An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking

A facile, convenient and one-pot three-component method has been outlined for the synthesis of title compounds by treating equimolar amounts of 3-(2-bromoacetyl)-2H-chromen-2-one (2) with 2-cyanothioacetamide (3) and various aryl/heteryl aldehydes (5 or 7) independently. The effect of solvent and ca...

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Main Authors:	Kotthireddy Kavitha, Devulapally Srikrishna, Pasula Aparna
Format:	Article
Language:	English
Published:	Elsevier 2019-03-01
Series:	Journal of Saudi Chemical Society
Online Access:	http://www.sciencedirect.com/science/article/pii/S1319610318300929

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spelling	doaj-3244c805a1c24bd99b69387cb17269372020-11-24T22:05:11ZengElsevierJournal of Saudi Chemical Society1319-61032019-03-01233325337An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular dockingKotthireddy Kavitha0Devulapally Srikrishna1Pasula Aparna2Corresponding author.; Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad College of Engineering, Kukatpally, Hyderabad, Telangana 500 085, IndiaDepartment of Chemistry, Jawaharlal Nehru Technological University, Hyderabad College of Engineering, Kukatpally, Hyderabad, Telangana 500 085, IndiaDepartment of Chemistry, Jawaharlal Nehru Technological University, Hyderabad College of Engineering, Kukatpally, Hyderabad, Telangana 500 085, IndiaA facile, convenient and one-pot three-component method has been outlined for the synthesis of title compounds by treating equimolar amounts of 3-(2-bromoacetyl)-2H-chromen-2-one (2) with 2-cyanothioacetamide (3) and various aryl/heteryl aldehydes (5 or 7) independently. The effect of solvent and catalyst on this one-pot reaction has been studied and the use of l-proline in ethanol was found to be effective to achieve the target compounds (6 & 8) in fair yields. These synthesized compounds were further assessed for the anti-hepatoma activity, and their action mechanism was also investigated by using molecular docking studies. All the compounds 6(a-h) & 8(a-f) manifested excellent potency for anti-hepatoma activity. It should be noted that, compounds 6e, 6f have exhibited almost equipotent activity with reference to standard drug Nexavar. Keywords: One-pot three-component reaction, l-Proline, Eco-friendly method, Molecular docking, Anti-hepatoma studieshttp://www.sciencedirect.com/science/article/pii/S1319610318300929
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Kotthireddy Kavitha Devulapally Srikrishna Pasula Aparna
spellingShingle	Kotthireddy Kavitha Devulapally Srikrishna Pasula Aparna An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking Journal of Saudi Chemical Society
author_facet	Kotthireddy Kavitha Devulapally Srikrishna Pasula Aparna
author_sort	Kotthireddy Kavitha
title	An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
title_short	An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
title_full	An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
title_fullStr	An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
title_full_unstemmed	An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
title_sort	efficient one-pot three-component synthesis of 2-(4-(2-oxo-2h-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking
publisher	Elsevier
series	Journal of Saudi Chemical Society
issn	1319-6103
publishDate	2019-03-01
description	A facile, convenient and one-pot three-component method has been outlined for the synthesis of title compounds by treating equimolar amounts of 3-(2-bromoacetyl)-2H-chromen-2-one (2) with 2-cyanothioacetamide (3) and various aryl/heteryl aldehydes (5 or 7) independently. The effect of solvent and catalyst on this one-pot reaction has been studied and the use of l-proline in ethanol was found to be effective to achieve the target compounds (6 & 8) in fair yields. These synthesized compounds were further assessed for the anti-hepatoma activity, and their action mechanism was also investigated by using molecular docking studies. All the compounds 6(a-h) & 8(a-f) manifested excellent potency for anti-hepatoma activity. It should be noted that, compounds 6e, 6f have exhibited almost equipotent activity with reference to standard drug Nexavar. Keywords: One-pot three-component reaction, l-Proline, Eco-friendly method, Molecular docking, Anti-hepatoma studies
url	http://www.sciencedirect.com/science/article/pii/S1319610318300929
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An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking

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