143769-97-5Relevant academic research and scientific papers
Structure property relationships of N-acylsulfonamides and related bioisosteres
Ballatore, Carlo,Brancale, Andrea,Francisco, Karol R.,Kozlowski, Marisa C.,Paniak, Thomas J.,Varricchio, Carmine
, (2021)
The N-acylsulfonamide functional group is a feature of the pharmacophore of several biologically active molecules, including marketed drugs. Although this acidic moiety presents multiple points of attachments that could be exploited to introduce structural diversification, depending on the circumstances, the replacement of the functional group itself with a suitable surrogate, or bioisostere, may be desirable. A number of N-acylsulfonamide bioisosteres have been developed over the years that provide opportunities to modulate both structure and physicochemical properties of this important structural motif. To enable an assessment of the relative impact on physicochemical properties that these replacements may have compared to the N-acylsulfonamide group, we conducted a structure-property relationship study based on matched molecular pairs, in which the N-acylsulfonamide moiety of common template reference structures is replaced with a series of bioisosteres. The data presented, which include an assessment of relative changes in acidity, permeability, lipophilicity and intrinsic solubility, provides a basis for informed decisions when deploying N-acylsulfonamides, or surrogates thereof, in analog design.
Intramolecular Sulphonamidomethylation. Part II. Fused Heterocycles from 2-Phenylethanesulphonamides
Zinczuk, Juan,Sorokin, Isidoro H.,Orazi, Orfeo O.,Corral, Renee A.
, p. 859 - 866 (2007/10/02)
1,2,4,5-Tetrahydro-3,2-benzothiazepine 3,3-dioxides 2, with a variety of substituents on the nitrogen atom, can be easily obtained by the title reaction.The isomeric compounds 4-6 are also formed from sulphonamides bearing an N-aralkyl group with a chain
