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)

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MOHAMMADI MOHAMMAD K.; FIRUZI OMIDREZA; KHOSHNEVISZADEH MEHDI; RAZZAGHI ASL NIMA; SEPEHRI SAGHI; MIRI RAMIN

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Journal Paper

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Journal: DARU Journal of Pharmaceutical Sciences Year:2014 | Volume:22 | Issue:1 Page(s): 1-11

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Title

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)

Author(s)

Keywords

SYNTHESIS

ACENAPHTHO-9

10-QUINONE

CYTOTOXIC ACTIVITY

DOCKING

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.

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APA: Copy

MOHAMMADI, MOHAMMAD K., FIRUZI, OMIDREZA, KHOSHNEVISZADEH, MEHDI, RAZZAGHI ASL, NIMA, SEPEHRI, SAGHI, & MIRI, RAMIN. (2014). 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). DARU JOURNAL OF PHARMACEUTICAL SCIENCE, 22(1), 1-11. SID. https://sid.ir/paper/275734/en

Vancouver: Copy

MOHAMMADI MOHAMMAD K., FIRUZI OMIDREZA, KHOSHNEVISZADEH MEHDI, RAZZAGHI ASL NIMA, SEPEHRI SAGHI, MIRI RAMIN. 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). DARU JOURNAL OF PHARMACEUTICAL SCIENCE[Internet]. 2014;22(1):1-11. Available from: https://sid.ir/paper/275734/en

IEEE: Copy

MOHAMMAD K. MOHAMMADI, OMIDREZA FIRUZI, MEHDI KHOSHNEVISZADEH, NIMA RAZZAGHI ASL, SAGHI SEPEHRI, and RAMIN MIRI, “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),” DARU JOURNAL OF PHARMACEUTICAL SCIENCE, vol. 22, no. 1, pp. 1–11, 2014, [Online]. Available: https://sid.ir/paper/275734/en

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