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A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

BACKGROUND: Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. RESULTS: 4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-me...

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Autores principales: Gomha, Sobhi M., Abdelaziz, Mohamad R., Kheder, Nabila A., Abdel-aziz, Hassan M., Alterary, Seham, Mabkhot, Yahia N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5643583/
https://www.ncbi.nlm.nih.gov/pubmed/29086869
http://dx.doi.org/10.1186/s13065-017-0335-8
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author Gomha, Sobhi M.
Abdelaziz, Mohamad R.
Kheder, Nabila A.
Abdel-aziz, Hassan M.
Alterary, Seham
Mabkhot, Yahia N.
author_facet Gomha, Sobhi M.
Abdelaziz, Mohamad R.
Kheder, Nabila A.
Abdel-aziz, Hassan M.
Alterary, Seham
Mabkhot, Yahia N.
author_sort Gomha, Sobhi M.
collection PubMed
description BACKGROUND: Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. RESULTS: 4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)-N′-phenylpropane hydrazonoyl chlorides 5a–c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a–c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC(50) = 1.61 ± 1.92 (μg/mL)) and 11 (IC(50) = 1.98 ± 1.22 (μg/mL)). The structure–activity relationships have been suggested based on their anticancer results. CONCLUSIONS: A novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents. [Image: see text]
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spelling pubmed-56435832017-10-30 A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents Gomha, Sobhi M. Abdelaziz, Mohamad R. Kheder, Nabila A. Abdel-aziz, Hassan M. Alterary, Seham Mabkhot, Yahia N. Chem Cent J Research Article BACKGROUND: Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. RESULTS: 4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)-N′-phenylpropane hydrazonoyl chlorides 5a–c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a–c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC(50) = 1.61 ± 1.92 (μg/mL)) and 11 (IC(50) = 1.98 ± 1.22 (μg/mL)). The structure–activity relationships have been suggested based on their anticancer results. CONCLUSIONS: A novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents. [Image: see text] Springer International Publishing 2017-10-16 /pmc/articles/PMC5643583/ /pubmed/29086869 http://dx.doi.org/10.1186/s13065-017-0335-8 Text en © The Author(s) 2017 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Gomha, Sobhi M.
Abdelaziz, Mohamad R.
Kheder, Nabila A.
Abdel-aziz, Hassan M.
Alterary, Seham
Mabkhot, Yahia N.
A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title_full A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title_fullStr A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title_full_unstemmed A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title_short A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
title_sort facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5643583/
https://www.ncbi.nlm.nih.gov/pubmed/29086869
http://dx.doi.org/10.1186/s13065-017-0335-8
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