7217-84-7Relevant articles and documents
1,3-Thiazines, XXIX: The applicability of cystein derivatives in the synthesis of 5-aminotetrahydro-1,3-thiazines
Hanefeld
, p. 375 - 377 (1985)
-
Comparative reactivity analysis of small-molecule thiol surrogates
ábrányi-Balogh, Péter,Imre, Tímea,Keser?, Gy?rgy Miklós,Petri, László,Varga, Petra Regina
, (2020/02/22)
Targeted covalent inhibitors represent an increasingly popular approach to modulate challenging drug targets. Since covalent and non-covalent interactions are both contributing to the affinity of these compounds, evaluation of their reactivity is a key-step to find feasible warheads. There are well-established HPLC- and NMR-based kinetic assays to tackle this task, however, they use a variety of cysteine-surrogates including cysteamine, cysteine or acetyl-cysteine and GSH. The diverse nature of the thiol sources often makes the results incomparable that prevents compiling a comprehensive knowledge base for the design of covalent inhibitors. To evaluate kinetic measurements from different sources we performed a comparative analysis of the different thiol surrogates against a designed set of electrophilic fragments equipped with a range of warheads. Our study included seven different thiol models and 13 warheads resulting in a reactivity matrix analysed thoroughly. We found that the reactivity profile might be significantly different for various thiol models. Comparing the different warheads, we concluded that – in addition to its human relevance - glutathione (GSH) provided the best estimate of reactivity with highest number of true positives identified.
Medium buffer effects on the condensation of l -cysteine and aryl nitriles to (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic acids
Maltsev, Oleg V.,Walter, Valerianne,Brandl, Matthias J.,Hintermann, Lukas
, p. 2763 - 2767 (2013/10/21)
The condensation of l-cysteine and aryl nitriles to (R)-2-aryl-4,5- dihydrothiazole-4-carboxylic acids in buffered media was reinvestigated. Pure products (yields of 58-95%; up to 99% ee) were obtained in a NaHCO 3/NaOH-buffered aqueous alcoholic medium. Georg Thieme Verlag Stuttgart New York.