Synthesis of some new Thieno[2,3-b]pyridines, Pyrimidino[4',5':4,5]thieno[2,3-b]pyridine and Pyridines Incorporating 5-Bromobenzofuran-2-yl Moiety

Abstract

2-Sulfanyl-6-(2-thienyl)pyridine-3-carbonitrile, 1-Amino-6-(5-bromo-benzofuran-2-yl)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile, thieno [2,3-b]pyridins, pyrimidino[4',5':4,5] thieno [2,3-b]pyridine, quinazoline and carbamate derivatives were synthesized from sodium 3-(5-bromobenzofuran-2-yl)-3-oxoprop-1-en-1-olate with. The newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthesis whenever possible and chemical transportation.

The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design

“…In general, pyridine-and dihydropyridine-containing drugs are mostly used as antimicrobial, antiviral, anticancer, antioxidant, antihypertensive, antidiabetic, antimalarial, and antiinflammatory agents, psychopharmacological antagonists, and antiamebic agents. [56][57][58][59][60][61][62] A comprehensive list of commercially available drugs containing pyridine and/or dihydropyridine scaffolds and their mechanism of action is summarized in Table 1.…”

Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines

“…The system NaOH/EtOH are also used at 10 С, 44 as well as the system KOH/DMF/H 2 O at room temperature. [45][46][47][48][49][50][51][52][53] It is often impossible to carry out the synthesis one-pot, since further cyclization of nicotinonitriles 2 requires more drastic conditions. In particular, stronger bases and a higher reaction temperature necessary for the generation of key cyclization intermediates, carbanions 5.…”

“…These conditions are met by cyclization in anhydrous ethanol in the presence of EtONa upon heating, 25,31,[34][35][36][37][38]42,44,45 in DMF with CaO at 80 С, 26 using the system K 2 CO 3 /Bu 4 NBr/dioxane at 60-70 С, 27 MeONa in MeOH at refl ux, [28][29][30]32 KOH in refl uxing EtOH, 33,39-41 in DMF with aqueous KOH, 43,46,48,50,52 , and in the presence of piperidine in refl uxing EtOH. 47 A one-pot version of approach A (see Scheme 1) allows obtaining thienopyridines 3 directly from thiones 1 without isolation of nicotinonitrile 2. This pathway supposes the treatment of thions 1 with alkylating agents and an excess of a base under more harsh conditions.…”

Design, Synthesis and In‐Silico Studies of Piperidine‐Dihydropyridine Hybrids as Anticancer Agents

“…[11] Dihydropyridines find applications across various therapeutic domains, encompassing antimicrobial agents, anticancer agents, [12] antioxidants, antihypertensive, and more. [13][14][15][16][17][18][19] Furthermore, incorporating a fluorine atom into the phenolic group enhances reactivity, rendering it more effective as a nucleophile in reactions like methylation and glucuronidation. [20] On another front, the piperidine structural motif emerges as a promising candidate in drug discovery, holding considerable potential as an anticancer agent.…”

“…Nitrogen‐containing heterocycles, exemplified by pyridine and dihydropyridine ring systems, substantially influence drug functionality and interactions, enhancing attributes such as efficacy, stability, tissue permeability, and protein‐binding affinity [11] . Dihydropyridines find applications across various therapeutic domains, encompassing antimicrobial agents, anticancer agents, [12] antioxidants, antihypertensive, and more [13–19] …”