title: Anti-inflammatory and antimicrobial activity of 4,5-dihydropyrimidine-5-carbonitrile derivatives: their synthesis and spectral elucidation.
abstract: Thirteen new 6-(1-H-indole-2-yl)-4-oxo-2-[2-(substituted-benzylidene)-hydrazinyl]-4,5-dihydropy-rimidine-5-carbonitrile derivatives were synthesized. The title compounds, hydrazones, were synthesized by reaction of hydrazine group of 2-hydrazinyl-4-(1-H-indole-2-yl)-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-yl)-6-oxo-1,6-dihy-dropyrimidine-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-yl)-4-oxo-2-[2-(2,6-dichlorobenzylidene)-hydrazinyl]-4,5-dihydropyrimidine-5-carbonitrile (7) emerged as lead compound having 71.14% inhibition of edema and 12.5 microg/mL MIC against both bacterial and fungal strains.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi - 110062, India.
authors.forename: Mohammad Mumtaz
authors.initials: MM
authors.lastname: Alam
authors.forename: Mymoona
authors.initials: M
authors.lastname: Akhter
authors.forename: Asif
authors.initials: A
authors.lastname: Husain
authors.forename: Akranth
authors.initials: A
authors.lastname: Marella
authors.forename: Om Prakash
authors.initials: OP
authors.lastname: Tanwar
authors.forename: Rahmat
authors.initials: R
authors.lastname: Ali
authors.forename: Syed Misbahul
authors.initials: SM
authors.lastname: Hasan
authors.forename: Harish
authors.initials: H
authors.lastname: Kumar
authors.forename: Rashiduddin
authors.initials: R
authors.lastname: Haider
authors.forename: Mohammad
authors.initials: M
authors.lastname: Shaquiquzzaman
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005260:Female; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar
chemical_list: D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D007211:Indoles; D011743:Pyrimidines