92-73-9

Usage

Uses

Used in Textile Industry:
N-(2,5-Dimethoxyphenyl)-3-hydroxy-2-naphthamide is used as a dyeing agent for cotton, viscose, and silk. It is not typically used for printing due to its medium affinity for cotton. This product is suitable for dyeing various textiles, providing color and enhancing the appearance of fabrics.

Preparation

2,5-Dimethoxyaniline and 3-Hydroxy-2-naphthoic acid condensation.

Upstream product

• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 102-56-7 2,5-dimethoxyaniline 
• 39110-32-2 3-hydroxynaphthalene-2-carboxylic acid 

Relevant academic research and scientific papers

Photosynthesis-inhibiting activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides

A set of twenty-four 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by combinations of methoxy/methyl/fluoro/chloro/bromo and ditrifluoromethyl groups at different positions, was prepared. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3,5-Difluorophenyl)-, N-(3,5-dimethylphenyl)-, N-(2,5-difluorophenyl)-and N-(2,5-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamides showed the highest PET-inhibiting activity (IC50 ~ 10 μM) within the series. These compounds were able to inhibit PET in photosystem II. It has been found that PET-inhibiting activity strongly depends on the position of the individual substituents on the anilide ring and on the lipophilicity of the compounds. The electron-withdrawing properties of the substituents contribute towards the PET activity of these compounds.

Consensus-based pharmacophore mapping for new set of n-(Disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides

A series of twenty-two novel N-(disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamide derivatives was synthesized and characterized as potential antimicrobial agents. N-[3,5-bis(trifluoromethyl)phenyl]-and N-[2-chloro-5-(trifluoromethyl)phenyl]-3-hydroxy-naphthalene-2-carboxamide showed submicromolar (MICs 0.16–0.68 μM) activity against methicillin-resistant Staphylococcus aureus isolates. N-[3,5-bis(trifluoromethyl)phenyl]-and N-[4-bromo-3-(trifluoromethyl)phenyl]-3-hydroxynaphthalene-2-carboxamide revealed activity against M. tuberculosis (both MICs 10 μM) comparable with that of rifampicin. Synergistic activity was observed for the combinations of ciprofloxacin with N-[4-bromo-3-(trifluoromethyl)phenyl]-and N-(4-bromo-3-fluorophenyl)-3-hydroxynaphthalene-2-carboxamides against MRSA SA 630 isolate. The similarity-related property space assessment for the congeneric series of structurally related carboxamide derivatives was performed using the principal component analysis. Interestingly, different distribution of mono-halogenated carboxamide derivatives with the –CF3 substituent is accompanied by the increased activity profile. A symmetric matrix of Tanimoto coefficients indicated the structural dissimilarities of dichloro-and dimetoxy-substituted isomers from the remaining ones. Moreover, the quantitative sampling of similarity-related activity landscape provided a subtle picture of favorable and disallowed structural modifications that are valid for determining activity cliffs. Finally, the advanced method of neural network quantitative SAR was engaged to illustrate the key 3D steric/electronic/lipophilic features of the ligand-site composition by the systematic probing of the functional group.