ISSN : 2663-2187

Pyrazoline Derivatives: Synthesis, Structural Characterization, and Pharmacological Assessment via TLC and NMR

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Kapil Kumar, Smriti Gohri, Divya Patak
» doi: 10.48047/AFJBS.6.14.2024.3316-3333

Abstract

A thorough thin-layer chromatography (TLC) examination was performed on pre-coated silica plates (604 GF 254 Merck) to determine the identity and evaluate the purity of different synthesized chemical compounds. The solvent system used included carbon tetrachloride and acetone in different proportions. The substances exhibited distinct chromatographic behaviors, as shown by the Rf values ranging from 0.54 to 0.72. The chromatograms were observed using a UV chamber, which confirmed the existence of separate spots for each synthesized derivative, so proving their purity. The synthesized chemicals were further characterized using Nuclear Magnetic Resonance (NMR) spectroscopy. The 1H NMR spectra of derivatives such as 4-(5-(4 nitrophenyl)-1H-pyrazol-3-yl) phenol, 4-(5-(4-chlorophenyl)-1H pyrazol-3-yl) phenol, 4-(5-(4-bromophenyl)-1H-pyrazol-3-yl) phenol, and 4-(5-(p-tolyl)-1H-pyrazol-3-yl) phenol were examined, yielding comprehensive insights into their molecular structures. The synthesis technique produced a range of compounds with varying substituents. The percentage yields for the derivatives of 3-(4-substituted phenyl)-1 (4-hydroxyphenyl) prop-2-en-1-one varied from 60.89% to 82.78%. Similarly, the production of derivatives of 4-(5-phenyl)-1H-pyrazol-3 yl) phenol resulted in yields ranging from 61.24% to 80.95%. The synthesized compounds were analysed to identify their physicochemical characteristics, including molecular weight, colour, and melting point. In addition, solubility experiments were conducted using several solvents, revealing that the compounds were mostly soluble in methanol, DMSO, and acetone, while being insoluble in water. The antibacterial and anti-inflammatory properties of the synthesized compounds were assessed. The anti-inflammatory action was evaluated using the membrane stabilisation method, in which the compounds demonstrated substantial inhibition of haemolysis, similar to the standard medication Diclofenac sodium. The compounds exhibited diverse effectiveness in preventing haemolysis, with values ranging from 19.53% to 64.32%. Finally, the compounds were evaluated for their anthel mintic activity against the earthworm species Eisenia foetida and Eisenia engeniae. The synthesized compounds exhibited significant action, causing paralysis and death in a similar timeframe as the conventional medicine Piperazine citrate.

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