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제125회 대한화학회 학술발표회 및 총회 Synthetic approaches to a chemical library of azacyclic compounds via DDQ-mediated oxidative cyclization

2020년 2월 5일 21시 52분 32초
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Medicinal Chemistry
저자 및
Seungri Yoon, Sun-Joon Min1,*
Department of Applied Chemistry, Hanyang University, Korea
1Dept of Chemical & Molecular Eng/Applied Chemistry, Hanyang University, Korea
Azaspirocycles are spiro-connected bicyclic ring compounds containing nitrogen atom. In current drug discovery, they are considered as core structures of pharmaceutics and medicinally valuable molecules. They are also found in many biologically active natural products. For example, histrionicotoxin (HTX) analogues, a kind of alkaloids isolated from the skins of the brightly‐colored “poison dart” frogs of Central America, contain an essential azaspirocycle core and possess activity as a noncompetitive blocker of nicotinic acetylcholine receptors. Perhydrohistrionicotoxin also has significant biological activities involved in regulation of neuromuscular transmission. Thus, the development of effective synthetic methods to construct crucial azaspirocyclic structures is of considerable importance and highly challenging. In this study, we attempted to synthesize azaspirocycles via both inter- and intramolecular C-C bond formations using DDQ as a key oxidant for C-H activation. The key steps are involved in oxidative allylation of tetrahydroisoqunoline with allylsilanes, followed by oxidative Mannich or aza-Prins type reactions. Our current effort to explore reaction optimization will be described in this presentation.