Chemistry:Acylsulfonamide
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–SO
2–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:
- Elexacaftor
- Grazoprevir
- Parecoxib
- Selexipag
- Simeprevir
- Sulfacetamide
- Sulfadicramide
- Sulfisoxazole acetyl
- Vaniprevir
- Venetoclax
- Voxilaprevir
- Zafirlukast
Several investigational new drugs contain also the acylsulfonamide functional group. Examples include:
References
- ↑ "N-acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry". Chemical Biology & Drug Design 90 (6): 1094–1105. December 2017. doi:10.1111/cbdd.13043. PMID 28632928.
- ↑ 2.0 2.1 "Structure property relationships of N-acylsulfonamides and related bioisosteres". European Journal of Medicinal Chemistry 218. June 2021. doi:10.1016/j.ejmech.2021.113399. PMID 33823393.
- ↑ "N-Acylsulfonamide: a valuable moiety to design new sulfa drug analogues". RSC Medicinal Chemistry 14 (8): 1567–1571. August 2023. doi:10.1039/d3md00229b. PMID 37593573.
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