Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-l-carboxylate derivatives

Nayak, B.; Ciftci-Yabanoglu, S.; Jadav, Surender; Jagrat, Monika; Sinha, Barij; UÇAR, GÜLBERK; Jayaprakash, Venkatesan

doi:10.1016/j.ejmech.2013.09.010

Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-l-carboxylate derivatives

Nayak B. V., Ciftci-Yabanoglu S., Jadav S. S., Jagrat M., Sinha B. N., UÇAR G., ...Daha Fazla

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.69, ss.762-767, 2013 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 69
Basım Tarihi: 2013
Doi Numarası: 10.1016/j.ejmech.2013.09.010
Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.762-767
Hacettepe Üniversitesi Adresli: Evet

Özet

Ethyl and phenyl carbamate derivatives of pyrazoline (3a-3h) were synthesized and tested for their MAO inhibitory activity. All the compounds were found to be selective towards MAO-A. Phenyl carbamates (3e-3h) were better than ethyl carbamates (3a-3d) and displayed the best selectivity index. Compound 3f (Ki(MAO-A); 4.96 +/- 0.21 nM) was found to be equally potent as that of standard drug, Moclobemide (Ki(MAO-A); 5.01 +/- 0.13 nM) but with best selectivity index (8.86 x 10-5). Molecular docking studies with R & S conformer of 3f revealed S-enantiomer is better than R-enantiomer as reported earlier by other groups. It is proposed that VdW's radii of the substitution (bulkiness) in ring B determine the potency of phenyl carbamates. (C) 2013 Elsevier Masson SAS. All rights reserved.