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

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...

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Published in:New journal of chemistry 2017, Vol.41 (24), p.15165-15172
Main Authors: Singh, Gurjaspreet, Singh, Akshpreet, Singh, Jasbhinder, Aulakh, Darpandeep, Wriedt, Mario, Espinosa, Cristóbal, Esteban, M. Angeles, Sehgal, Rakesh, Goyal, Kapil, Sinha, Shweta
Format: Article
Language:English
Subjects:
Antioxidants
Chemical synthesis
Giardia
Infrared spectroscopy
Ionization
Ions
Mass spectrometry
NMR
Nuclear magnetic resonance
Oxidation
Single crystals
Thermogravimetric analysis
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/C7NJ03338A