Microwave assisted synthesis of novel pyrazolone derivatives attached to a pyrimidine moiety and evaluation of their anti-inflammatory, analgesic and antipyretic activities

Abstract

In the present research work, the motto was to develop new chemical entities as potential anti-inflammatory, analgesic and antipyretic agents. Various 4-(2-amino-6-(substituted)pyrimidin-4-yl)-3-methyl-1-(substituted)-1H-pyrazol-5(4H)-one derivatives (5a-5j) and their Schiff bases (6a-6j) were synthesized. The newly synthesized compounds were characterized by TLC and spectral data. The compounds containing pyrazolone and amino pyrimidine as basic moieties (5a-5j), were screened for their anti-inflammatory, analgesic and antipyretic activities, compounds 5a, 5c-5f, 5h exhibited activities nearly similar to the standard. The pharmacological studies reveal that the presence of 4-hydroxy, 4-methoxy, 4-(N,N-dimethylamino) or 2-hydroxy groups on phenyl ring at C6 of amino pyrimidine exhibits anti-inflammatory, analgesic and antipyretic activities nearly similar to the standard and substitutions like 4-chloro, 2-nitro, 3-nitro or 4-nitro on same phenyl ring lead to a decrease in activities.

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

“…A cluster of pyrazolone and amino pyrimidine derivatives 119e124 (Fig. 11) were synthesized by Antre and co-workers [92], with obvious anti-inflammatory potency in carrageenan-induced rat paw edema model (Table 10). In regard to SAR, in contrast to the substitution of chlorine and nitro, the anti-inflammatory effects of these analogues were significantly promoted when the electrondonating groups of C-6 aminopyrimidine benzene ring were hydroxyl, methoxy and dimethylamine.…”

Synthesis, Characterization of Poly Heterocyclic Compounds, and Effect on Cancer Cell (Hep-2) In vitro.

“…It is also an important pharmacophore of top selling harmaceutical drugs such as, Azelastine, Ameziniummetalilsulfate, Emorfazone, Cadralazine, Hydralazine, Minaprine and Sulfamethoxypyridazine. Pyridazine molecule and its derivatives are also known to possess a wide range of biological activities, such as anticancer, antiviral, antituberculosis, antidepressant, analgesic, antimicrobial and in platelet aggregation (21)(22)(23)(24)(25). The aim of the reasearch is the synthesis and characterization of organic compounds and study the effect of compounds on cancer cell line (Hep-2).…”

In vitro antioxidant and in vivo antidepressant activity of green synthesized azomethine derivatives of cinnamaldehyde

“…[ 11 ] Similarly, Schiff bases have been reported for antibacterial,[ 12 13 ] antifungal,[ 14 ] antiproliferative,[ 15 16 ] and antipyretic properties. [ 17 ] During the entire preceding history of medicine, fewer of drugs had known the focus of action, and then fewer had been submitted to synthetic investigations. It is an evident fact that azomethines with aryl substituents are more stable and readily synthesized, whereas those containing alkyl substituents are relatively unstable.…”