Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons
New ecofriendly Biginelli reaction procedures have been adapted to prepare new dihydropyrimidines (DHPMs) using a multicomponent one-pot reaction. All the synthesized compounds were evaluated for their anticancer activity against 59 human cancer cell lines and evaluated for their antimicrobial activ...
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doaj-d3fd91cfbf8a40a58539e04e9c07146e2021-06-11T09:33:07ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922021-04-0114222123310.1080/17518253.2021.18967891896789Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthonsAfaf El-Malah0Zeinab Mahmoud1Heba Hamed Salem2Amr M. Abdou3Mona M. H. Soliman4Rasha A. Hassan5Cairo UniversityCairo UniversityKing Khalid UniversityNational Research CentreNational Research CentreCairo UniversityNew ecofriendly Biginelli reaction procedures have been adapted to prepare new dihydropyrimidines (DHPMs) using a multicomponent one-pot reaction. All the synthesized compounds were evaluated for their anticancer activity against 59 human cancer cell lines and evaluated for their antimicrobial activities against representatives of both Gram-positive and Gram-negative bacteria. Compound 4 showed marked wide spectrum anticancer activity towards most of the tested cancer cell lines with a percentage of growth inhibition of 29.04–71.68% against leukemia cell line (K-562 and SR), lung cancer cell line (NCI-H522), five colon cancer cell lines (HCT-116, HCT-15, HT29, KM12 and SW-620), CNS cancer cell line (SF-295 and SNB-75), melanoma cell lines (MALME-3M and M14), renal cancer cell line (CAKI-1) and breast cancer cell lines (MCF7 and MDA-MB-468). The highest observed anticancer activity was against leukemia cell lines K-562 and SR with inhibition percentages of 64.97 and 71.68%, respectively. The renal cancer cell line (UO-31) was particularly sensitive towards all the evaluated compounds. Compounds including 2b and 5c exhibited antibacterial activity against S. aureus while 2a and 5b exhibited antifungal activity against C. albicans. The results also showed that compounds 2c and 5e exhibited both antibacterial and antifungal activity against S. aureus and C. albicans respectively.http://dx.doi.org/10.1080/17518253.2021.18967892-thioxo-1,2,3,6-tetrahydropyrimidine 4-carboxylate estersbiginelli reactionβ-aroylpyruvatesanticancer activityantimicrobial activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Afaf El-Malah Zeinab Mahmoud Heba Hamed Salem Amr M. Abdou Mona M. H. Soliman Rasha A. Hassan |
spellingShingle |
Afaf El-Malah Zeinab Mahmoud Heba Hamed Salem Amr M. Abdou Mona M. H. Soliman Rasha A. Hassan Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons Green Chemistry Letters and Reviews 2-thioxo-1,2,3,6-tetrahydropyrimidine 4-carboxylate esters biginelli reaction β-aroylpyruvates anticancer activity antimicrobial activity |
author_facet |
Afaf El-Malah Zeinab Mahmoud Heba Hamed Salem Amr M. Abdou Mona M. H. Soliman Rasha A. Hassan |
author_sort |
Afaf El-Malah |
title |
Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
title_short |
Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
title_full |
Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
title_fullStr |
Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
title_full_unstemmed |
Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
title_sort |
design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative biginelli dihydropyrimidines using β-aroylpyruvates as synthons |
publisher |
Taylor & Francis Group |
series |
Green Chemistry Letters and Reviews |
issn |
1751-8253 1751-7192 |
publishDate |
2021-04-01 |
description |
New ecofriendly Biginelli reaction procedures have been adapted to prepare new dihydropyrimidines (DHPMs) using a multicomponent one-pot reaction. All the synthesized compounds were evaluated for their anticancer activity against 59 human cancer cell lines and evaluated for their antimicrobial activities against representatives of both Gram-positive and Gram-negative bacteria. Compound 4 showed marked wide spectrum anticancer activity towards most of the tested cancer cell lines with a percentage of growth inhibition of 29.04–71.68% against leukemia cell line (K-562 and SR), lung cancer cell line (NCI-H522), five colon cancer cell lines (HCT-116, HCT-15, HT29, KM12 and SW-620), CNS cancer cell line (SF-295 and SNB-75), melanoma cell lines (MALME-3M and M14), renal cancer cell line (CAKI-1) and breast cancer cell lines (MCF7 and MDA-MB-468). The highest observed anticancer activity was against leukemia cell lines K-562 and SR with inhibition percentages of 64.97 and 71.68%, respectively. The renal cancer cell line (UO-31) was particularly sensitive towards all the evaluated compounds. Compounds including 2b and 5c exhibited antibacterial activity against S. aureus while 2a and 5b exhibited antifungal activity against C. albicans. The results also showed that compounds 2c and 5e exhibited both antibacterial and antifungal activity against S. aureus and C. albicans respectively. |
topic |
2-thioxo-1,2,3,6-tetrahydropyrimidine 4-carboxylate esters biginelli reaction β-aroylpyruvates anticancer activity antimicrobial activity |
url |
http://dx.doi.org/10.1080/17518253.2021.1896789 |
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