62553-86-0

Basic information

• Product Name: 3-hydroxy-N-(3-methoxyphenyl)-2-Naphthalenecarboxamide
• Synonyms: 3-hydroxy-N-(3-methoxyphenyl)-2-Naphthalenecarboxamide;3-hydroxy-N-(3-methoxyphenyl)naphthalene-2-carboxamide;3-Hydroxy-N-(3-methoxyphenyl)-2-naphthamide;2-Naphthalenecarboxamide, 3-hydroxy-N-(3-methoxyphenyl)-
• CAS NO: 62553-86-0
• Molecular Formula: C₁₈H₁₅NO₃
• Molecular Weight: 293.3166
• Mol File: 62553-86-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-hydroxy-N-(3-methoxyphenyl)-2-Naphthalenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-N-(3-methoxyphenyl)-2-Naphthalenecarboxamide(62553-86-0)
• EPA Substance Registry System: 3-hydroxy-N-(3-methoxyphenyl)-2-Naphthalenecarboxamide(62553-86-0)

Safety Data

• Hazardous Substances Data: 62553-86-0(Hazardous Substances Data)

Upstream product

• 536-90-3 m-Anisidine 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 591-27-5 m-Hydroxyaniline 

Relevant articles and documents

3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity

Abstract: Series of ring-substituted 3-hydroxynaphthalene-2-carboxanilides were screened for their in vitro activity against wild-type S427 (bloodstream form) of Trypanosoma brucei brucei. 3-Hydroxy-N-(3-trifluoromethylphenyl)- and 3-hydroxy-N-(4-trifluoromethylphenyl)naphthalene-2-carboxamides showed the highest biological activity (MIC?=?1.56 and 2.08?μmol/dm3, respectively). Antitrypanosomal activity was correlated with the experimentally determined lipophilicity and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pKa T value was found to be ca. 7.5. The structure–activity relationships of all compounds are discussed. Graphical abstract: [Figure not available: see fulltext.].

Antimycobacterial N-alkoxyphenylhydroxynaphthalenecarboxamides affecting photosystem II

N-(Alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides (series A) and N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides (series B) affecting photosystem (PS) II inhibited photosynthetic electron transport (PET) in spinach chloroplasts. Their inhibitory activity depended on the compound lipophilicity as well as on the position of the alkoxy substituent. The most potent PET inhibitors were 2-hydroxy-N-phenylnaphthalene-1-carboxamide and N-[3-(but-2-yloxy)phenyl]-2-hydroxynaphthalene-1-carboxamide within series A (IC50?=?28.9 and 42.5?μM, respectively) and 1-hydroxy-N-(3-propoxyphenyl)naphthalene-2-carboxamide and 1-hydroxy-N-(3-ethoxyphenyl)-naphthalene-2-carboxamide (IC50?=?2.0 and 3.1?μM, respectively) within series B. The inhibitory activity of C′(3) or C′(4) alkoxy substituted compounds of series B was considerably higher than that of C′(2) ones within series A. The PET-inhibiting activities of both series were compared with the PET inhibition of isomeric N-alkoxyphenyl-3-hydroxynaphthalene-2-carboxamides (series C) reported recently. Interactions of the studied compounds with chlorophyll a and aromatic amino acids present in pigment–protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P680 and plastoquinone QB in the PET chain occurring on the acceptor side of PS?II can be suggested as the site of action of the compounds.

Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides

In this study, a series of twenty-two ring-substituted 3-hydroxy- Nphenylnaphthalene- 2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 μmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2- carboxamide showed higher activity (MIC = 28.4 μmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2- carboxamide expressed higher activity (MIC = 13.0 μmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.