Background and overview of application examples of 6-aminopyridineboronic acid
6-Aminopyridineboronic acid is a boronic acid derivative of bromopyridine. Boronic acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In the Suzuki coupling, aryl halides and aryl or vinyl borates or boronic acids are coupled using Pd(PPh3)4. 6-Aminopyridineboronic acid can be prepared from benzophenone and 2-amino-5-bromopyridine first, 5-bromo-N-(diphenylmethylene)-2-pyridinamine, and then reacted with boric acid through butyllithium as a base. It is obtained by deprotecting triisopropyl ester after reaction.
Application examples of 6-aminopyridineboronic acid
6-Aminopyridineboronic acid can be used to prepare IRAK4 inhibitors with the following structure. IRAK4 is recognized as an important pharmacological target for the treatment of chronic inflammatory diseases. It is a ubiquitously expressed serine/threonine kinase that is directly involved in innate inflammatory signaling downstream of the Toll-like receptor (TLR) and interleukin 1 (IL-1) receptor families. Selective small molecule inhibitors of IRAK4 may have therapeutic value in treating cytokine-driven autoimmune diseases while avoiding extensive immunosuppressive side effects. Additionally, recent studies suggest that targeting IRAK4 may be useful in other inflammatory pathologies, such as atherosclerosis and diffuse large B-cell lymphoma. Therefore, inhibitors of IRAK4 kinase activity are potential therapies for a variety of diseases caused by cyanobenzene borates, such as autoimmune diseases, inflammation, cardiovascular diseases, cancer, and metabolic diseases.
References
[1] [Chinese invention, Chinese invention authorization] CN201480025409.7 Method for preparing aminoarylboronic acid, aminoheteroarylboronic acid and ester
[2] From PCT Int. Appl., 2020106059, 28 May 2020
