Synthesis and hypoglycemic activity of some substituted 2-arylthiazolo[3.2-a]pyridinium salts

Abstract

A series of substituted 2-arylthiazolo[3,2-a]pyridinium salts (1a-q) was prepared by known methods and tested for hypoglycemic activity in 48-h fasted rats. Two compounds, 2-phenylthiazolo- and 8-methyl-2-phenythiazolo[3,2-a]pyridinium perchlorate (1a and 1q), showed consistent hypoglycemic activity in this screen, demonstrating that a high degree of structural specificity was required for hypoglycemic activity. At higher doses the hypoglycemic activity of 1a and 1q was associated with elevated levels of hepatic triglycerides.

Design and synthesis of novel pyridinium nitrate-bearing substituted anilines via one-pot tandem reactions

“…Thirty-two novel pyridinium nitrate derivatives were synthesised via a one-pot tandem reaction. Their structures were elucidated by 1 H NMR, 13 C NMR and HRMS; the configuration of compound 5b was determined by X-ray crystallographic analysis. A potential reaction mechanism has been proposed.…”

“…A new and simple synthesis route has been developed for synthesising novel pyridinium nitrates with anilines that contain substituents with different electronegativities (-H, -CH 3 , -OCH 3 , -F and -Cl) and positions (C2, C3 and C4) (Scheme 1). The structures of these compounds were characterised by 1 H NMR, 13 C NMR and HRMS; the configuration of compound 5b was determined by X-ray crystallographic analysis. A possible reaction mechanism is proposed, and the substituent-reactivity relationship of a series of anilines is established.…”

Heterocycles with a Bridging Nitrogen Atom. 17. Unexpected Formation of Indolizine during the Preparation of (2-Thioxopyridin-1-yl) Acetate

“…The strategy of obtaining N-alkylpyridine-2-thiones by the reaction N-alkyl-2-halopyridinium salts with aqueous solutions of sodium sulfide is well known (for example, N-phenacylpyridine-2-thiones were made in this way [7,8]). In its turn, the bromopyridinium salt starting material 2 has been described [9], but the possibility of its conversion into the thione 1 has not been studied.…”

Carbon-Sulfur and Carbon-Selenium Double Bond Formation Through Thiolysis and Selenolysis of 4-Methylsulfanyl-Substituted Pyridinium and Quinolinium Halides

“…Specific important uses of the 2-pyridinethiones are as synthetic intermediates 12 and in heterocyclic synthesis. 13 In connection with our studies on the alkylidenation of suitably 4-sulfanyl-functionalized pyridinium and quinolinium cations via the sulfur contraction process, 14 and in view of the possibilities of employing thiocarbonyl and selenocarbonyl pyridine systems as potential radical scavengers and as chemical intermediates, we have undertaken a study of their preparation.…”

“…1 H NMR and13 C NMR Spectral Data of Selected N-Substituted Pyridine-4-thiones and Quinoline-4-thiones (CDCl 3 /TMS)…”