Premium
Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space
Author(s) -
Zasukha Sergiy V.,
Timoshenko Vadim M.,
Tolmachev Andrey A.,
Pivnytska Valentyna O.,
Gavrylenko Oleksii,
Zhersh Serhii,
Shermolovich Yuriy,
Grygorenko Oleksandr O.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900440
Subject(s) - organosulfur compounds , electrophile , chemical space , chemistry , reagent , nucleophile , reactivity (psychology) , combinatorial chemistry , organic chemistry , sulfur , drug discovery , catalysis , medicine , biochemistry , alternative medicine , pathology
Two novel solid reagents—1‐sulfonimidoyl‐ and 1‐sulfamimidoyl‐3‐methylimidazolium derivatives—for the synthesis of sulfonimidamides and imidosulfuric diamides, respectively, were developed. It is shown that these reagents are very effective in substitution reactions with various N‐ and O‐nucleophiles; therefore, they significantly extend the accessibility to the chemical space covered by organosulfur(VI) compounds with S=N bonds. In addition, previously unknown imidosulfuric diamides with free imino nitrogen groups were prepared, and their physical and chemical properties were characterized (including molecular geometry, p K a , Log P , microsomal stability, and reactivity towards typical electrophiles). Similar to other organosulfur(VI) derivatives with S=N bonds, these compounds can be considered as promising bioisosteres of amides, ureas, or sulfonamides.