Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space
| Autor: | Yuriy G. Shermolovich, Vadim M. Timoshenko, Oleksii Gavrylenko, Serhii Zhersh, Sergiy V. Zasukha, Andrey A. Tolmachev, Oleksandr O. Grygorenko, Valentyna O. Pivnytska |
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| Rok vydání: | 2019 |
| Předmět: |
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Molecular Chemistry Techniques Synthetic Imides 010402 general chemistry 01 natural sciences Catalysis Mice X-Ray Diffraction Microsomes Nucleophilic substitution Animals Reactivity (chemistry) Diamide Substitution reaction Sulfonamides Sulfur Compounds 010405 organic chemistry Chemistry Organic Chemistry General Chemistry Combinatorial chemistry Chemical space 0104 chemical sciences Molecular geometry Reagent Electrophile Indicators and Reagents Organosulfur compounds |
| Zdroj: | Chemistry – A European Journal. 25:6928-6940 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201900440 |
| Popis: | 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, pKa , 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. |
| Databáze: | OpenAIRE |
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