Green approach for drug design and discovery of paracetamol analogues as potential analgesic and antipyretic agents

Reddy, Y. D.; Reddy, Ch. Venkata Ramana; Dubey, P. K.

doi:10.1080/17518253.2014.895426

Cited by 9 publications

(5 citation statements)

References 9 publications

(7 reference statements)

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“…The catalytic efficiencies of the Au, Pt, and Pd NPs supported on the polymer/ND particles were probed using the reduction of p -nitrophenol (PNP) to p -aminophenol (PAP) with NaBH 4 , which is easily followed using UV–vis absorbance measurements . In addition to the convenient monitoring, this reaction is important because PAP is widely used as a precursor in the industrial synthesis of paracetamol (acetaminophen) . Nitrophenols have also been identified as priority pollutants, making their conversion to less toxic aminophenols a desirable environmental goal. , Without a catalyst, an aqueous mixture of PNP and NaBH 4 persists indefinitely as a clear, bright yellow solution with an absorbance at 400 nm.…”

Section: Results and Discussionmentioning

confidence: 99%

Robust Polymer-Coated Diamond Supports for Noble-Metal Nanoparticle Catalysts

et al. 2016

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Much research has been done using polymer and silica particles as support materials for catalytically active noble metal nanoparticles, but these materials have limited stability in organic solvents or under extreme reaction conditions such as high pH. Here we present a robust and versatile composite polymer-diamond support for ultrasmall noble metal nanoparticles combining chemical and mechanical stability of diamond with the chemical versatility of a polymer. By exploiting the rich surface chemistry of nanodiamond and incorporating a reactive thiol−ene polymer, a thinly coated polymer-diamond composite was formed. Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) confirmed the presence of the polymer. High resolution scanning transmission electron microscopy (S/TEM) analysis showed that in situ growth of gold, platinum and palladium nanoparticles produced high density coverage at the polymer-diamond support surface. Energy dispersive spectroscopy mapping and S/TEM imaging indicated spatial alignment of nanoparticles with chemical groups present in the polymer used for particle tethering. The polymer-diamond supported nanoparticles catalyze the NaBH 4 reduction of paranitrophenol to para-aminophenol and possess better stability than silica supports which dissolve at high pH resulting in nanoparticle aggregation. With the high robustness of the diamond and the ability to tailor the monomer combinations, this polymer-diamond support system may be expanded to a wide range of nanoparticle compositions suitable for various reaction conditions.

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Section: Results and Discussionmentioning

confidence: 99%

Robust Polymer-Coated Diamond Supports for Noble-Metal Nanoparticle Catalysts

et al. 2016

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“…Phthalimide-APAP derivatives 41–42 , structurally related to 37–38 , were prepared and proposed as potential analgesic and antipyretic agents but were not studied. 100,101…”

Section: Apap-prodrugs and -Hybrid Moleculesmentioning

confidence: 99%

“…Phthalimide-APAP derivatives 41-42, structurally related to 37-38, were prepared and proposed as potential analgesic and antipyretic agents but were not studied. 100,101 To avoid or moderate APAP-induced hepatotoxicity, the acetamide, -NH(CO)CH 3 fragment of APAP, was bioisosterically replaced with a 1,2,3-triazole scaffold constructing pharmacologically potent APAP-triazole derivatives such as 43-44 (Fig. 11).…”

Section: Carrier-linked O/n-modied Apap Prodrugsmentioning

confidence: 99%

Exploring acetaminophen prodrugs and hybrids: a review

Kouznetsov

2024

RSC Adv.

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“…Paracetamol crystals grown in water exhibit an elongated hexagonal morphology, with a prominent {1–10} facet growing along the crystallographic c -axis and {001}, {20–1}, and {0–11} as the smallest faces. This compound grown in other solvents such as polar protic, aprotic, and nonpolar solvents exhibits tetrahexahedron-like morphology with {00–1} as the dominant face. , It is very uncommon for polar protic solvents, which are more sustainable than the solvents commonly used by industrial manufacturers to produce crystals, to be used by industries . Solvents such as acetone, 4-chloroacetanilide, and 2-propanol are among the common solvents used by manufacturers but are less environmentally friendly …”

Section: Introductionmentioning

confidence: 99%

The Role of Solvent Hydroxyl Functional Groups on the Interaction Energy and Growth of Form I Paracetamol Crystal Facets

Shahrir

Anuar

Muttalib

et al. 2022

Org. Process Res. Dev.

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The morphology of a crystal grown in a solvent can change depending on the solvent used during the crystallization process. Modification of the morphology of a crystal can be engineered based on information conferred by the functional groups of the facets of interest and the functional groups of the solvent. This study aims to predict the effect of the alcoholic functional group of amyl alcohol, benzyl alcohol, and phenol on the {002}, {011}, and {110} facets of Form I paracetamol. Prediction and simulation studies were carried out using an embedded tool available in Material Studio. The interaction between the solvents (phenol, benzyl alcohol, and amyl alcohol) and the surfaces used in this study revealed that the {011} facet had the most negative nonbonded energy, followed by the {110} and {002} facets. Overall, the nonbonded interactions between the solvents and the facets were dominated by Coulombic interactions, accounting for more than 90% of the energies, which is within the range from −2566 to −3613 kcal/mol. The binding energy for amyl and benzyl alcohols on the facets of the crystal, ranked from the strongest to the weakest, was in the order {002} > {110} > {011}, while for phenol, the rank was {002} > {011} > {110}. This result is in line with the observed crystal morphology of Form I paracetamol crystallized in a polar protic solvent, in which the most favorable solvent binding on the {002} facets delayed the growth of the elongated hexagonal morphology along the c-axis and formed prismatic-like morphology. Using benzyl alcohol as a case study, an assessment of synthon formation on facets {002} and {011} showed that synthon B is an important synthon for the growth of units of these facets, while synthon F is an important building block synthon for the {110} facet.

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Green approach for drug design and discovery of paracetamol analogues as potential analgesic and antipyretic agents

Cited by 9 publications

References 9 publications

Robust Polymer-Coated Diamond Supports for Noble-Metal Nanoparticle Catalysts

Robust Polymer-Coated Diamond Supports for Noble-Metal Nanoparticle Catalysts

Exploring acetaminophen prodrugs and hybrids: a review

The Role of Solvent Hydroxyl Functional Groups on the Interaction Energy and Growth of Form I Paracetamol Crystal Facets

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