Antimycobacterial and herbicidal activity of ring-substituted 1-hydroxynaphthalene-2-carboxanilides
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- 作者：Tomas Gonec ; Jiri Kos ; Iveta Zadrazilova ; Matus Pesko ; Stanislava Keltosova ; Jan Tengler ; Pavel Bobal ; Peter Kollar ; Alois Cizek ; Katarina Kralova ; Josef Jampilek
- 关键词：Hydroxynaphthalene-2-carboxanilides ; Lipophilicity ; Photosynthetic electron transport inhibition ; Spinach chloroplasts ; In vitro antimycobacterial activity ; In vitro cytotoxicity ; Structure&ndash ; activity relationships
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2013
- 出版时间：1 November, 2013
- 年：2013
- 卷：21
- 期：21
- 页码：6531-6541
- 全文大小：602 K
文摘
In this study, a series of 22 ring-substituted 1-hydroxynaphthalene-2-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium marinum, Mycobacterium kansasii and Mycobacterium smegmatis. The compounds were also tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Most of tested compounds showed the antimycobacterial activity against the three strains comparable or higher than the standard isoniazid. N-(3-Fluorophenyl)-1-hydroxynaphthalene-2-carboxamide showed the highest biological activity (MIC = 28.4 ¦Ìmol/L) against M. marinum, N-(4-fluorophenyl)-1-hydroxynaphthalene-2-carboxamide showed the highest biological activity (MIC = 14.2 ¦Ìmol/L) against M. kansasii, and N-(4-bromophenyl)-1-hydroxynaphthalene-2-carboxamide expressed the highest biological activity (MIC = 46.7 ¦Ìmol/L) against M. smegmatis. This compound and 1-hydroxy-N-(3-methylphenyl)naphthalene-2-carboxamide were the most active compounds against all three tested strains. The PET inhibition expressed by IC50 value of the most active compound 1-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-2-carboxamide was 5.3 ¦Ìmol/L. The most effective compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. For all compounds, structure-activity relationships are discussed.