One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones and their antibacterial evaluation

A series of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones (5a-j) were synthesized by one-pot multicomponent reaction of 6-methoxy-1-tetralone, aryl aldehydes, and thiourea followed by cyclization with 3-(2-bromoacetyl)-2$H$-chromen-2-one in the presence of a Bronsted solid acid catalyst, poly(4-vinylpyridinium)hydrogen sulfate [P(4-VPH)HSO$_{4}$] (0.015 g), under solvent-free conditions at 120 $^{\circ}$C. All the synthesized compounds were characterized by spectral studies and screened for their in vitro antibacterial activity against S. aureus and B. thuringiensis (gram positive), and E. coli and K. pneumoniae (gram negative) bacterial strains. On comparing with the standard drug gentamicin, compounds derived from 4-methoxy and 3,4,5-trimethoxy benzaldehyde, i.e. 5g and 5h, showed broad spectrum antibacterial activity and the remaining compounds showed weak to moderate activity.

One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10- tetrahydro-5H -benzo[h]thiazolo[2,3-b]quinazolin-9-yl)-2H -chromen-2-ones and their antibacterial evaluation

A series of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones (5a-j) were synthesized by one-pot multicomponent reaction of 6-methoxy-1-tetralone, aryl aldehydes, and thiourea followed by cyclization with 3-(2-bromoacetyl)-2$H$-chromen-2-one in the presence of a Bronsted solid acid catalyst, poly(4-vinylpyridinium)hydrogen sulfate [P(4-VPH)HSO$_{4}$] (0.015 g), under solvent-free conditions at 120 $^{\circ}$C. All the synthesized compounds were characterized by spectral studies and screened for their in vitro antibacterial activity against S. aureus and B. thuringiensis (gram positive), and E. coli and K. pneumoniae (gram negative) bacterial strains. On comparing with the standard drug gentamicin, compounds derived from 4-methoxy and 3,4,5-trimethoxy benzaldehyde, i.e. 5g and 5h, showed broad spectrum antibacterial activity and the remaining compounds showed weak to moderate activity.

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Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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Encapsulation of copper(II) complexes with three dentate NO2 ligands derived from 2,6-pyridinedicarboxylic acid in NaY zeolite

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Dinitrogen reduction on a polypyrrole coated Pt electrode under high-pressure conditions: electrochemical impedance spectroscopy studies

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Green synthesis of 2-amino-7-hydroxy-4-aryl-4$H$-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl$_{2}$

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Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates, and bis-triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones

ABDELWAHED SAYED

Synthesis, characterization, biological studies, and molecular modeling of mixed ligand bivalent metal complexes of Schiff bases based on N-aminopyrimidine-2-one/2-thione

Mehmet SÖNMEZ, İsmet BERBER, Feyza YILMAZ, Tuğba TOK TAŞKIN, Hatice Gamze SOĞUKÖMEROĞULLARI

Encapsulation of copper(II) complexes with three dentate NO$_{2}$ ligands derived from 2,6-pyridinedicarboxylic acid in NaY zeolite

MASSOMEH GHORBANLOO, SOMAYEH GHAMARI, HIDENORI YAHIRO