Synthesis and Evaluation of Novel 2-Oxo-1,2-dihydro-3-quinolinecarboxamide Derivatives as Serotonin 5-HT4 Receptor Agonists.

5‐HT4 Receptor Ligands: Applications and New Prospects

“…As in the parent series, the pharmacological profile depended upon the nature of the substitution on the nitrogen atom of the benzimidazole ring: the compound 2 (R = cC3H5, R' = i-C3H7) was a selective ligand with 5-HT4 receptor antagonist activity (Ki = 6.7 nM, pKi = 7.78) and the compound 3 (R = i-C3H7, R' = Me) was a selective high partial agonist with moderate affinity (intrinsic activity = 0.94, Ki = 91.1 nM). More recently, 29 derivatives of 3quinolocarboxamide 4, a bioisosteric group of benzimidazolone, were synthesised as structural analogues of BIMU 8. Several potent and selective 5-HT4 receptor agonists were obtained by introducing various substituents on the nitrogen atom of the tropane ring.…”

“…TS-951K (4, R = OH, n = 3) was selected as a promising agent to alleviate symptoms of the gastrointestinal dysfunctions. 30…”

Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1H)-ones

“…Quinolin-2­(1 H )-ones are very important N -heterocycles and have drawn much attention because they can serve as versatile scaffolds and are found extensively in natural products, pharmaceutical molecules, and synthetic compounds . They display various pharmaceutical activities and have been utilized as antitumor, antiplatelet, and antibiotic agents as well as diverse receptor antagonists . Therefore, much effort has been put toward their preparation, and a variety of synthetic methods have been reported.…”

AlCl3-Mediated Synthesis of 4-Aryl-2-quinolone-3-carboxylates

“…1 More specifically, various biologically and pharmacologically significant compounds contain the 2-quinolone moiety as a structural and pharmacophoric feature, and these compounds exhibit a variety of functions, including anticancer activity, antiplatelet activity, glycine NMDA receptor antagonism, 5-HT 4 agonism, potassium channel opening activity, and antimicrobial activity. [2][3][4][5][6][7][8] Figure 1 Structure of 4-aryl-2-quinolone (1) Due to the chemical and medicinal importance of 4aryl-2-quinolones, a number of synthetic methods for their preparation have been investigated to date. Based on the cy-clization conditions employed, these synthetic methods can be divided into two categories, namely dehydrative cyclization and transition-metal-catalyzed cyclization.…”