Advances in the chemistry of tetrahydroquinolines.

Potassium channels participate in many critical biological functions and play important roles in a variety of diseases. In recent years, many significant discoveries have been made which motivate us to review these achievements. The focus of our review is mainly on three aspects. Firstly, we try to summarize the latest developments in structure determinants and regulation mechanism of all types of potassium channels. Secondly, we review some diseases induced by or related to these channels. Thirdly, both qualitative and quantitative approaches are utilized to analyze structural features of modulators of potassium channels. Our analyses further prove that modulators possess some certain natural-product scaffolds. And pharmacokinetic parameters are important properties for organic molecules. Besides, with in silico methods, some features that can be used to differentiate modulators are derived. There is no doubt that all these studies on potassium channels as possible pharmaceutical targets will facilitate future translational research. All the strategies developed in this review could be extended to studies on other ion channels and proteins as well.

Potassium Channels: Structures, Diseases, and Modulators

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.200790236

Total synthesis of the potent antitumor macrolides pladienolide B and D.

Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2006.

History, biology and chemistry of Mycobacterium ulcerans infections (Buruli ulcer disease)

A practical synthesis of a tetrahydroaminoquinoline scaffold (12) was developed that used a stereocontrolled aza Michael as the key reaction. Three tetrahydroquinoline alkaloid-like, tricyclic derivatives 16, 18, and 19 with different medium to macrocyclic ring skeletons were obtained, using this scaffold as the starting material, in a modular manner. The macrocyclic compounds with an isolated olefin and an electron-deficient olefin were obtained by ring-closing metathesis approaches. Compounds 16 and 18 are unique and contain bridged 10- and 12-membered functionalized rings. The NMR studies of these compounds revealed interesting information on the conformation of the bicyclic scaffolds that was dependent on the nature and the size of the macrocyclic rings. Finally, this modular methodology, using compound 21 anchored onto the solid support, successfully led to the generation of different macrocyclic derivatives, 23, 25, and 27 in solid-phase synthesis. The solid-phase synthesis approach outlined in this article has the potential to generate tetrahydroquinoline-based tricyclic compounds containing different medium to macrocyclic architectures.

/pdf/part-1-modular-approach-to-obtaining-diverse-2pw3e8mpo6.pdf

Part 1. modular approach to obtaining diverse tetrahydroquinoline-derived polycyclic skeletons for use in high-throughput generation of natural-product-like chemical probes.

The solution- and solid-phase synthesis to obtain several natural-product-like, tetrahydroquinoline-based, polycyclic derivatives were developed. In one approach, two derivatives (38 and 41) having an eight-membered unsaturated lactam were successfully obtained both in solution and on solid support.

Part 2: building diverse natural-product-like architectures from a tetrahydroaminoquinoline scaffold. Modular solution- and solid-phase approaches for use in high-throughput generation of chemical probes.

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Part 1. modular approach to obtaining diverse tetrahydroquinoline-derived polycyclic skeletons for use in high-throughput generation of natural-product-like chemical probes.

Part 2: building diverse natural-product-like architectures from a tetrahydroaminoquinoline scaffold. Modular solution- and solid-phase approaches for use in high-throughput generation of chemical probes.