Methyl 2-Amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate

Abstract

Methyl 2-amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate as a newly functionalized heterocyclic amino acid was obtained via [3+2] cycloaddition. The structure of the novel 1,3-selenazole was unequivocally confirmed by detailed 1H, 13C, 15N, and 77Se NMR spectroscopic experiments, HRMS and elemental analysis.

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

“…The synthetic strategy for the synthesis of novel functionalized 1,2-oxazole derivatives is outlined in Scheme 1. The synthetic sequence began with preparing β-keto esters 2a-h by treating N-Boc-protected cyclic amino acids 1a-h with Meldrum's acid in the presence of EDC•HCl and DMAP, followed by methanolysis of the corresponding adducts [27,28,31,[36][37][38]. Reaction of the resulting β-keto esters 2a-h with N,N-dimethylformamide dimethylacetal afforded cycloaminyl β-enamino ketoesters 3a-h. After isolation of compounds 3a-h from the corresponding reaction mixtures, they were identified using LC-MS analysis, and were immediately treated with hydroxylamine hydrochloride in an appropriate solvent to obtain the target 1,2oxazoles 4a-h. A representative β-enamino ketoester 3a was subjected to a detailed NMR analysis (Figure 2a).…”

“…The synthetic strategy for the synthesis of novel functionalized 1,2-oxazole derivatives is outlined in Scheme 1 . The synthetic sequence began with preparing β-keto esters 2a – h by treating N -Boc-protected cyclic amino acids 1a – h with Meldrum’s acid in the presence of EDC·HCl and DMAP, followed by methanolysis of the corresponding adducts [ 27 – 28 31 , 36 – 38 ]. Reaction of the resulting β-keto esters 2a – h with N , N -dimethylformamide dimethylacetal afforded cycloaminyl β-enamino ketoesters 3a – h .…”

“…Recently, a highly specific and potent p38α kinase inhibitor containing a 3-amino-1-phenyl-1H-pyrazole-4-carboxylic acid residue was identified directly from the 12.6-million-member DNA-encoded small molecule library using yoctoReactor technology [26]. We have developed efficient protocols that provide easy access to highly functional heterocyclic compounds as novel amino acid-like building blocks by combining thiazole, selenazole, pyrazole, indazole, and indole moieties with both carboxyl functional groups and cycloaminyl units [27][28][29][30][31].…”

Synthesis and neuroprotective activity of 3‐aryl‐3‐azetidinyl acetic acid methyl ester derivatives

“…[40] In our recent work, we have been pursuing the construction of amino acid-like functionalized heterocyclic molecules possessing azetidine core. [41][42][43][44] In this study, we prepared a library of 3-aryl-3-azetidinyl acetic acid methyl ester derivatives, assessed their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity, and determined their neuroprotective effect in salsolinol (SAL)-induced model of PD and glutamate (Glu)-induced model of oxidative damage on neuron-like SH-SY5Y cells. Consequently, cholinesterase inhibition, alongside neuroprotective effect in Gluinduced Xc-antiporter inhibition models could offer a new strategy for disease-modifying AD and PD therapy.…”