Carboxylic Acid Bioisosteres in Medicinal Chemistry: Synthesis and ...
Acyl sulfonamides are well-known carboxylic acid bioisosteres in drugs as they have improved pharmacological properties compared to carboxylic acids, such as its metabolic resistance against glucuronidation, which is due to an enhanced chemical and enzymatic stability of the sulfonamide moiety as compared to carboxylic acids [3, 114].
N-acylsulfonamides: Synthetic routes and biological potential …
Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors.
Bioisoteres for carboxylic acids: From ionized isosteres to novel ...
2024年4月15日 · This review initially details carefully selected examples whereby tetrazoles, acyl sulfonamides or isoxazolols have been beneficially utilized as carboxylic acid bioisosteres altering physicohemical properties, interactions with the target and metabolism and/or pharmacokinetics, before delving further into the binding mode of carboxylic acid der...
We report here on the anion binding properties of these highly acidic N H functional groups. We have prepared two new calixarene-based tetrazole-containing hosts, as well as new acetyl sulfonamide and benzoyl sulfonamide hosts. We also report on analogous hosts bearing the better-known aryl sulfonamide functional group as a point of comparison.
Drug Design: Influence of Heterocyclic Structure as Bioisosteres
Examples of classical carboxylic acid bioisosteres are the trifluoromethyl ketones and the sulfonamide derivatives, even though they do not share the planarity of the carboxylic acid. On the other hand, the aromatic heterocycles from which the tetrazole moiety is the best known and most investigated, do exhibit a planar geometry.
Structure property relationships of N-acylsulfonamides and related ...
2021年6月5日 · Design and syntheses of matched molecular pairs of N- acylsulfonamides and related bioisosteres are described. Structure property relationship studies show that these structures cover a wide range of physicochemical properties. Comparison of Gaussian-optimized geometry and electrostatic potential maps show similar electrostatic potentials.
Routes to Drug Design Via Bioisosterism of Carboxyl and Sulfonamide …
2017年11月9日 · In this study the bioisosterism of the sulfonamide and the carboxyl groups will be investigated using molecular ESPs and average electron densities. A carboxyl group could be substituted by a sulfonamide bioisostere [37] in angiotensin II receptor antagonists [38].
Facile preparation of N-acylsulfonamides by using sulfonyl …
2007年1月29日 · N-Acylsulfonamide is widely used as a carboxylic acid bioisostere. A rapid and mild acyl sulfonamide preparation methodology from carboxylic acid and arylsulfonyl isocyanate in the presence of amine is described. The preparation of biologically active acylsulfonamide by our methodology is also presented.
N-Acyl-N-alkyl/aryl Sulfonamide Chemistry Assisted by Proximity …
2024年12月11日 · Our group revealed that N-acyl-N-alkyl sulfonamide (NASA) moieties can rapidly and efficiently acylate noncatalytic (i.e., less reactive) lysine residues in proteins by leveraging a reaction acceleration effect via proximity. The excellent reaction kinetics and selectivity for lysine of the NASA chemistry enable covalent modification of natural ...
N‐acylsulfonamides: Synthetic routes and biological potential in ...
2017年6月20日 · Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to...