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N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents

A new series of N-(5-Mercapto-1,3,4-thiadiazol-2-yl)-2-phenylacetamide derivatives (3a-3j) were synthesized via an amidation reaction using EDC and HOBt in acetonitrile solvent at room temperature condition. Chemical structures were characterized by (1)H NMR, IR and MS spectroscopic methods and rela...

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Autores principales: Mohammadi-Farani, Ahmad, Heidarian, Neda, Aliabadi, Alireza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4157023/
https://www.ncbi.nlm.nih.gov/pubmed/25237343
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author Mohammadi-Farani, Ahmad
Heidarian, Neda
Aliabadi, Alireza
author_facet Mohammadi-Farani, Ahmad
Heidarian, Neda
Aliabadi, Alireza
author_sort Mohammadi-Farani, Ahmad
collection PubMed
description A new series of N-(5-Mercapto-1,3,4-thiadiazol-2-yl)-2-phenylacetamide derivatives (3a-3j) were synthesized via an amidation reaction using EDC and HOBt in acetonitrile solvent at room temperature condition. Chemical structures were characterized by (1)H NMR, IR and MS spectroscopic methods and related melting points were also determined. The anticancer activity was evaluated using MTT procedure in-vitro. All compounds were tested against SKNMC (Neuroblastoma), HT-29 (Colon cancer) and PC3 (Prostate cancer) cell lines. According to the toxicological data, none of the synthesized derivatives exerted superior activity than doxorubicin as reference drug. Derivatives with Ortho chlorine (compound 3d), meta methoxy (compound 3h) and meta fluorine (compound 3b) substituents on the phenyl ring exhibited the best cytotoxic activity against SKNMC (IC(50) = 4.5 ± 0.035 µM), HT-29 (IC(50) = 3.1 ± 0.030 µM) and PC3 (IC(50) = 12.6 ± 0.302 µM) cell lines respectively.
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spelling pubmed-41570232014-09-18 N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents Mohammadi-Farani, Ahmad Heidarian, Neda Aliabadi, Alireza Iran J Pharm Res Original Article A new series of N-(5-Mercapto-1,3,4-thiadiazol-2-yl)-2-phenylacetamide derivatives (3a-3j) were synthesized via an amidation reaction using EDC and HOBt in acetonitrile solvent at room temperature condition. Chemical structures were characterized by (1)H NMR, IR and MS spectroscopic methods and related melting points were also determined. The anticancer activity was evaluated using MTT procedure in-vitro. All compounds were tested against SKNMC (Neuroblastoma), HT-29 (Colon cancer) and PC3 (Prostate cancer) cell lines. According to the toxicological data, none of the synthesized derivatives exerted superior activity than doxorubicin as reference drug. Derivatives with Ortho chlorine (compound 3d), meta methoxy (compound 3h) and meta fluorine (compound 3b) substituents on the phenyl ring exhibited the best cytotoxic activity against SKNMC (IC(50) = 4.5 ± 0.035 µM), HT-29 (IC(50) = 3.1 ± 0.030 µM) and PC3 (IC(50) = 12.6 ± 0.302 µM) cell lines respectively. Shaheed Beheshti University of Medical Sciences 2014 /pmc/articles/PMC4157023/ /pubmed/25237343 Text en © 2014 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Mohammadi-Farani, Ahmad
Heidarian, Neda
Aliabadi, Alireza
N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title_full N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title_fullStr N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title_full_unstemmed N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title_short N-(5-Mercapto-1,3,4-Thiadiazol-2-yl)-2-Phenylacetamide Derivatives: Synthesis and In-vitro Cytotoxicity Evaluation as Potential Anticancer Agents
title_sort n-(5-mercapto-1,3,4-thiadiazol-2-yl)-2-phenylacetamide derivatives: synthesis and in-vitro cytotoxicity evaluation as potential anticancer agents
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4157023/
https://www.ncbi.nlm.nih.gov/pubmed/25237343
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