4-(1-H-indole-2-y1)-6-oxo-1,6-dihydropyriinidine-5-carbonitrile 1 upon nucleophilic attack by the hydrazine hydrate. Compound 1 was synthesized by modified Biginelli condensation method using indole-3-carbaldehyde, ethyl cyanoacetate and thiourea. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and antimicrobial actions. Among the newer derivatives, one compound i.e., 6-(1-H-indole-2-y1)-4-oxo-242-(2,6-dichlorobenzylidene)hydraziny11-4,5-dihydropyrimidine-5-carbonitrile (7) emerged as lead compound having 71.14% inhibition of edema and 12.5 mu g/mL MIC against both bacterial and fungal strains.

• 出版日期2012-12