Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential

Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential

A simple, efficient and eco-friendly method for the synthesis of 1,2-dihydroquinazolines has been developed using three-component reaction of readily available aromatic aldehydes, 2-aminobenzophenones, ammonium acetate with sulfamic acid as a green and recyclable catalyst. The significant features o...

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Main Authors: Ahmed Kamal, Korrapati Suresh Babu, Y. Poornachandra, Burri Nagaraju, S.M. Ali Hussaini, Siddiq Pasha Shaik, C. Ganesh Kumar, Abdullah Alarifi
Format: Article
Language:English
Published: Elsevier 2019-12-01
Series:Arabian Journal of Chemistry
Online Access:http://www.sciencedirect.com/science/article/pii/S1878535215003093
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spelling doaj-08c76981c9dc4c0dae49e18be4f8d98f2020-11-25T02:22:43ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112835463554Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potentialAhmed Kamal0Korrapati Suresh Babu1Y. Poornachandra2Burri Nagaraju3S.M. Ali Hussaini4Siddiq Pasha Shaik5C. Ganesh Kumar6Abdullah Alarifi7Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Catalytic Chemistry Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia; Corresponding author at: Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India. Tel.: +91 40 27193157; fax: +91 40 27193189.Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaMedicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaMedicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaMedicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaMedicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaMedicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaCatalytic Chemistry Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi ArabiaA simple, efficient and eco-friendly method for the synthesis of 1,2-dihydroquinazolines has been developed using three-component reaction of readily available aromatic aldehydes, 2-aminobenzophenones, ammonium acetate with sulfamic acid as a green and recyclable catalyst. The significant features of this method include short reaction time, operational simplicity, high yields and high selectivity. Interestingly, the catalyst can be recovered and reused for up to four cycles without any loss in catalytic activity. By employing this method, a series of 23 compounds was synthesized and tested for antimicrobial activity against both Gram-positive and Gram-negative bacterial strains as well as a fungal strain. Among these, compounds 4l, 4v and 4w showed appreciable antibacterial activity selectively against Gram-positive bacteria, wherein compound 4w exhibited promising antibacterial activity with MIC value of 0.010 μMol L−1 against Staphylococcus aureus MTCC 96 and Micrococcus luteus MTCC 2470. In addition, 4w also showed promising bactericidal and biofilm formation inhibitory effects. Keywords: 1,2-Dihydroquinazolines, Sulfamic acid, Recyclability, Antimicrobial, Anti-biofilmhttp://www.sciencedirect.com/science/article/pii/S1878535215003093
collection DOAJ
language English
format Article
sources DOAJ
author Ahmed Kamal
Korrapati Suresh Babu
Y. Poornachandra
Burri Nagaraju
S.M. Ali Hussaini
Siddiq Pasha Shaik
C. Ganesh Kumar
Abdullah Alarifi
spellingShingle Ahmed Kamal
Korrapati Suresh Babu
Y. Poornachandra
Burri Nagaraju
S.M. Ali Hussaini
Siddiq Pasha Shaik
C. Ganesh Kumar
Abdullah Alarifi
Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
Arabian Journal of Chemistry
author_facet Ahmed Kamal
Korrapati Suresh Babu
Y. Poornachandra
Burri Nagaraju
S.M. Ali Hussaini
Siddiq Pasha Shaik
C. Ganesh Kumar
Abdullah Alarifi
author_sort Ahmed Kamal
title Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
title_short Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
title_full Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
title_fullStr Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
title_full_unstemmed Efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
title_sort efficient and green sulfamic acid catalyzed synthesis of new 1,2-dihydroquinazoline derivatives with antibacterial potential
publisher Elsevier
series Arabian Journal of Chemistry
issn 1878-5352
publishDate 2019-12-01
description A simple, efficient and eco-friendly method for the synthesis of 1,2-dihydroquinazolines has been developed using three-component reaction of readily available aromatic aldehydes, 2-aminobenzophenones, ammonium acetate with sulfamic acid as a green and recyclable catalyst. The significant features of this method include short reaction time, operational simplicity, high yields and high selectivity. Interestingly, the catalyst can be recovered and reused for up to four cycles without any loss in catalytic activity. By employing this method, a series of 23 compounds was synthesized and tested for antimicrobial activity against both Gram-positive and Gram-negative bacterial strains as well as a fungal strain. Among these, compounds 4l, 4v and 4w showed appreciable antibacterial activity selectively against Gram-positive bacteria, wherein compound 4w exhibited promising antibacterial activity with MIC value of 0.010 μMol L−1 against Staphylococcus aureus MTCC 96 and Micrococcus luteus MTCC 2470. In addition, 4w also showed promising bactericidal and biofilm formation inhibitory effects. Keywords: 1,2-Dihydroquinazolines, Sulfamic acid, Recyclability, Antimicrobial, Anti-biofilm
url http://www.sciencedirect.com/science/article/pii/S1878535215003093
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