Acylsulfonamide is a functional group in organic chemistry that is sometimes used in medicinal chemistry.[1] It consists of a sulfonamide group (SO2NH) linked to an acyl group (RCO), forming the structure R1-CO-NH-SO2-R2. This moiety is found in several biologically active molecules and marketed drugs, serving as an useful pharmacophore.[2] Acylsulfonamides are of particular interest due to their ability to act as bioisosteres of carboxylic acids, offering similar hydrogen bonding capabilities and comparable pKa values (typically between 3.5-4.5).[2] They are incorporated in various drugs candidates targeting conditions such as bacterial infections, pain, and cancer.[3]
Examples
editThe following are approved drugs that contain the acylsulfonamide functional group:
Several investigational new drugs contain also the acylsulfonamide functional group. Examples include:
References
edit- ^ Ammazzalorso A, De Filippis B, Giampietro L, Amoroso R (December 2017). "N-acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry". Chemical Biology & Drug Design. 90 (6): 1094–1105. doi:10.1111/cbdd.13043. PMID 28632928.
- ^ a b Francisco KR, Varricchio C, Paniak TJ, Kozlowski MC, Brancale A, Ballatore C (June 2021). "Structure property relationships of N-acylsulfonamides and related bioisosteres". European Journal of Medicinal Chemistry. 218: 113399. doi:10.1016/j.ejmech.2021.113399. PMC 8105289. PMID 33823393.
- ^ Amador R, Tahrioui A, Barreau M, Lesouhaitier O, Smietana M, Clavé G (August 2023). "N-Acylsulfonamide: a valuable moiety to design new sulfa drug analogues". RSC Medicinal Chemistry. 14 (8): 1567–1571. doi:10.1039/d3md00229b. PMC 10429802. PMID 37593573.
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