Synthesis of functionalized sulfonamides as antitubercular agents

Abstract

Using up-to-date methods for synthesis and analysis, 51 sulfonamides were prepared for use as tools in antitubercular drug discovery. The synthetic efforts were centered on varying substituents at three key structural units implicated in antimicrobial activity, namely the sulfonyl group, nitrogen N¹ and nitrogen N⁴. Procedures were specific to the sites of functionalization. Preliminary biological assessments are included here on selected compounds. The results suggest that the compounds may be useful in the exploration of the likely interactions of sulfa drugs with enzymes found in tuberculosis (dihydropteroate synthase) or its human host (N-acetyltransferase), interactions that result in drug activity or drug de-activation, respectively.

GRAPHICAL ABSTRACT

Keywords:

• Sulfa drugs
• tuberculosis
• N-acetyltransferase
• dihydropteroate synthase
• biological assessment

Acknowledgements

This work was taken in part from the Wellesley College Bachelor of Arts Honors Thesis of CDP, who thanks her committee members, Professors Christopher Arumainayagam, Dora Carrico-Moniz and Daniel Chiasson, for their guidance.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by Wellesley College.