Presentation Title

Synthesis and characterization of 1,2,3-benzotriazole derivatives and their activity against Candida species

Faculty Mentor

Robert Iafe

Start Date

23-11-2019 9:45 AM

End Date

23-11-2019 10:00 AM

Location

Markstein 203

Session

oral 1

Type of Presentation

Oral Talk

Subject Area

behavioral_social_sciences

Abstract

Candida species causes a majority of fungal infections contracted by humans and is combated with the treatment of fluconazole. This antifungal drug belongs to a class of triazoles that display bioactivity. Unfortunately, there have been several cases of drug resistance to fluconazole, creating an urgent need for new compounds that have intriguing activities, broad biological spectra, and fewer adverse effects. Benzotriazoles (BT) are a bioisostere of triazoles, which have similar physical, chemical, and biological properties. Due to BT having a wide variety of intermolecular interactions, it is used to overcome triazole resistance by being incorporated in medicines to fight cancer and infectious diseases. It has been previously shown that a 1,2,3-BT derivative displayed antifungal properties similar to fluconazole. Here we report the synthesis of 12 novel 1,1-diarylmethane BT derivatives from commercially cheap aldehydes using gold catalysis. First, diarylmethanols were synthesized from substituted aldehydes via Grignard reaction with phenylmagnesium bromide. Then, using microwave-assisted gold-catalysis methodology developed in our lab, the benzylic alcohol was displaced with BT. Using this protocol, we achieved excellent yields ranging from 60-98% and showed excellent regioselectivity at the N-1 position of 1,2,3 BT which is superior to all other methods involving acid catalysis. An in-vitro disk-diffusion assay will be conducted to test for bioactivity and to determine the minimum inhibitory concentration.

This document is currently not available here.

Share

COinS
 
Nov 23rd, 9:45 AM Nov 23rd, 10:00 AM

Synthesis and characterization of 1,2,3-benzotriazole derivatives and their activity against Candida species

Markstein 203

Candida species causes a majority of fungal infections contracted by humans and is combated with the treatment of fluconazole. This antifungal drug belongs to a class of triazoles that display bioactivity. Unfortunately, there have been several cases of drug resistance to fluconazole, creating an urgent need for new compounds that have intriguing activities, broad biological spectra, and fewer adverse effects. Benzotriazoles (BT) are a bioisostere of triazoles, which have similar physical, chemical, and biological properties. Due to BT having a wide variety of intermolecular interactions, it is used to overcome triazole resistance by being incorporated in medicines to fight cancer and infectious diseases. It has been previously shown that a 1,2,3-BT derivative displayed antifungal properties similar to fluconazole. Here we report the synthesis of 12 novel 1,1-diarylmethane BT derivatives from commercially cheap aldehydes using gold catalysis. First, diarylmethanols were synthesized from substituted aldehydes via Grignard reaction with phenylmagnesium bromide. Then, using microwave-assisted gold-catalysis methodology developed in our lab, the benzylic alcohol was displaced with BT. Using this protocol, we achieved excellent yields ranging from 60-98% and showed excellent regioselectivity at the N-1 position of 1,2,3 BT which is superior to all other methods involving acid catalysis. An in-vitro disk-diffusion assay will be conducted to test for bioactivity and to determine the minimum inhibitory concentration.