Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study

Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study

Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latt...

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Main Authors: Tebogo Ankie Khoza, Tshepiso Jan Makhafola, Malose Jack Mphahlele
Format: Article
Language:English
Published: MDPI AG 2015-12-01
Series:Molecules
Subjects:
dihalogenated 2H-imidazo[1,2-c]quinazolines
cross-coupling
imidazo[1,2-c]quinazolines
cytotoxicity
Online Access:http://www.mdpi.com/1420-3049/20/12/19863
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spelling doaj-2bad0cc29fd648bbb191dd53f3fc6a0d2020-11-25T00:52:20ZengMDPI AGMolecules1420-30492015-12-012012225202253310.3390/molecules201219863molecules201219863Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity StudyTebogo Ankie Khoza0Tshepiso Jan Makhafola1Malose Jack Mphahlele2Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P. O. Box 392, Pretoria 0003, South AfricaDepartment of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, University of South Africa, Private Bag X06, FL 1710, South AfricaDepartment of Chemistry, College of Science, Engineering and Technology, University of South Africa, P. O. Box 392, Pretoria 0003, South AfricaAmination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely functionalized polycarbo-substituted 2H-imidazo[1,2-c]quinazolines. The imidazoquinazolines were screened for in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cells and human cervical cancer (HeLa) cells.http://www.mdpi.com/1420-3049/20/12/19863dihalogenated 2H-imidazo[1,2-c]quinazolinescross-couplingimidazo[1,2-c]quinazolinescytotoxicity
collection DOAJ
language English
format Article
sources DOAJ
author Tebogo Ankie Khoza
Tshepiso Jan Makhafola
Malose Jack Mphahlele
spellingShingle Tebogo Ankie Khoza
Tshepiso Jan Makhafola
Malose Jack Mphahlele
Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
Molecules
dihalogenated 2H-imidazo[1,2-c]quinazolines
cross-coupling
imidazo[1,2-c]quinazolines
cytotoxicity
author_facet Tebogo Ankie Khoza
Tshepiso Jan Makhafola
Malose Jack Mphahlele
author_sort Tebogo Ankie Khoza
title Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
title_short Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
title_full Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
title_fullStr Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
title_full_unstemmed Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
title_sort novel polycarbo-substituted imidazo[1,2-c]quinazolines: synthesis and cytotoxicity study
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2015-12-01
description Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely functionalized polycarbo-substituted 2H-imidazo[1,2-c]quinazolines. The imidazoquinazolines were screened for in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cells and human cervical cancer (HeLa) cells.
topic dihalogenated 2H-imidazo[1,2-c]quinazolines
cross-coupling
imidazo[1,2-c]quinazolines
cytotoxicity
url http://www.mdpi.com/1420-3049/20/12/19863
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AT tshepisojanmakhafola novelpolycarbosubstitutedimidazo12cquinazolinessynthesisandcytotoxicitystudy
AT malosejackmphahlele novelpolycarbosubstitutedimidazo12cquinazolinessynthesisandcytotoxicitystudy
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