Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
10588608 | Bioorganic & Medicinal Chemistry Letters | 2011 | 4 Pages |
Abstract
Conformational modulation of the aryl portion of a set of N,N-bis(cyclohexanol)amine aryl esters (1a-d) that are potent Pgp-dependent MDR inhibitors has been performed. Toward this end the trans-3-(3,4,5-trimethoxyphenyl)acrylic acid present in set 1 was substituted with 3-(3,4,5-trimethoxyphenyl)propanoic and 3-(3,4,5-trimethoxyphenyl)propiolic moieties to give sets 2 and 3, respectively. While the introduction of 3-(3,4,5-trimethoxyphenyl)propanoic moiety resulted in a definite drop in potency and efficacy, esterification with 3-(3,4,5-trimethoxyphenyl)propiolic acid gave four isomers (3a-d) that maintain high potency and possess optimal efficacy. These results are discussed in terms of conformational flexibility of the different sets of compounds.
Keywords
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Cecilia Martelli, Silvia Dei, Catherine Lambert, Dina Manetti, Francesca Orlandi, Maria Novella Romanelli, Serena Scapecchi, Milena Salerno, Elisabetta Teodori,