Acylsulfonamide

Last updated April 02, 2025

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 R−CO−NH−SO₂−R′. 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

The following are approved drugs that contain the acylsulfonamide functional group:

Several investigational new drugs contain also the acylsulfonamide functional group. Examples include:

References

↑ 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.
1 2 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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[Ammazzalorso_2017-1] 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.

[Francisco_2021-2] 1 2 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_2023-3] 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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