Synthesis of Novel 1,2-Diol Containing Azo Dyes for Polymeric Substrates

Sheikh, Hamdullah Khadim; Kazmi, Mehdi Hassan

doi:10.4067/s0717-97072017000200014

Cited by 3 publications

(2 citation statements)

References 12 publications

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“…Compound (3), ( 7) and (8) were synthesized using methods described in the literature (Sheikh and Kazmi, 2017) (Scheme 1). For synthesis of (11a-11d) and ( 14), carbonyldiimidazole (CDI) (4) (8 mmol) and fatty acid (9a-9d) (8 mmol) were dissolved in tetrahydrofuran (THF) solvent.…”

Section: Synthesismentioning

confidence: 99%

Untitled

2023

Pak. J. Pharm. Sci.,

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Lipid A is a fragment of lipopolysaccharide (LPS) in gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa; hence inhibition of its biosynthesis is one of the plausible ways of preventing such bacteria from growth and thus preventing gastrointestinal diseases caused by Escherichia coli and pseudomonas aeruginosa. This research revolves around the development of antibiotic glyceride derivatives for the inhibition of the biosynthesis of lipid A. To target the enzymes involved in the biosynthesis of lipid A, four N,N-dimethylaminobenzoate moiety containing fatty diglyceride derivatives were synthesized through a multi-step synthetic scheme starting from glycerol. The molecular structure of the targeted molecules and synthesized intermediates in the synthetic scheme were confirmed by detailed structural analysis through 1 N-NMR, mass and IR spectroscopic techniques. Antibacterial activity was evaluated against the gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). The derivatives also underwent docking analysis on the pdb's of enzymatic catalysts involved in the biosynthesis of lipid A using AutoDock Vina package. All synthesized fatty esters gave good antibacterial activity and binding energy upto -7 kcal/mol in the docking analysis. A structure-property relationship was established between alkyl chain lengths of diglycerides and their resultant binding energies. These molecules and their resultant activity can assist in further designing and retrosynthesis of molecular derivatives of drug molecules with lipid A biosynthesis as target for its inhibition.

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Section: Synthesismentioning

confidence: 99%

Untitled

2023

Pak. J. Pharm. Sci.,

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“…Azo dyes are widely used in the textile industry and are the largest and most versatile group of synthetic organic dyes, with a tremendous number of industrial applications [ 13 ]. Azo dyes are characterized by the presence of one or more azo group (-N=N-) in association with two or more aromatic or heterocyclic system, in which many heterocyclic compounds are used extensively in disperse dye preparation for textile or nontextile applications [ 5 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Comparative study and dyeing performance of as-synthesized azo heterocyclic monomeric, polymeric, and commercial disperse dyes

Abdullahi¹,

MUSA²,

HABIBU³

et al. 2022

Turkish Journal of Chemistry

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In this study poly (4-nitrophenylazo-3-aminopyridine - formaldehyde) (PNAAP-F) and poly (4-nitroarylazo-3-chloro-6-hydroxypyridine - formaldehyde) (NAACHP-F) were synthesized via diazotization, coupling and polycondensation reactions. The structural properties of the as-synthesized dyes were acquired using Fourier-transform infrared spectroscopy (FTIR) and UV-visible absorption maxima and their color, yield, melting point, solubility, and viscosity were determined via standard methods. UV-visible and FTIR results show successful formation of the polymeric dyes due to shift of wavelength of maximum absorption ( λ max ) (440–490 nm, 480–540 nm) and new absorption peak at around (2780–2995 cm −1 ) for methylene bridge respectively. The dyes were found to be of good yield (monomeric: 73.3%–87.2 %, polymeric: 53.8%–76.6 %), low melting point (monomeric: 112.6–121.2, and 136.0–137.0 °C, while polymeric: 134.0–144.5, and 149.4–154.7 °C), soluble in some solvents. The dyeing activity was carried out and assessed on nylon and polyester fabrics using the standard methods. The dyeing process was carried out via high temperature and carrier dyeing methods. The dyeing properties of the synthesized dyes were compared with those of commercial disperse dyes (terasil brilliant violet and terasil scarlet, brown). The dyeings of nylon and polyester had a very attractive hue and the color ranges from yellow and deep yellow shades with very good to excellent fastness to light, washing, hot pressing, and rubbing.

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