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.

Inhibition of P-glycoprotein-mediated Multidrug Resistance (MDR) by N,N-bis(cyclohexanol)amine aryl esters: further restriction of molecular flexibility maintains high potency and efficacy / Martelli, Cecilia; Dei, Silvia; Lambert, C.; Manetti, Dina; Orlandi, Francesca; Romanelli, MARIA NOVELLA; Scapecchi, Serena; Salerno, M.; Teodori, Elisabetta. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - STAMPA. - 21:(2011), pp. 106-109. [10.1016/j.bmcl.2010.11.059]

Inhibition of P-glycoprotein-mediated Multidrug Resistance (MDR) by N,N-bis(cyclohexanol)amine aryl esters: further restriction of molecular flexibility maintains high potency and efficacy

MARTELLI, CECILIA;DEI, SILVIA;MANETTI, DINA;ORLANDI, FRANCESCA;ROMANELLI, MARIA NOVELLA;SCAPECCHI, SERENA;TEODORI, ELISABETTA
2011

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.
2011
21
106
109
Martelli, Cecilia; Dei, Silvia; Lambert, C.; Manetti, Dina; Orlandi, Francesca; Romanelli, MARIA NOVELLA; Scapecchi, Serena; Salerno, M.; Teodori, Elisabetta
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/401505
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