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. (28th January 2019)

• Record Type: Journal Article
• Authors: Soltani Rad, Mohammad Navid; Behrouz, Somayeh; Mohammadtaghi‐Nezhad, Javad; Zarenezhad, Elham; Agholi, Mahmoud
• Is Part Of: Applied organometallic chemistry. Volume 33:Number 4(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2019-01-28
• Subjects: 1, 2, 3‐triazolyl‐based metronidazole hybrid analogue -- 2‐methyl‐5‐nitro‐1‐prop‐2‐ynyl‐1H‐imidazole -- Giardia lamblia -- STCATSC -- β‐Azidoalcohol; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.4799
• Languages: English
• ISSNs: 0268-2605

Abstract

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‐1 H ‐imidazole with diverse β‐azidoalcohols in a THF‐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‐1 H ‐imidazol‐1‐yl)methyl)‐1 H ‐1, 2, 3‐triazol‐1‐yl)‐3‐phenethoxypropan‐2‐ol and 1‐(4‐((2‐methyl‐5‐nitro‐1 H ‐imidazol‐1‐yl)methyl)‐1 H ‐1, 2, 3‐triazol‐1‐yl)‐3‐(3‐phenylpropoxy)propan‐2‐ol are demonstrated to exhibit the potent antigiardial activity even stronger than metronidazole. Abstract : Silica‐tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano‐catalyst has been fabricated and used to synthesis of the new 1, 2, 3‐triazolyl‐based metronidazole hybrid analogues which exhibiting potent antigiardial activity.