ArticleMolecules (Basel, Switzerland)2016
N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity.
Article in Molecules (Basel, Switzerland), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Insight into antistaphylococcal effect of chlorinated 1-hydroxynaphthalene-2-carboxanilides.ADMET & DMPK · 2025Article
- Antimicrobial and ADME properties of methoxylated, methylated and nitrated 2-hydroxynaphthalene-1 carboxanilides.ADMET & DMPK · 2025Article
- Design, Synthesis and Antimicrobial Properties of New Tetracyclic Quinobenzothiazine Derivatives.International journal of molecular sciences · 2022Article
- Insights into Antimalarial Activity ofMolecules (Basel, Switzerland) · 2022Article
- Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates.Pharmaceuticals (Basel, Switzerland) · 2022Article
- Study of Biological Activities and ADMET-Related Properties of Novel ChlorinatedInternational journal of molecular sciences · 2022Article
- Consensus-Based Pharmacophore Mapping for New Set ofInternational journal of molecular sciences · 2020Article
- Identification of Substituted Amino Acid Hydrazides as Novel Anti-Tubercular Agents, Using a Scaffold Hopping Approach.Molecules (Basel, Switzerland) · 2020Article
- Ring-Substituted 1-Hydroxynaphthalene-2-Carboxanilides Inhibit Proliferation and Trigger Mitochondria-Mediated Apoptosis.International journal of molecular sciences · 2020Article
- Bioactivity of Methoxylated and Methylated 1-Hydroxynaphthalene-2-Carboxanilides: Comparative Molecular Surface Analysis.Molecules (Basel, Switzerland) · 2019Article
- Design and synthesis of anticancer 1-hydroxynaphthalene-2-carboxanilides with a p53 independent mechanism of action.Scientific reports · 2019Article
- Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.International journal of molecular sciences · 2018Article
- Investigation of Hydro-Lipophilic Properties ofMolecules (Basel, Switzerland) · 2018Article
- Proline-Based Carbamates as Cholinesterase Inhibitors.Molecules (Basel, Switzerland) · 2017Article
- Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II.Molecules (Basel, Switzerland) · 2017Article
- Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates.Molecules (Basel, Switzerland) · 2017Article
- Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates.Molecules (Basel, Switzerland) · 2016Article
Corrections and comments
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Authors and funding
11 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A series of nineteen N-(alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides and a series of their nineteen positional isomers N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides were prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, M. kansasii and M. smegmatis. Screening of the cytotoxicity of the compounds was performed using human monocytic leukemia THP-1 cells. Some of the tested compounds showed antimycobacterial activity comparable with or higher than that of rifampicin. For example, 2-hydroxy-N-(4-propoxyphenyl)-naphthalene-1-carboxamide showed the highest activity (MIC = 12 µM) against M. tuberculosis with insignificant cytotoxicity. N-[3-(But-2-yloxy)phenyl]- and N-[4-(but-2-yloxy)phenyl]-2-hydroxy-naphthalene-1-carboxamide demonstrated high activity against all tested mycobacterial strains and insignificant cytotoxicity. N-(Alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides demonstrated rather high effect against M. smegmatis and M. kansasii and strong antiproliferative effect against the human THP-1 cell line. Lipophilicity was found as the main physicochemical parameter influencing the activity. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) assay. Structure-activity relationships are discussed.
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