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First synthesis of pyrene-functionalized silatranes for mechanistic insights into their potential anti-parasitic and anti-oxidation activities

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Abstract

The known silatranes have attached substituents such as hydrogen, organyl, organoxy, aminoalkyl, thioorganyl, acyloxy, halogen, pseudohalogen, and other groups; however, their functionalization with any polycyclic aromatic hydrocarbon substituent is not recognized; this creates a niche in silatrane chemistry. The current study involves the first synthesis of pyrene-functionalized silatranes starting from 1-pyrenecarboxaldehyde and aminopropylsilane, fulfilling the niche. These newly synthesized silatranes were structurally characterized by IR spectroscopy, multinuclear NMR (1H and 13C) spectroscopy, electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS), and thermogravimetric analysis, and the structure of one of the silatranes was further confirmed by single crystal XRD analysis. The protozoans Giardia lamblia and Trichomonas vaginalis are responsible for a significant number of intestinal infections, and antioxidants are needed to prevent the formation of reactive species in the body. In the present study, anti-oxidant, anti-giardiasis, and anti-trichomoniasis potential of the synthesized compounds were assessed. Both compounds displayed significant activity against G. lamblia and T. vaginalis and showed potential anti-oxidant activity. The results indicate that one of the compounds is even more active against G. lamblia than metronidazole, a standard drug. Moreover, a theoretically and electrochemically supported mechanism for the anti-oxidant activity of the compounds has been reported in this study.

Graphical abstract: First synthesis of pyrene-functionalized silatranes for mechanistic insights into their potential anti-parasitic and anti-oxidation activities

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Publication details

The article was received on 04 Sep 2017, accepted on 01 Nov 2017 and first published on 02 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03338A
Citation: New J. Chem., 2017, Advance Article
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    First synthesis of pyrene-functionalized silatranes for mechanistic insights into their potential anti-parasitic and anti-oxidation activities

    G. Singh, A. Singh, J. Singh, D. Aulakh, M. Wriedt, C. Espinosa, M. A. Esteban, R. Sehgal, K. Goyal and S. Sinha, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ03338A

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