439614-63-8Relevant academic research and scientific papers
Optimized palladium-based approaches to analogues of PK 11195
Guillou, Sandrine,Janin, Yves L.
experimental part, p. 1377 - 1384 (2009/04/07)
(Chemical Equation Presented) The peripheral-type benzodiazepine receptor ligands such as PK 11195 and Ro 5-4864 were found more than twenty years ago in the course of research on neurobiology. These ligands were instrumental in pointing out an involvement of the peripheral-type benzodiazepine receptor (PBR) in apoptosis processes. With in mind an improvement of the solubility of PK 11195 in biological media, we report here improved reaction conditions for the palladium-based arylation reaction of alkyl 1-bromoisoquinoline-3-carboxylates and its ethyl 4-bromoquinoline-2-carboxylate isomer. The use of [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium as a precatalyst enabled a much improved preparation of an array of the 1-arylisoquinoline-3- carboxylates as well as 4-arylquinoline-3-carboxylates. This work should pave the way for the design of chemical probes aiming at the elucidation of the PBR biological role(s).
A novel approach for the synthesis of the peripheral benzodiazepine receptor ligand, PK11195
Stevenson, Louise,Pimlott, Sally L.,Sutherland, Andrew
, p. 7137 - 7139 (2008/03/11)
A new synthesis of the peripheral benzodiazepine receptor ligand, PK11195 has been developed in only six-steps using a Heck-type reaction and a Suzuki coupling to effect the key transformations. The flexibility of this new approach is demonstrated by the
Synthetic approaches to 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid
Janin, Yves L.,Roulland, Emmanuel,Beurdeley-Thomas, Arnaud,Decaudin, Didier,Monneret, Claude,Poupon, Marie-France
, p. 529 - 532 (2007/10/03)
In connection with our research of new antitumor compounds, previously undescribed approaches to the 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid 9 are reported here. Two related accesses from phenylethylamine or amphetamine were investigated and were found to be successful. A more robust synthesis, using Suzuki's cross-coupling between 2-chlorophenylboronic acid 15 and the previously unreported methyl-1-bromoisoquinoline-3-carboxylate 14 was also developed. This synthetic route provides the ground for a combinatorial approach to the core structure of new potential peripheral benzodiazepine receptor ligands.
