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A Method for Parallel Solid-Phase Synthesis of Iodinated Analogues of the CB1Receptor Inverse Agonist Rimonabant
Author(s) -
Alan C. Spivey,
ChihChung Tseng,
Teyr C. Jones,
Andrew D. Kohler,
George J. Ellames
Publication year - 2009
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol902038y
Subject(s) - inverse agonist , chemistry , rimonabant , agonist , inverse , phase (matter) , combinatorial chemistry , solid phase synthesis , receptor , stereochemistry , computational chemistry , organic chemistry , biochemistry , cannabinoid receptor , mathematics , peptide , geometry
A method for the parallel solid-phase synthesis (SPS) of iodinated analogues of Sanofi-Aventis' type 1 cannabinoid (CB1) receptor inverse agonist rimonabant (acomplia) has been developed. The method allows the synthesis of a range of C3 amide/hydrazide derivatives from a resin-bound C3 ester precursor. The C-Ge linkage to the Hypogel-200 resin is stable to the diversification conditions but allows ipso-iododegermylative cleavage using NaI/NCS even for the products containing the oxidatively labile hydrazide moiety.

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