The Antileukotrienic Derivatives and Homologues of [(Quinolin-2-ylmethoxy)sulfanyl]benzoic Acids with Reduced Lipophilicity

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Title:The Antileukotrienic Derivatives and Homologues of [(Quinolin-2-ylmethoxy)sulfanyl]benzoic Acids with Reduced Lipophilicity
Creators:
Kuchař, Miroslav
Brunová, Bohumila
Junek, Richard
Rodling, Robert
Hájíček, Josef
Panajotová, Vladimíra
Jandera, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 9, pp. 1357-1371
Uncontrolled Keywords:Lipophilicity, FLAP inhibition, Regression analysis, Arylacetic acids, Antileukotrienic activities, [(Phenylsulfanyl)phenyl]acetic acids, Quinolines, Antiasthmatic effect

Abstract

A series of ({[(quinolin-2-ylmethoxy)phenyl]sulfanyl}phenyl)acetic acids <strong>2</strong> and <i>S</i>-oxidized derivatives of {[(quinolin-2-ylmethoxy)phenyl]sulfanyl}benzoic acids <strong>3</strong> were prepared and their antileukotrienic and antiasthmatic activities evaluated. Regression analysis led to the conclusion that the antileukotrienic activities of compounds <strong>2</strong> correspond to the relationships between these activities and lipophilicity, derived for the previously synthesized series of substituted (arylsulfanyl)benzoic acids <strong>1A</strong>, <strong>1B</strong> and <strong>1C</strong>. Acids <strong>3</strong> are outliers from these relationships, probably due to a somewhat different mechanism of action. A higher antiasthmatic activity was observed in some [(arylsulfanyl)phenyl]acetic acids <strong>2</strong> in comparison with the corresponding analogs bearing the (arylsulfanyl)benzoic acid moiety. The inhibition of 5-lipoxygenase activated protein (FLAP) was determined for these compounds, and the influence of the direct inhibition of LTB<sub>4</sub> biosynthesis is discussed to explain the differences in the antiasthmatic effect of the compounds under study. <p>

Title:The Antileukotrienic Derivatives and Homologues of [(Quinolin-2-ylmethoxy)sulfanyl]benzoic Acids with Reduced Lipophilicity
Creators:
Kuchař, Miroslav
Brunová, Bohumila
Junek, Richard
Rodling, Robert
Hájíček, Josef
Panajotová, Vladimíra
Jandera, Antonín
Uncontrolled Keywords:Lipophilicity, FLAP inhibition, Regression analysis, Arylacetic acids, Antileukotrienic activities, [(Phenylsulfanyl)phenyl]acetic acids, Quinolines, Antiasthmatic effect
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:9
Page Range:pp. 1357-1371
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051357UNSPECIFIED
ID Code:2416
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Kuchař, Miroslav; Brunová, Bohumila; Junek, Richard; Rodling, Robert; Hájíček, Josef; Panajotová, Vladimíra; Jandera, Antonín (2005) The Antileukotrienic Derivatives and Homologues of [(Quinolin-2-ylmethoxy)sulfanyl]benzoic Acids with Reduced Lipophilicity. Collection of Czechoslovak Chemical Communications, 70 (9). pp. 1357-1371. ISSN 0010-0765

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