<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml">The series of 6,7,8,9-tetrahydro-5<italic>H</italic>-5-(2'-hydroxyphenyl)-2-(4'-substituted benzylidine)thiazolo(2,3-<italic>b</italic>)quinazolin-3(2<italic>H</italic>)-ones (<bold>4a-j</bold>) and 6,7,8,9-tetrahydro-5<italic>H</italic>-5-(2'-hydroxyphenyl)-2-(4'-substituted benzylidine)-3-(4-nitrophenyl amino)thiazoloquinazolines (<bold>5a-j</bold>) 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-5<italic>H</italic>-5-(2'-hydroxyphenyl)-2-(4'-fluorobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (<bold>5e</bold>), 6,7,8,9-tetrahydro-5<italic>H</italic>-5-(2'-hydroxyphenyl)-2-(4'-nitrobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (<bold>5j</bold>) and 6,7,8,9-tetrahydro-5<italic>H</italic>-5-(2'-hydroxyphenyl)-2-(4'-chlorobenzylidine)-3-(4-nitrophenylamino)thiazoloquinazoline (<bold>5f</bold>) were found to be more potent than theophylline (<italic>IC</italic>50 in mmol L-1 of 1.34 ± 0.09 for <bold>5f</bold>, 1.44 ± 0.02 for <bold>5e</bold>, 1.52 ± 0.05 for <bold>5j</bold><italic>vs.</italic> 1.72 ± 0.09 for theophylline).</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-nitrophenyl amino)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 5jvs. 1.72 ± 0.09 for theophylline).

Synthesis and cAMP-dependent phosphodiesterase inhibition of novel thiazoloquinazoline derivatives

Department of Biotechnology, Acharya Nagarjuna University, Guntur-522510, India

Department of Pharmacy, College Sadaya, International University, Jalan Menara Gading 56000 Cheras Kuala Lumpur, Malaysia

Acta Pharmaceutica

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...

Synthesis and cAMP-dependent phosphodiesterase inhibition of novel thiazoloquinazoline derivatives

Pubblicato online: 15 mar 2011

Pagine: 103 - 113

DOI: https://doi.org/10.2478/v10007-011-0009-3

Parole chiave
tiazolokinazolin, benzilidinetiazolokinazolin, nitrofenilaminotiazolokinazolin, inhibicija fosfodiesteraze, SAR

This content is open access.

Synthesis and cAMP-dependent phosphodiesterase inhibition of novel thiazoloquinazoline derivatives

Pubblicato online: 15 mar 2011

Pagine: 103 - 113

DOI: https://doi.org/10.2478/v10007-011-0009-3

Parole chiavetiazolokinazolin, benzilidinetiazolokinazolin, nitrofenilaminotiazolokinazolin, inhibicija fosfodiesteraze, SAR

This content is open access.

Parole chiave
tiazolokinazolin, benzilidinetiazolokinazolin, nitrofenilaminotiazolokinazolin, inhibicija fosfodiesteraze, SAR