Synthesis and Prediction of the Ubiquinol‐cytochrome c Reductase Inhibitory Activity of 3,4‐Dihydroisoquinolines and 2‐Azaspiro[4.5]decanes (Spiropyrrolines)

Abstract

Isoquinolines rank as the second largest group among the plant alkaloids. Natural isoquinolines and synthetic isoquinoline derivatives exhibit numerous biological activities. In this study, the approaches to synthesis of new 3,4‐dihydroisoquinoline and 2‐azaspiro[4.5]decane (spiropyrroline) derivatives annelated by C(3)─C(4) bonds with a cyclohexyl or cyclopentyl moiety have been developed. In accord with the results of biological activity prediction by the pass software, molecular docking was carried out on the ubiquinol‐cytochrome c reductase (bc1 complex) model. Compounds 6e and 12a,d were found out as potential Q0 site inhibitors of the bovine bc1 complex.

Metal-free dearomatization reactions of naphthol-ynamides for the divergent and enantioselective synthesis of azaspirocycles

“…1). 1 Due to the relatively congested quaternary carbon center, it is a highly challenging task for chemists to develop a synthetically applicable methodology for synthesizing them. 2 Thus, the development of efficient, mild, and streamlined synthetic routes continues to be in high demand in the organic synthetic community, especially asymmetric synthesis.…”

“…These two spirocyclic scaffolds are important structural motifs that contain broad application prospects. 1,17 Moreover, such a CADA reaction is also achieved by employing chiral Brønsted acids as catalysts.…”

Controllable cyclization of alkynyl thioethersviaBrønsted acid-catalyzed dearomatization

“…Remarkably, phenanthrol derivatives such as gymnopusin, fimbriol, erianthridin and so on play a vital role in medical and pharmaceutical industries. 11 In contrast to the vinyl cation intermediates that exist in the traditional Brønsted acid-catalyzed alkynyl hydroarylation, this reaction is mediated by unprecedented and valuable dearomative spirocyclic intermediates, 12 which can also be controllably synthesized from the same alkynyl thioethers by just adjusting the Brønsted acid catalyst. Moreover, a catalytic asymmetric dearomatization reaction is realized with moderate enantioselectivity by employing chiral phosphoric acid (CPA).…”