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Novel 9-(Alkylthio)-Acenaphtho[1,2-E]-1,2,4-Triazine Derivatives: Synthesis, Cytotoxic Activity and Molecular Docking Studies on B-Cell Lymphoma 2 (Bcl-2) Publisher



Mohammadi MK1 ; Firuzi O2 ; Khoshneviszadeh M2 ; Razzaghiasl N3 ; Sepehri S4 ; Miri R2, 3
Authors
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Authors Affiliations
  1. 1. Faculty of Sciences, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
  2. 2. Medicinal and Natural Products Chemistry Research Center, Shiraz, University of Medical Sciences, Shiraz, PO Box 3288-71345, Iran
  3. 3. Departments of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Departments of Medicinal Chemistry, Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran

Source: DARU, Journal of Pharmaceutical Sciences Published:2014


Abstract

Background and purpose of the study. Acenaphtho derivatives have been reported as antitumor agents. Due to this fact and also with the aim of developing the chemistry of potentially bioactive heterocyclic compounds via efficient reactions, a facile procedure for the synthesis of 9-(alkylthio)-acenaphtho[1,2-e]-1,2,4-triazines via two step condensation of thiosemicarbazide and acenaphtylene-9,10-quinone to form acenaphtho[1,2-e]-1,2, 4-triazine-9(8H)-thiones and subsequent reaction with benzyl chloride derivatives is reported. Methods. 9-(alkylthio) acenaphtho[1,2-e]-1,2,4- triazines were synthesized via the reaction of acenaphtho-9,10-quinone with thiosemicarbazide, and then with the benzyl chloride derivatives. Cytotoxicity of some prepared compounds was assessed through MTT assay on three different human cancerous cell lines (HL-60, MCF7, and MOLT-4 cells). Molecular docking studies were performed via AutoDock4.2 software in order to confirm an apoptosis-inducing activity of acenaphtho scaffolds via the Bcl-2 protein. Results: Excellent yields of the products, short reaction times and simple work-up are attractive features of this synthetic protocol. The evaluated compounds exhibited moderate to good cytotoxic activities. Docking results on the active site of B-cell lymphoma 2 (Bcl-2) supported the experimental biological data and agreed well with previous in silico data for commonly used anti-cancer drugs. Moreover; results were analyzed considering binding efficiency indices. Conclusions: The outcomes of the present study may be helpful in future targeting of Bcl-2 with the aim of developing apoptosis-inducing agents. © 2014 Mohammadi et al.; licensee BioMed Central Ltd.
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