First synthesis of pyrene-functionalized silatranes for mechanistic insights into their potential anti-parasitic and anti-oxidation activities. (16th November 2017)

• Record Type: Journal Article
• Authors: Singh, Gurjaspreet; Singh, Akshpreet; Singh, Jasbhinder; Aulakh, Darpandeep; Wriedt, Mario; Espinosa, Cristóbal; Esteban, M. Angeles; Sehgal, Rakesh; Goyal, Kapil; Sinha, Shweta
• Is Part Of: New journal of chemistry. Volume 41:Number 24(2017)
• Page Start: 15165
• Page End: 15172
• Publication Date: 2017-11-16
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj03338a
• Languages: English
• ISSNs: 1144-0546

Abstract

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. 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 ( 1 H and 13 C) 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.