Synthesis of Isothiocyanates Using DMT/NMM/TsO− as a New Desulfurization Reagent
| Autor: | Dorota Kregiel, Beata Kolesinska, Łukasz Janczewski |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
isothiocyanates
desulfurization agent microwave-assisted synthesis of biologically active compounds Pharmaceutical Science 010402 general chemistry 01 natural sciences microwave synthesis Analytical Chemistry chemistry.chemical_compound QD241-441 antibacterial activity Drug Discovery Organic chemistry Physical and Theoretical Chemistry Racemization Alkyl chemistry.chemical_classification amino acids Organic base 010405 organic chemistry Chemistry Aryl 4-(4 6-dimethoxy-1 3 5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate Organic Chemistry Absolute configuration microwave technology circular dichroism 0104 chemical sciences Amino acid Chemistry (miscellaneous) Reagent Isothiocyanate Molecular Medicine DMT/NMM/TsO |
| Zdroj: | Molecules Volume 26 Issue 9 Molecules, Vol 26, Iss 2740, p 2740 (2021) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26092740 |
| Popis: | Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO−) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L- and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e. |
| Databáze: | OpenAIRE |
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