Novel crystal forms of 4-aminoantipyrine and its derivatives: Co-crystallizing a reluctant molecule

Smith, Mark; Lemmerer, Andreas

doi:10.1016/j.molstruc.2018.07.062

Cited by 11 publications

(3 citation statements)

References 21 publications

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“…23,25,26 To date, several literature reviews focusing on antipyrine (API) co-crystals with suitable co-formers namely salicylic acid, 27 saccharin, fumaric acid, 28 4-aminobenzoic acid, 29 sulphanilamide, 30 4,4′-propane-2,2′-diyldiantipyrine 31 and sulfaguanidine 32,33 have been published. In addition, the literature also contains cocrystals of phenazone derivatives like propyphenazone–pyrithyldione, 34 propyphenazone–hydroquinone, 35 4-aminoantipyrine-fumaric acid, 28 4-aminoantipyrine-2-amino benzoic acid, 36 etc. ; but no high-resolution study is available focusing on the electron density derived properties and the nature of intermolecular forces.…”

Section: Introductionmentioning

confidence: 99%

Crystal engineering of a co-crystal of antipyrine and 2-chlorobenzoic acid: relative energetic contributions based on multipolar refinement

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Crystal engineering of a co-crystal of antipyrine and 2-chlorobenzoic acid: relative energetic contributions based on multipolar refinement

et al. 2022

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“…In order to reduce the associated side effects with the non-steroidal anti-inflammatory (NSAID) drugs, specifically 4-aminophenazone, efforts have been directed in developing the cocrystals of this unique pharmacophore with ultimate enhanced effect on its biophysical properties. So far, to the best of our knowledge, only eleven molecular salts of 4-aminoantipyrine (4-AAP) have yet been reported [30][31][32][33][34][35], two of which are simple salts with halide counter-ions. Some representative examples of 4-aminophenazone salts are highlighted in Figure 2 [35].…”

Section: Introductionmentioning

confidence: 99%

“…So far, to the best of our knowledge, only eleven molecular salts of 4-aminoantipyrine (4-AAP) have yet been reported [30][31][32][33][34][35], two of which are simple salts with halide counter-ions. Some representative examples of 4-aminophenazone salts are highlighted in Figure 2 [35]. The pyrazolone nucleus is important in pharmaceutical industry and a variety of synthetic drugs contain this core entity [24].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Hirshfeld Surface Investigations for Unexpected Aminophenazone Cocrystal Formation under Thiourea Reaction Conditions via Possible Enamine Assisted Rearrangement

et al. 2022

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Considering the astounding biomedicine properties of pharmaceutically active drug, 4-aminophenazone, also known as 4-aminoantipyrine, the work reported in this manuscript details the formation of novel cocrystals of rearranged 4-aminophenazone and 4-nitro-N-(4-nitrobenzoyl) benzamide in 1:1 stoichiometry under employed conditions for thiourea synthesis by exploiting the use of its active amino component. However, detailed analysis via various characterization techniques such as FT-IR, nuclear magnetic resonance spectroscopy and single crystal XRD, for this unforeseen, but useful cocrystalline synthetic adduct (4 and 5) prompted us to delve into its mechanistic pathway under provided reaction conditions. The coformer 4-nitro-N-(4-nitrobenzoyl) benzamide originates via nucleophilic addition reaction following tetrahedral mechanism between para-nitro substituted benzoyl amide and its acid halide (1). While the enamine nucleophilic addition reaction by 4-aminophenazone on 4-nitrosubstituted aroyl isothiocyanates under reflux temperature suggests the emergence of rearranged counterpart of cocrystal named N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonothioyl)-4-nitrobenzamide. Crystallographic studies reveal triclinic system P-1 space group for cocrystal (4 and 5) and depicts two different crystallographically independent molecules with prominent C–H···O and N–H···O hydrogen bonding effective for structure stabilization. Hirshfeld surface analysis also displays hydrogen bonding and van der Waals interactions as dominant interactions in crystal packing. Further insight into the cocrystal synthetic methodologies supported the occurrence of solution-based evaporation/cocrystallization methodology in our case during purification step, promoting the synthesis of this first-ever reported novel cocrystal of 4-aminophenazone with promising future application in medicinal industry.

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The scavenging mechanism of aminopyrines towards hydroxyl radical: A computational mechanistic and kinetics investigation

Kaur

Mandal

2023

Computational and Theoretical Chemistry

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Novel crystal forms of 4-aminoantipyrine and its derivatives: Co-crystallizing a reluctant molecule

Cited by 11 publications

References 21 publications

Crystal engineering of a co-crystal of antipyrine and 2-chlorobenzoic acid: relative energetic contributions based on multipolar refinement

Crystal engineering of a co-crystal of antipyrine and 2-chlorobenzoic acid: relative energetic contributions based on multipolar refinement

Experimental and Hirshfeld Surface Investigations for Unexpected Aminophenazone Cocrystal Formation under Thiourea Reaction Conditions via Possible Enamine Assisted Rearrangement

The scavenging mechanism of aminopyrines towards hydroxyl radical: A computational mechanistic and kinetics investigation

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