Silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano-catalyst for highly efficient synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues having potent antigiardial activity

Rad, Mohammad Navid Soltani and Behrouz, Somayeh and Mohammadtaghi-Nezhad, Javad and Zarenezhad, Elham and Agholi, Mahmoud (2019) Silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano-catalyst for highly efficient synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues having potent antigiardial activity. APPLIED ORGANOMETALLIC CHEMISTRY, 33 (4).

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Abstract

The preparation, characterization and application of silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano catalyst for synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues is described. STCATSC is fully characterized by different microscopic, spectroscopic and physical techniques, including scanning electron microscopy (SEM), transmission, X-ray diffraction (XRD), Energy-dispersive X-ray spectroscopy (EDS), thermogravimetric analysis (TGA), FT-IR and inductively coupled plasma (ICP) analysis. This catalyst is used to prepare the new 1,2,3-triazolyl-based metronidazole hybrid analogues. The `Click' Huisgen cycloaddition reaction of 2-methyl-5-nitro-1-prop-2-ynyl-1H-imidazole with diverse beta-azidoalcohols in a THE-water media at R.T. provides the products in good to excellent yields using STCATSC. STCATSC is proved to be a stable, low cost, reusable and environmentally benign hybrid catalyst. Products are in vitro tested against Giardia lamblia (G. lamblia) in which determined that all compounds exhibit varied promising antigiardial activity compare to metronidazole as a reference drug. Among the products, 1-(4-((2-methyl-5-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)- 3-phenethoxypropan-2-ol and 1-4-((2-methyl-5-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-3 -(3-phenylpropoxy)propan-2-ol are demonstrated to exhibit the potent antigiardial activity even stronger than metronidazole.

Item Type: Article
Uncontrolled Keywords: 1,2,3-triazolyl-based metronidazole hybrid analogue; 2-methyl-5-nitro-1-prop-2-ynyl-1H-imidazole; Giardia lamblia; STCATSC; beta-Azidoalcohol
Subjects: QV Pharmacology
Depositing User: Unnamed user with email eprints@fums.ac.ir
Date Deposited: 20 Jan 2020 07:28
Last Modified: 20 Jan 2020 07:28
URI: http://eprints.fums.ac.ir/id/eprint/2612

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