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Studies on calpain inhibitors. Synthesis of partially reduced isoquinoline-1-thione derivatives and conversion to functionalized 1-chloroisoquinolines

AuthorsChicharro, Roberto ; Alonso Giner, Mercedes; Arán, Vicente J. ; Herradón García, Bernardo
KeywordsCalpain inhibitor
Issue Date9-Feb-2008
CitationTetrahedron Letters 49(14): 2275-2279 (2008)
AbstractSequential treatment of a (3-substituted-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene)acetic acid with thionyl chloride and a nucleophile did not give the expected ester or amide, but a derivative of 2-(3-substituted-1-chloroisoquinolin-4-yl)acetic acid, constituting a simple procedure for the synthesis of functionalized 1-chloroisoquinolines, which can be useful synthetic intermediates. The different reactivity between lactams and thiolactams has been computationally modelled. The activity as calpain inhibitors of both thiolactams and chloroisoquinoline has been measured, finding that some of these compounds are inhibitors in the micromolar range.
Description5 pages, 2 figures, 5 schemes.-- Printer version published Mar 31, 2008.-- Taken in part from the Ph.D. of R.C. (UAM, Madrid, 2007) and the projected Ph.D. of M.A.
Supporting information available: Experimental details of synthetic procedures, spectroscopic and analytical data for new compounds and full computational results (18 pages).
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2008.02.023
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