169774-59-8Relevant articles and documents
Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands
Zanato, Chiara,Watson, Sonia,Bewick, Guy S.,Harrison, William T. A.,Zanda, Matteo
supporting information, p. 9638 - 9643 (2015/02/19)
(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. This journal is
Method for the preparation of N-substituted 4-ketoproline derivatives
-
, (2008/06/13)
Method for the preparation of N-protected 4-ketoproline derivatives of formula I STR1 by oxidation of the corresponding N-protected 4-hydroxyproline derivatives of STR2 using the system TEMPO (2,2,6,6-tetramethylpiperidinyl oxy free radical)/NaOCl.
A versatile approach to acromelic acid analogues
Baldwin, Jack E.
, p. 4869 - 4872 (2007/10/02)
A route to acromelic acid analogues and their corresponding C-4 epimers from trans-4-hydroxy-L-proline is described. The C-4 substituent was introduced by a Suzuki-type boronate coupling to a vinyl triflate.