SOS Author Spotlight: Philip Harris (Pyrido[1,2-α]indoles)

Latest update to SOS includes synthetic routes to important hetarene systems: pyrido[1,2-α]indoles and aza analogues

 

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The content of Science of Synthesis has recently been supplemented with a series of chapters by Dr. Philip A. Harris (PA, U.S.A) on the major strategies for the preparation of a variety of hetarene structures based on the pyrido[1,2-α]indole motif. The scope covers benzo-fused derivatives, and also extends to separate chapters covering azapyrido[1,2-α]indoles (which feature an additional nitrogen atom as part of the ring system).

Pyrido[1,2-α]indoles and azapyrido[1,2-α]indoles are important structural motifs found in a number of biologically active polycyclic indole alkaloids. Substituted pyrido[1,2-α]indoles can also be highly fluorescent, displaying acid-responsive photoluminescence, and can form the core structures of organic semiconductors. Their intriguing structural features and the biological significance of the natural products containing a pyrido[1,2-α]indole unit have led to the development of multiple strategies for their synthesis.

 

Some Biologically Active Alkaloids Containing the Pyrido[1,2-α]indole Unit:

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Dr. Harris was able to draw on his experience from working in the pharmaceutical industry (GlaxoSmithKline) to add key perspectives. The reviews, which comprise 192 pages and include over 160 schemes, were edited by heterocyclic chemistry expert John A. Joule, Emeritus Professor at the University of Manchester, and form part of Volume 10 (Fused Five-Membered Hetarenes with One Heteroatom) in the Science of Synthesis series.


Direct links to the individual chapters can be found below:

10.24 Pyrido[1,2-a]indoles and Azapyrido[1,2-a]indoles (Introduction)
10.24.1 Pyrido[1,2-a]indoles and Related Benzo-Fused Ring Systems
10.24.2 Pyrimido[1,2-a]indoles and Related Benzo-Fused Ring Systems
10.24.3 Pyrimido[1,6-a]indoles and Related Benzo-Fused Ring Systems
10.24.4 Pyrazino[1,2-a]indoles and Related Benzo-Fused Ring Systems
10.24.5 Pyridazino[1,6-a]indoles and Related Benzo-Fused Ring Systems

 

Within each chapter, the synthetic methods are organized in a systematic way based on the type of transformation that leads to the hetarene system: by ring-closure reactions (further subdivided based on which bonds are formed in the ring-closure process), by ring transformation, or by substituent modification (cross-coupling reactions, electrophilic substitution, etc.).

Author Biography

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Philip Harris recently completed a 27-year career as a medicinal chemist at GlaxoSmithKline centered around primarily kinase inhibitor research. He was a member of drug discovery teams that resulted in two current oncology drugs: Votrient (VEGFR inhibitor, renal cancer) and Tafinlar (b-Raf inhibitor, melanoma). Philip is currently a medicinal chemistry consultant.

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