Studies on dihydropyridines. III. Synthesis of 4,7-dihydrothieno(2,3-b)pyridines with vasodilator and antihypertensive activities.

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

“…From the symmetric ketone 47 the Gewald thiophene synthesis was conducted in a stepwise fashion through Knoevenagel-Cope condensation to give the intermediate 48 followed by base-promoted thiophene cyclization with sulfur. [35][36][37] From the 2-aminothiophene-3-carbonitrile 49a or methyl 2-aminothiophene-3-carboxylate 49b the annulation of pyridine was performed using common pyrimidine annelation with guanidine carbonate 50a or chloroformamidine hydrochloride 50b (Method A, Scheme 19). 129 In a second approach the aldehyde derivative 49c was prepared first in three steps and then annelated under the same conditions as before (Method B, Scheme 19).…”

“…Because the structure-based drug design program through substituted 2-aminothiophenes has been investigated broadly, up to this date there are many other research works dealing with the synthesis, pharmacology and application of thiophene-based structures in medicinal chemistry. 7,[12][13][14]36,37,51,69,100,101,[119][120][121][122][123][124][125][126][127] It is no doubt, that this area of Gewald-like thiophene derivatives exhibits the highest progress in a scope and utilization.…”

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

“…The thieno [2,3-b]pyridine derivatives occupy special place and have attracted considerable attention because of their broad pharmacological activities, including anticancer [1][2][3][4][5][6][7][8][9], antiviral [10][11][12][13], anti-inflammatory [14][15][16][17], antimicrobial [18,19], antidiabetic [20][21][22][23], antihypertensive [24][25][26] and osteogenic [27,28] activities, in addition to treatment of CNS disorders [29][30][31].…”

Novel Nicotinonitriles and Thieno[2,3‐b]pyridines as Potent Biofilm and COX‐2 Inhibitors: Synthesis, In Vitro and In Silico Studies

“…[29] Moreover, thieno [2,3-b]pyridine derivatives showed tremendous medicinal and biological activities as antimicrobial, [30,31] antiviral, [32,33] anti-inflammatory, [34][35][36] antidiabetic [37,38] and antihypertensive agents. [39] They also act as potent inhibitors for DNA gyrase, [40] and COX-2 enzymes. [41] Figure 1 represented the structure of some pyridine-2(1H)thiones I-III, nicotinonitriles IV-VI and thieno [2,3-b]pyridines VII and VIII of potent antibacterial activities.…”