Acta Pharmaceutica, Vol. 61 No. 1, 2011.
Short communication, Note
https://doi.org/10.2478/v10007-011-0009-3
Synthesis and cAMP-dependent phosphodiesterase inhibition activity of novel thiazoloquinazoline derivatives
THEIVENDREN PANNEER SELVAM
orcid.org/0000-0002-8197-4688
; Department of Biotechnology, Acharya Nagarjuna University, Guntur-522510, India
PALANIRAJAN VIJAYARAJ KUMAR
; Department of Pharmacy, College Sadaya, International University, Jalan Menara Gading 56000 Cheras, Kuala Lumpur, Malaysia
Abstract
The series of 6,7,8,9-tetrahydro-5H-5-(2'-hydroxyphenyl)-2-(4'-substituted benzylidine) thiazolo(2,3-b)quinazolin-3(2H)-ones (4a-j) and 6,7,8,9-tetrahydro-5H-5-(2'-hydroxyphenyl)-2-(4'-substituted benzylidine)-3-(4-nitrophenylamino)thiazoloquinazolines (5a-j) were synthesized by the reported method and evaluated for their phosphodiesterase inhibitory activity. All test compounds exhibited good activity. The structure-activity relationships were also studied. In both series of compounds, electron-withdrawing substitutions showed higher activity. Among the tested compounds, 6,7,8,9-tetrahydro-5H-5-(2'-hydroxyphenyl)-2-(4'-fluorobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (5e), 6,7,8,9-tetrahydro-5H-5-(2'-hydroxyphenyl)-2-(4'-nitrobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (5j) and 6,7,8,9-tetrahydro-5H-5-(2'-hydroxyphenyl)-2-(4'-chlorobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (5f) were found to be more potent than theophylline (IC50 in mmol L–1 of 1.34 ± 0.09 for 5f, 1.44 ± 0.02 for 5e, 1.52 ± 0.05 for 5j vs. 1.72 ± 0.09 for theophylline).
Keywords
thiazoloquinazoline; benzylidinethiazoloquinazoline; nitrophenylaminothiazolo quinazoline; phosphodiesterase inhibition; SAR
Hrčak ID:
63380
URI
Publication date:
1.3.2011.
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