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Título

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

AutorChicharro, Roberto ; Alonso Giner, Mercedes; Arán, Vicente J. ; Herradón García, Bernardo
Palabras claveCalpain inhibitor
Chloroisoquinoline
Lactam
Thiolactam
Fecha de publicación9-feb-2008
EditorElsevier
CitaciónTetrahedron Letters 49(14): 2275-2279 (2008)
ResumenSequential 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.
Descripción5 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).
Versión del editorhttp://dx.doi.org/10.1016/j.tetlet.2008.02.023
URIhttp://hdl.handle.net/10261/11325
DOI10.1016/j.tetlet.2008.02.023
ISSN0040-4039
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