Synthesis and antiviral activity of new 3-methyl-1,5-diphenyl-1H-pyrazole derivatives

A new series of 4-substituted 3-methyl-1,5-diphenyl-1 H -pyrazoles 4 – 11 has been synthesized and evaluated for its in vitro antiviral activity and cytotoxicity against herpes simplex virus type-1 grown on Vero African green monkey kidney cells through plaque-reduction assay method using acyclovir...

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Published inMedicinal chemistry research Vol. 21; no. 12; pp. 4139 - 4149
Main Authors Tantawy, Atif S., Nasr, Magda N. A., El-Sayed, Magda A. A., Tawfik, Samar S.
Format Journal Article
LanguageEnglish
Published New York Springer-Verlag 01.12.2012
Subjects
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
Plaque reduction
Pyridine
Pyrazoles
Antiviral activity
Pyrazolines
Isoxazoline
Pyrimidine
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Summary:A new series of 4-substituted 3-methyl-1,5-diphenyl-1 H -pyrazoles 4 – 11 has been synthesized and evaluated for its in vitro antiviral activity and cytotoxicity against herpes simplex virus type-1 grown on Vero African green monkey kidney cells through plaque-reduction assay method using acyclovir as a positive control. The synthesis was achieved through Claisen-Schmidt condensation reaction of 3-methyl-1,5-diphenyl-1 H -pyrazole-4-carbaldehyde ( 3 ) with acetophenone derivatives to give various enones 4a – f which are considered an important synthon for the construction of different heterocyclic rings as isoxazoline, pyrazoline, pyrimidine, pyridine, and fused pyridine via several synthetic routes. Biological evaluation of the prepared compounds showed that 3-(4-methylphenyl)-5-(3-methyl-1,5-diphenyl-1 H -pyrazol-4-yl)-4,5-dihydroisoxazole ( 5f ), 6-(4-methylphenyl)- N -[(3-(methylsulfanyl)phenyl)]-4-(3-methyl-1,5-diphenyl-1 H -pyrazol-4-yl)pyrimidin-2-amine ( 7 ), 6-(4-bromophenyl)-4-(3-methyl-1,5-diphenyl-1 H -pyrazol-4-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile ( 8 ), and 2-amino-6-(4-bromophenyl)-4-(3-methyl-1,5-diphenyl-1 H -pyrazol-4-yl) pyridine-3-carbonitrile ( 9 ) exhibited strong antiviral activity with IC 50 (0.02, 0.04, 0.03, 0.03), respectively, compared to the used reference drug. The synthesized compounds were characterized by physical constants and the structures of the title compounds were confirmed by IR, 1 H NMR, mass spectra, and elemental analyses.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-011-9960-2