{{Short description|Functional group in organic chemistry}} {{cs1 config|name-list-style=vanc|display-authors=6}} thumb|Chemical structure of a generic acylsulfonamide '''Acylsulfonamide''' is a functional group in organic chemistry that is sometimes used in medicinal chemistry.<ref name="Ammazzalorso_2017">{{cite journal | vauthors = Ammazzalorso A, De Filippis B, Giampietro L, Amoroso R | title = N-acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry | journal = Chemical Biology & Drug Design | volume = 90 | issue = 6 | pages = 1094–1105 | date = December 2017 | pmid = 28632928 | doi = 10.1111/cbdd.13043 }}</ref> It consists of a sulfonamide group (SO<sub>2</sub>NH) linked to an acyl group (RCO), forming the structure {{chem2|R\sCO\sNH\sSO2\sR′}}. This moiety is found in several biologically active molecules and marketed drugs, serving as a useful pharmacophore.<ref name="Francisco_2021">{{cite journal | vauthors = Francisco KR, Varricchio C, Paniak TJ, Kozlowski MC, Brancale A, Ballatore C | title = Structure property relationships of N-acylsulfonamides and related bioisosteres | journal = European Journal of Medicinal Chemistry | volume = 218 | issue = | article-number = 113399 | date = June 2021 | pmid = 33823393 | pmc = 8105289 | doi = 10.1016/j.ejmech.2021.113399 }}</ref> 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 and 4.5).<ref name="Francisco_2021" /> They are incorporated in various drugs candidates targeting conditions such as bacterial infections, pain, and cancer.<ref name="Amador_2023">{{cite journal | vauthors = Amador R, Tahrioui A, Barreau M, Lesouhaitier O, Smietana M, Clavé G | title = N-Acylsulfonamide: a valuable moiety to design new sulfa drug analogues | journal = RSC Medicinal Chemistry | volume = 14 | issue = 8 | pages = 1567–1571 | date = August 2023 | pmid = 37593573 | pmc = 10429802 | doi = 10.1039/d3md00229b }}</ref>
== Examples ==
The following are approved drugs that contain the acylsulfonamide functional group: {{div col|colwidth=20em}} * Elexacaftor * Grazoprevir * Parecoxib * Selexipag * Simeprevir * Sulfacetamide * Sulfadicramide * Sulfisoxazole acetyl * Vaniprevir * Venetoclax * Voxilaprevir * Zafirlukast {{Div col end}}
Several investigational new drugs contain also the acylsulfonamide functional group. Examples include: {{div col|colwidth=20em}} * Asunaprevir * Danoprevir * Glecaprevir * Navitoclax * Paritaprevir * Sulprostone {{Div col end}}
== References == {{Reflist}}
Category:Acylsulfonamides Category:Sulfonamides Category:Functional groups
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