4 research outputs found
Design and synthesis of imidazole and triazole pyrazoles as mycobacterium tuberculosis CYP121A1 inhibitors
- Author
- Publication venue
- 'Wiley'
- Publication date
- 01/01/2019
- Field of study
The emergence of untreatable drugâresistant strains of Mycobacterium tuberculosis is a major public health problem worldwide, and the identification of new efficient treatments is urgently needed. Mycobacterium tuberculosis cytochrome P450 CYP121A1 is a promising drug target for the treatment of tuberculosis owing to its essential role in mycobacterial growth. Using a rational approach, which includes molecular modelling studies, three series of azole pyrazole derivatives were designed through two synthetic pathways. The synthesized compounds were biologically evaluated for their inhibitory activity towards M. tuberculosis and their protein binding affinity (KD). Series 3 biarylpyrazole imidazole derivatives were the most effective with the isobutyl (10âf) and tertâbutyl (10âg) compounds displaying optimal activity (MIC 1.562â
ÎŒg/mL, KD 0.22â
ÎŒM (10âf) and 4.81â
ÎŒM (10âg)). The spectroscopic data showed that all the synthesised compounds produced a type II red shift of the heme Soret band indicating either direct binding to heme iron or (where less extensive Soret shifts are observed) putative indirect binding via an interstitial water molecule. Evaluation of biological and physicochemical properties identified the following as requirements for activity: LogP >4, Hâbond acceptors/Hâbond donors 4/0, number of rotatable bonds 5â6, molecular volume >340â
Ă
3, topological polar surface area <40â
Ă
2
Canada
- Author
- A. Burke
- A. J. M. Smith
- Alford Edna
- Alianak Hrant
- Allan Safarik
- Anne Szumigalski
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- Atwood Margaret
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