On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides

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Title:On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides
Creators:
Waisser, Karel
Peřina, Milan
Klimešová, Věra
Kaustová, Jarmila
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 7, pp. 1275-1294
Uncontrolled Keywords:Tuberculostatic, QSAR, Free-Wilson method, Antituberculotics, Antimicrobial activity, Structure-activity relationships, Salicylamides, Substituent effects

Abstract

Sixty-six <i>N</i>-benzylsalicylamides substituted in the acyl moiety in positions 3, 4 or 5 and in position 4 on the benzylic aromatic ring were synthesized. The compounds were tested for <i>in vitro</i> antimycobacterial activity against <i>Mycobacterium tuberculosis</i>, <i>Mycobacterium kansasii</i> and <i>Mycobacterium avium</i>. To evaluate structure-antimycobacterial activity relationships (QSARs), approaches based on the Free-Wilson as well as a combination of the Free-Wilson and Hansch methods were employed (substituent constants were used to describe the influence of the benzyl substituents, indicator parameters were used for the substituents on the acyl moiety). The use of the Hammett constants for benzyl substituents was not important for QSAR equations. The quadratic representation of lipophilicity parameters (π<sup>2</sup>) was significant only in QSAR equations of antimycobacterial activity against <i>M. avium</i>. <p>

Title:On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides
Creators:
Waisser, Karel
Peřina, Milan
Klimešová, Věra
Kaustová, Jarmila
Uncontrolled Keywords:Tuberculostatic, QSAR, Free-Wilson method, Antituberculotics, Antimicrobial activity, Structure-activity relationships, Salicylamides, Substituent effects
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:68
Number:7
Page Range:pp. 1275-1294
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031275UNSPECIFIED
ID Code:2119
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Waisser, Karel; Peřina, Milan; Klimešová, Věra; Kaustová, Jarmila (2003) On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides. Collection of Czechoslovak Chemical Communications, 68 (7). pp. 1275-1294. ISSN 0010-0765

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