Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones

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Title:Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones
Creators:
Waisser, Karel
Macháček, Miloš
Dostál, Hynek
Gregor, Jiří
Kubicová, Lenka
Klimešová, Věra
Kuneš, Jiří
Palát, Karel
Hladůvková, Jana
Kaustová, Jarmila
Möllmann, Ute
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 11, pp. 1902-1924
Uncontrolled Keywords:QSAR, Cosine coefficient, Antimicrobial activity, Anthranilanilides, Salicylanilides, Quinazolines, 1,3-Benzoxazines, Tuberculostatics

Abstract

A series of 3-phenyl-2<i>H</i>-1,3-benzoxazine-2,4(3<i>H</i>)-diones <strong>2</strong> and 3-phenylquinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones <strong>5</strong> substituted on the phenyl rings were synthesized. The target compounds as well as the intermediates were tested against <i>Mycobacterium tuberculosis, M. kansasii</i>, and <i>M. avium</i>. The replacement of the oxygen atom by nitrogen resulted in a decrease or loss of antimycobacterial activity. 2-[(Ethoxycarbonyl)amino]benzanilides <strong>4</strong> appeared to be inactive. Salicylanilides <strong>1</strong> and 3-phenyl-2<i>H</i>-1,3-benzoxazine-2,4(3<i>H</i>)-diones <strong>2</strong> exhibit significant activity against both <i>M. tuberculosis</i> and nontuberculous mycobacteria (the MICs within the range of 4-250 μmol/l for all compounds). The antimycobacterial activity of the compounds increases with increasing both electron-withdrawing properties and hydrophobicity of the substituent(s) on the phenyl moiety. The antimycobacterial profile of the compounds was analyzed according to the criteria based on vector algebra, such as cosine coefficients. Moreover, salicylanilides <strong>1</strong> exhibit activity against other microorganisms tested by the agar diffusion method. <p>

Title:Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones
Creators:
Waisser, Karel
Macháček, Miloš
Dostál, Hynek
Gregor, Jiří
Kubicová, Lenka
Klimešová, Věra
Kuneš, Jiří
Palát, Karel
Hladůvková, Jana
Kaustová, Jarmila
Möllmann, Ute
Uncontrolled Keywords:QSAR, Cosine coefficient, Antimicrobial activity, Anthranilanilides, Salicylanilides, Quinazolines, 1,3-Benzoxazines, Tuberculostatics
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:64
Number:11
Page Range:pp. 1902-1924
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991902UNSPECIFIED
ID Code:1604
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:11

Citation

Waisser, Karel; Macháček, Miloš; Dostál, Hynek; Gregor, Jiří; Kubicová, Lenka; Klimešová, Věra; Kuneš, Jiří; Palát, Karel; Hladůvková, Jana; Kaustová, Jarmila; Möllmann, Ute (1999) Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones. Collection of Czechoslovak Chemical Communications, 64 (11). pp. 1902-1924. ISSN 0010-0765

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