Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent

Due to their role in cell growth and survival, HDAC (II), JAK 2 and EGFR receptors are important targets in many chemotherapies that aim to produce their biological response in malignancy solid tumors. In this work, several 4-hydroxybenzamide analogues coupled with 1,3-benzodioxole, a,ß-unsaturated...

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Autores principales:	Chia Hui Low, Habsah Mohamad, Siti Fatimah Zaharah Mustafa, Khamsah Suryati Mohd, Nor Elani Mat Nafi
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2022
Materias:	Benzamide analogues Histone deacetylase II (HDAC II) enzymes Janus kinase (JAK2) enzymes Epidermal growth factor receptor (EGFR) Cytotoxic Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/182e3f267666411a9cef620cc101cd8f
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id	oai:doaj.org-article:182e3f267666411a9cef620cc101cd8f
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spelling	oai:doaj.org-article:182e3f267666411a9cef620cc101cd8f2021-11-14T04:31:26ZSynthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent1878-535210.1016/j.arabjc.2021.103510https://doaj.org/article/182e3f267666411a9cef620cc101cd8f2022-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1878535221005256https://doaj.org/toc/1878-5352Due to their role in cell growth and survival, HDAC (II), JAK 2 and EGFR receptors are important targets in many chemotherapies that aim to produce their biological response in malignancy solid tumors. In this work, several 4-hydroxybenzamide analogues coupled with 1,3-benzodioxole, a,ß-unsaturated carbonyl, and tert-butyl ester bases small molecules were synthesized via imidation, EDC coupling, and etherification reactions, then bio-active 4-hydroxybenzamide analogues were studied using quantum calculations and molecular docking. The Frontier molecular orbitals and energy gap values were calculated using Time-Dependent Density Functional Theory (TD-DFT). Docking results showed A and E as potent JAK2 inhibitors. B, C, and F may be good HDAC II inhibitors. D may act as a potent EGFR inhibitor. These were followed by cytotoxic evaluation of 4-hydroxybenzamide analogues on human estrogen receptor breast cancer cells (MCF-7), metastatic breast adenocarcinome cancer cells (MDA-MB-231), and fibroblast cells (NIH/3T3) respectively. Molecule E was found to have insignificant apoptosis against MCF 7 cell line and MDM-MD-231 cell lines with IC50 value 5.0 µg⁄mL and 5.0 µg⁄mL respectively.Chia Hui LowHabsah MohamadSiti Fatimah Zaharah MustafaKhamsah Suryati MohdNor Elani Mat NafiElsevierarticleBenzamide analoguesHistone deacetylase II (HDAC II) enzymesJanus kinase (JAK2) enzymesEpidermal growth factor receptor (EGFR)CytotoxicChemistryQD1-999ENArabian Journal of Chemistry, Vol 15, Iss 1, Pp 103510- (2022)
institution	DOAJ
collection	DOAJ
language	EN
topic	Benzamide analogues Histone deacetylase II (HDAC II) enzymes Janus kinase (JAK2) enzymes Epidermal growth factor receptor (EGFR) Cytotoxic Chemistry QD1-999
spellingShingle	Benzamide analogues Histone deacetylase II (HDAC II) enzymes Janus kinase (JAK2) enzymes Epidermal growth factor receptor (EGFR) Cytotoxic Chemistry QD1-999 Chia Hui Low Habsah Mohamad Siti Fatimah Zaharah Mustafa Khamsah Suryati Mohd Nor Elani Mat Nafi Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
description	Due to their role in cell growth and survival, HDAC (II), JAK 2 and EGFR receptors are important targets in many chemotherapies that aim to produce their biological response in malignancy solid tumors. In this work, several 4-hydroxybenzamide analogues coupled with 1,3-benzodioxole, a,ß-unsaturated carbonyl, and tert-butyl ester bases small molecules were synthesized via imidation, EDC coupling, and etherification reactions, then bio-active 4-hydroxybenzamide analogues were studied using quantum calculations and molecular docking. The Frontier molecular orbitals and energy gap values were calculated using Time-Dependent Density Functional Theory (TD-DFT). Docking results showed A and E as potent JAK2 inhibitors. B, C, and F may be good HDAC II inhibitors. D may act as a potent EGFR inhibitor. These were followed by cytotoxic evaluation of 4-hydroxybenzamide analogues on human estrogen receptor breast cancer cells (MCF-7), metastatic breast adenocarcinome cancer cells (MDA-MB-231), and fibroblast cells (NIH/3T3) respectively. Molecule E was found to have insignificant apoptosis against MCF 7 cell line and MDM-MD-231 cell lines with IC50 value 5.0 µg⁄mL and 5.0 µg⁄mL respectively.
format	article
author	Chia Hui Low Habsah Mohamad Siti Fatimah Zaharah Mustafa Khamsah Suryati Mohd Nor Elani Mat Nafi
author_facet	Chia Hui Low Habsah Mohamad Siti Fatimah Zaharah Mustafa Khamsah Suryati Mohd Nor Elani Mat Nafi
author_sort	Chia Hui Low
title	Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
title_short	Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
title_full	Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
title_fullStr	Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
title_full_unstemmed	Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
title_sort	synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent
publisher	Elsevier
publishDate	2022
url	https://doaj.org/article/182e3f267666411a9cef620cc101cd8f
work_keys_str_mv	AT chiahuilow synthesisandcomputationalstudyof4hydroxylbenzamideanalogousaspotentialantibreastcanceragent AT habsahmohamad synthesisandcomputationalstudyof4hydroxylbenzamideanalogousaspotentialantibreastcanceragent AT sitifatimahzaharahmustafa synthesisandcomputationalstudyof4hydroxylbenzamideanalogousaspotentialantibreastcanceragent AT khamsahsuryatimohd synthesisandcomputationalstudyof4hydroxylbenzamideanalogousaspotentialantibreastcanceragent AT norelanimatnafi synthesisandcomputationalstudyof4hydroxylbenzamideanalogousaspotentialantibreastcanceragent
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Synthesis and computational study of 4-hydroxylbenzamide analogous as potential anti-breast cancer agent

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