13545-65-8

Basic information

• Product Name: 1-Hydroxy-N-phenyl-2-naphthalenecarboxamide
• Synonyms: 1-Hydroxy-N-phenyl-2-naphthalenecarboxamide
• CAS NO: 13545-65-8
• Molecular Formula: C₁₇H₁₃NO₂
• Molecular Weight: 263.29
• Mol File: 13545-65-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 391.8°C at 760 mmHg
• Flash Point: 190.7°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 1.07E-06mmHg at 25°C
• Refractive Index: 1.734
• CAS DataBase Reference: 1-Hydroxy-N-phenyl-2-naphthalenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-N-phenyl-2-naphthalenecarboxamide(13545-65-8)
• EPA Substance Registry System: 1-Hydroxy-N-phenyl-2-naphthalenecarboxamide(13545-65-8)

Safety Data

• Hazardous Substances Data: 13545-65-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H13NO2/c19-16-14-9-5-4-6-12(14)10-11-15(16)17(20)18-13-7-2-1-3-8-13/h1-11,19H,(H,18,20)

Upstream product

• 16323-15-2 N-Phenyl-O-p-chlorophenylcarbamate 
• 3019-88-3 sodium naphtholate 
• 108-88-3 toluene 
• 3759-61-3 1-naphthyl chloroformate 
• 103-72-0 phenyl isothiocyanate 
• 90-15-3 α-naphthol 
• 62-53-3 aniline 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 872277-07-1 1-hydroxy-[2]thionaphthoic acid anilide 
• 56-23-5 tetrachloromethane 
• 38357-69-6 2-methylphenyl phenylcarbamate 
• 7446-70-0 aluminium trichloride 
• 38077-69-9 1-hydroxy-2-naphthoyl chloride 
• 132-54-7 phenyl 1-hydroxy-2-naphthoate 

Downstream Products

• 50729-25-4 4-bromo-1-hydroxy-[2]naphthoic acid anilide 
• 36120-42-0 4-[Benzo[1,2]dithiol-(3E)-ylidene-hydrazono]-1-oxo-1,4-dihydro-naphthalene-2-carboxylic acid phenylamide 
• 13545-94-3 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3-methyl-benzothiazolium betaine 
• 104999-62-4 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3-phenyl-4,5,6,7-tetrahydro-benzothiazolium betaine 
• 62353-89-3 morpholine-4-carboxylic acid N-(1-hydroxy-naphthalene-2-carbonyl)-anilide 
• 68719-65-3 1-Hydroxy-4-(4-nitro-phenylsulfanyl)-naphthalene-2-carboxylic acid phenylamide 
• 100736-16-1 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3,4-dimethyl-thiazolium betaine 
• 100738-65-6 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3,4,5-trimethyl-thiazolium betaine 
• 103006-31-1 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-4-methyl-3-p-tolyl-thiazolium betaine 
• 101956-33-6 4-tert-butyl-2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3-methyl-thiazolium betaine 
• 5649-70-7 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3-phenyl-thiazolium betaine 
• 104400-22-8 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3-methyl-4,5,6,7-tetrahydro-benzothiazolium betaine 
• 41338-80-1 2-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-3,4-diphenyl-thiazolium betaine 
• 35976-32-0 3-(4-hydroxy-3-phenylcarbamoyl-naphthalen-1-ylazo)-2-methyl-benzo[d]isothiazolium betaine 

Relevant articles and documents

Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity

Twenty-two novel antimycobacterial agents, 1-hydroxynaphthalene-2-carboxanilides, were studied by cyclic voltammetry on a glassy carbon electrode in a phosphate buffer pH 7.2 – dimethyl sulfoxide (DMSO) mixed medium (9:1; v/v). All compounds exhibited similar voltammetric behavior with one irreversible anodic signal in the range 100–300 mV corresponding to the oxidation of hydroxyl group on the naphthalene moiety. A shift of the oxidation potential was caused solely by electron donating or withdrawing effects of substituents and their position on the benzene moiety. Mechanism of oxidation in the studied medium was briefly outlined. Values of oxidation potentials exhibited very good linear correlation with calculated Hammett σ substituent constants. For all active compounds, a relationship between oxidation potentials and MIC or IC50 values obtained from in vitro screening was investigated in detail. Primary in vitro screening of synthesized compounds was previously performed against three species of Mycobacterium pathogens. Additionally, their activity related to the inhibition of photosynthetic electron transport (PET) in spinach chloroplasts was tested in previous publications. In vitro screening against Mycobacterium tuberculosis was performed here for the first time with 1-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-2-carboxamide being the most effective (MIC = 11.7 μmol L?1). Furthermore, several other compounds showed higher antimycobacterial activity than the standard isoniazid. Relation of biological activities and oxidation potentials was successfully found in some cases; however, final correlations must also be considered with other physical and chemical factors contributing to the biological activity. Relation of structure, biological activity and electrochemical potential was also studied by cyclic voltammetry in cathodic area for three compounds containing reducible nitro moiety.

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.

N-alkoxyphenylhydroxynaphthalenecarboxamides and their antimycobacterial activity

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 synthes