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Investigation of platelet aggregation inhibitory activity by phenyl amides and esters of piperidinecarboxylic acids.

Abstract：

:A series of anilides and phenyl esters of piperidine-3-carboxylic acid (nipecotic acid) were synthesized and tested for the ability to inhibit aggregation of human platelet rich-plasma triggered by adenosine 5'-diphosphate (ADP) and adrenaline. As a rule, amides were about two times more active than the corresponding esters, and derivatives bearing substituents at the para position of the phenyl ring were significantly more active than the meta-substituted ones. Among the tested compounds, 4-hexyloxyanilide of nipecotic acid (18a) was found to be the most active one, its IC(50) value being close to that of the most active bis-3-carbamoylpiperidines reported in literature (ca. 40 micro M) and aspirin (ca. 60 microM) in ADP- and adrenaline-induced aggregation, respectively. Compared with the isomeric 4-hexyloxyanilides of piperidine-2-carboxylic (pipecolinic) and piperidine-4-carboxylic (isonipecotic) acids, compound 18a showed higher activity, and a Hansch-type quantitative structure-activity relationship (QSAR) study highlighted lipophilicity and increase in electron density of the phenyl ring as the properties which mainly increase the antiplatelet activity (r(2)=0.74, q(2)=0.64). The interaction of nipecotoyl anilides with phosphatidylinositol, a major component of the inner layer of the platelet membranes, was investigated by means of flexible docking calculation methods to give an account of a key event underlying their biological action.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

de Candia M,Summo L,Carrieri A,Altomare C,Nardecchia A,Cellamare S,Carotti A

doi

10.1016/s0968-0896(02)00599-0

subject

Has Abstract

pub_date

2003-04-03 00:00:00

pages

1439-50

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968089602005990

journal_volume

11

pub_type

杂志文章

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