Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Abstract

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

“…The combination of coumarin and a thiazole ring is of great significance in pharmaceutical chemistry. Coumarin–thiazole compounds have shown many biological activities such as anti-acetylcholinesterase [ 25 ], anti-inflammatory [ 26 ], antibacterial and antituberculosis agents [ 27 ], antioxidant, and inhibition of carbonic anhydrase [ 28 , 29 ] (Fig. 1 ).…”

Thieno-Thiazolostilbenes, Thienobenzo-Thiazoles, and Naphtho-Oxazoles: Computational Study and Cholinesterase Inhibitory Activity

“…The organic layers were dried under anhydrous MgSO4. Product 8a (E)-N-(sec-butyl)-5-(2-(thiophen-2-yl)vinyl)thiazol-2-amine (trans-9a): 10 mg (isolated yield 10%), yellow oil, R f (DCM/E = 40%) = 0.24; UV (ACN) λ max /nm (ε/dm 3 mol −1 cm −1 ) 362 (10,237); 1 H NMR (CDCl 3 , 600 MHz) δ/ppm: 7.12 (d, J = 4.9 Hz, 1H), 7.05 (s, 1H), 6.97-6.93 (m, 2H), 6.90 (d, J = 15.8 Hz, 1H), 6.59 (d, J = 15.8 Hz, 1H), 5.55 (s, 1H), 3.54-3.46 (m, 1H), 1.67-1.56 (m, 2H), 1.27 (d, J = 6.4 Hz, 1H), 0.98 (t, J = 7.6 Hz, 1H); 13 Thiazolo-stilbene 8a was synthesized by McMurry reaction. The reaction apparatus was under argon, Ar atmosphere while adding the reactants.…”

“…The thiazole ring represents a very important motif with great potential in the field of medicine [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. According to the literature, some stilbene analogs containing thiazole moiety were designed, showing promising topoisomerase I inhibitory activity [16].…”