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Molecules 2015, 20(4), 5360-5373; doi:10.3390/molecules20045360

Synthesis, Antiproliferative Activity and Molecular Properties Predictions of Galloyl Derivatives

1
Faculdade de Ciências Biológicas e Ambientais, Universidade Federal da Grande Dourados, Rodovia Dourados—Itahum, Km 12, Dourados, 79.804-970 MS, Brazil
2
Faculdade de Ciências Exatas e Tecnologia, Universidade Federal da Grande Dourados, Rodovia Dourados—Itahum, Km 12, Dourados, 79.804-970 MS, Brazil
3
Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas, Universidade Estadual de Campinas, 6171, Campinas, 13083-970 SP, Brazil
4
Faculdade de Ciências Agrárias, Universidade Federal da Grande Dourados, Rodovia Dourados—Itahum, Km 12, Dourados, 79.804-970 MS, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 11 November 2014 / Revised: 6 March 2015 / Accepted: 9 March 2015 / Published: 25 March 2015
View Full-Text   |   Download PDF [701 KB, uploaded 25 March 2015]   |  

Abstract

The present study was designed to investigate the in vitro antiproliferative activity against ten human cancer cell lines of a series of galloyl derivatives bearing substituted-1,3,4-oxadiazole and carbohydrazide moieties. The compounds were also assessed in an in silico study of the absorption, distribution, metabolism and excretion (ADME) in the human body using Lipinski’s parameters, the topological polar surface area (TPSA) and percentage of absorption (%ABS). In general, the introduction of N'-(substituted)-arylidene galloyl hydrazides 48 showed a moderate antitumor activity, while the 2-methylthio- and 2-thioxo-1,3,4-oxadiazol-5-yl derivatives 9 and 10 led to increased inhibition of cancer cell proliferation. The precursor compound methyl gallate 2 and the intermediary galloyl hydrazide 3 showed greater antiproliferative activity with GI50 values < 5.54 µM against all human tumor cell lines tested. A higher inhibition effect against ovarian cancer (OVCAR-3) (GI50 = 0.05–5.98 µM) was also shown, with compounds 2, 3, 9 and 10 with GI50 ≤ 0.89 µM standing out in this respect. The in silico study revealed that the compounds showed good intestinal absorption. View Full-Text
Keywords: galloyl; hydrazide; oxadiazole; antiproliferative activity; in silico study galloyl; hydrazide; oxadiazole; antiproliferative activity; in silico study
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Maximo da Silva, M.; Comin, M.; Santos Duarte, T.; Foglio, M.A.; de Carvalho, J.E.; do Carmo Vieira, M.; Nazari Formagio, A.S. Synthesis, Antiproliferative Activity and Molecular Properties Predictions of Galloyl Derivatives. Molecules 2015, 20, 5360-5373.

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