Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies

A series of chalcone analogues (1–15) were synthesized by Claisen-Schmidt condensation in good yields (70–95%) and characterized by FT-IR, 1H NMR and mass spectral methods. Additionally, compounds 3 and 7 were characterized by 13C NMR. Antitubercular and antioxidant activities of the chalcones were...

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Autores principales:	Shaik Ammaji, Shaik Masthanamma, Richie R. Bhandare, Sivakumar Annadurai, Afzal Basha Shaik
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2022
Materias:	Hydroxy chalcones Chlorinated chalcones Antitubercular activity Antioxidant activity Autodock SwissADME Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/33fe2407f34c41bcb172add7a8cacff7
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spelling	oai:doaj.org-article:33fe2407f34c41bcb172add7a8cacff72021-12-04T04:33:30ZAntitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies1878-535210.1016/j.arabjc.2021.103581https://doaj.org/article/33fe2407f34c41bcb172add7a8cacff72022-02-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1878535221005967https://doaj.org/toc/1878-5352A series of chalcone analogues (1–15) were synthesized by Claisen-Schmidt condensation in good yields (70–95%) and characterized by FT-IR, 1H NMR and mass spectral methods. Additionally, compounds 3 and 7 were characterized by 13C NMR. Antitubercular and antioxidant activities of the chalcones were evaluated by MABA and DPPH free radical assays. In MABA assay analogues 3 (MIC = 14 ± 0.11 µM) and 11 (MIC = 14 ± 0.17 µM) bearing fluorine and methoxy groups at para and meta positions were 1.8-times more active than the standard pyrazinamide (MIC = 25.34 ± 0.22 µM). The chalcone analogues such as compound 7 (IC50 = 4 ± 1 µg/mL) containing electron releasing groups such as OH at ortho position had slightly more antioxidant activity than Gallic acid (IC50 = 5 ± 1 µg/mL). The potential compounds 3, 7, 9 and 11 were less selective and toxic against human live cell lines-LO2. Further, molecular docking results of chalcones against anti-tubercular drug target isocitrate lyase (PDB ID: 1F8M) revealed that compound 3 and 11 shown least binding energies as −7.6, and −7.5 kcal/mol are in line with in vitro MABA assay, suggesting that these compounds 3 and 11 are strong inhibitor of isocitrate lyase. SwissADME programme estimated the drug likeliness properties of compounds 3, 7, 9 and 11. The lead molecules arisen through this study helps to develop new antitubercular and antioxidant agents.Shaik AmmajiShaik MasthanammaRichie R. BhandareSivakumar AnnaduraiAfzal Basha ShaikElsevierarticleHydroxy chalconesChlorinated chalconesAntitubercular activityAntioxidant activityAutodockSwissADMEChemistryQD1-999ENArabian Journal of Chemistry, Vol 15, Iss 2, Pp 103581- (2022)
institution	DOAJ
collection	DOAJ
language	EN
topic	Hydroxy chalcones Chlorinated chalcones Antitubercular activity Antioxidant activity Autodock SwissADME Chemistry QD1-999
spellingShingle	Hydroxy chalcones Chlorinated chalcones Antitubercular activity Antioxidant activity Autodock SwissADME Chemistry QD1-999 Shaik Ammaji Shaik Masthanamma Richie R. Bhandare Sivakumar Annadurai Afzal Basha Shaik Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
description	A series of chalcone analogues (1–15) were synthesized by Claisen-Schmidt condensation in good yields (70–95%) and characterized by FT-IR, 1H NMR and mass spectral methods. Additionally, compounds 3 and 7 were characterized by 13C NMR. Antitubercular and antioxidant activities of the chalcones were evaluated by MABA and DPPH free radical assays. In MABA assay analogues 3 (MIC = 14 ± 0.11 µM) and 11 (MIC = 14 ± 0.17 µM) bearing fluorine and methoxy groups at para and meta positions were 1.8-times more active than the standard pyrazinamide (MIC = 25.34 ± 0.22 µM). The chalcone analogues such as compound 7 (IC50 = 4 ± 1 µg/mL) containing electron releasing groups such as OH at ortho position had slightly more antioxidant activity than Gallic acid (IC50 = 5 ± 1 µg/mL). The potential compounds 3, 7, 9 and 11 were less selective and toxic against human live cell lines-LO2. Further, molecular docking results of chalcones against anti-tubercular drug target isocitrate lyase (PDB ID: 1F8M) revealed that compound 3 and 11 shown least binding energies as −7.6, and −7.5 kcal/mol are in line with in vitro MABA assay, suggesting that these compounds 3 and 11 are strong inhibitor of isocitrate lyase. SwissADME programme estimated the drug likeliness properties of compounds 3, 7, 9 and 11. The lead molecules arisen through this study helps to develop new antitubercular and antioxidant agents.
format	article
author	Shaik Ammaji Shaik Masthanamma Richie R. Bhandare Sivakumar Annadurai Afzal Basha Shaik
author_facet	Shaik Ammaji Shaik Masthanamma Richie R. Bhandare Sivakumar Annadurai Afzal Basha Shaik
author_sort	Shaik Ammaji
title	Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
title_short	Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
title_full	Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
title_fullStr	Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
title_full_unstemmed	Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies
title_sort	antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: synthesis, biological and computational studies
publisher	Elsevier
publishDate	2022
url	https://doaj.org/article/33fe2407f34c41bcb172add7a8cacff7
work_keys_str_mv	AT shaikammaji antitubercularandantioxidantactivitiesofhydroxyandchlorosubstitutedchalconeanaloguessynthesisbiologicalandcomputationalstudies AT shaikmasthanamma antitubercularandantioxidantactivitiesofhydroxyandchlorosubstitutedchalconeanaloguessynthesisbiologicalandcomputationalstudies AT richierbhandare antitubercularandantioxidantactivitiesofhydroxyandchlorosubstitutedchalconeanaloguessynthesisbiologicalandcomputationalstudies AT sivakumarannadurai antitubercularandantioxidantactivitiesofhydroxyandchlorosubstitutedchalconeanaloguessynthesisbiologicalandcomputationalstudies AT afzalbashashaik antitubercularandantioxidantactivitiesofhydroxyandchlorosubstitutedchalconeanaloguessynthesisbiologicalandcomputationalstudies
_version_	1718372961140867072

Antitubercular and antioxidant activities of hydroxy and chloro substituted chalcone analogues: Synthesis, biological and computational studies

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