687974-93-2Relevant academic research and scientific papers
Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors
Tong, Yuan Feng,Zhang, Pei,Chen, Feng,Hao, Ling Hua,Ye, Fei,Tian, Jin Ying,Wu, Song
, p. 1415 - 1418 (2011/10/09)
Based on the fact that petroselinic acid showed good inhibitory activity (IC50=6.99μmol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106nmol/L in vitro.
Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides
De Marco, Agostino,De Candia, Modesto,Carotti, Andrea,Cellamare, Saverio,De Candia, Erica,Altomare, Cosimo
, p. 153 - 164 (2007/10/03)
Using N-[4-(hexyloxy)phenyl]piperidine-3-carboxamide (17c) as a structural lead, a number of isomers, derivatives, and ring-opened analogs were synthesized and tested for their ability to block the in vitro aggregation of human platelets induced by adenosine 5′-diphosphate (ADP). For the most active compounds, inhibition of the platelet aggregation triggered by arachidonic acid (AA) and ADP-induced intraplatelet calcium mobilization was also demonstrated. Based on quantitative structure-activity relationships (QSARs), we proved the impact of hydrophobicity on antiplatelet activity by a nonlinear (parabolic or bilinear) relationship between pIC50 and lipophilicity, as assessed by RP-HPLC capacity factors and Clog P (i.e. calculated 1-octanol-water partition coefficients). This study highlighted the following additional SARs: quasi-isolipophilic isomers of 17c (isonipecotanilides and pipecolinanilides) and ring-opened analogs (e.g. anilide of β-alanine) exhibited lower antiplatelet activity; methylation of the piperidine nitrogen of 17c has no effect, whereas alkylation with an n-propyl group decreases the activity by a factor of approximately 2, most likely due to a conformation-dependent decrease in lipophilicity.
