Design, Synthesis, Characterization and Biological Evaluation of Some Novel 1, 5 Disubstituted Tetrazole as Potential Anti-Inflammatory Agents (original) (raw)
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Acta Poloniae Pharmaceutica - Drug Research
A series of heterocyclic derivatives including 1,2,4-triazole-3(4H)-one (3a,b), 1H-pyrazol-5(4H)-one (4,5), 1H-pyrazol-4-carbonitrile (7), pyridine-3-carbonitrile (8, 9a,b), pyrimidine-5-carbonitrile (10a,b), methylpyrimidin-2(1H)-one or thione (11a,b), pyrimidine-5-carboxylate (12a,b), quinazolin-5(6H)-one (13a,b) and indeno [1,2-d] pyrimidin-5-one (14a,b) moieties conjugated with 1,3-disubstituted pyrazole moiety were synthesized on reaction with semicarbazide, thiosemicarbazide, 3-amino-5-oxo-2-pyrazoline, cyanoacetohydrazide, 2-acetyl thiophene, p-chloroacetophenone, urea, thiourea and 1,3-dicarbonyl compounds, respectively, by using 1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole-4-carboxaldehyde (2) as starting material. The structures of all the newly synthesized products have been established on the basis of analytical and spectral data. The anti-inflammatory screening showed that most of the obtained compounds were found to have significant anti-inflammatory activities w...
Asian Journal of Chemistry; Vol. 32, No. 3 (2020), 607-611, 2020
Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for their anti-inflammatory potentiality. The structures of the synthesized compounds were elucidated using FTIR, NMR (1H & 13C) and mass spectral data. The study found that the activity of aminomethyl derivatives (2a-e) was higher than that of parent compound 1. In this series, aminomethyl derivatives bearing dimethylamino-methyl, diethylaminomethyl and pyrrolidinomethyl moieties (2a, 2c and 2e, respectively) were more active than diclofenac sodium, which was used as a standard. A study on the structure-activity relationship (SAR) suggested that the activity of aminomethyl moiety of the compound was influenced by its pKa value. Thus, novel compounds act as potential anti-inflammatory agents. Keywords: 1,5-Diarylpyrazole, Aminomethyl derivatives, Anti-inflammatory activity, Protein denaturation.
Abstract Anovel series of 2-pyrazoline derivatives 13a–l was synthesized via aldol condensation of 4-substituted acetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-hydrazinobenzenesulfonamide hydrochloride. The chemical structures of the target pyrazoline derivatives were proved by means of IR, 1HNMR, 13C NMR, mass spectroscopy and elemental analyses data. All the synthesized compounds were evaluated for their cyclooxygenase selectivity, anti-inflammatory and ulcerogenic liability. While compounds 13e, 13h and 13i showed moderate COX-2 selectivity in vitro and good anti-inflammatory activity in vivo, compound 13i showed the highest anti-inflammatory activity that is very close in potency to the reference drug (celecoxib) with better gastric profile than celecoxib.
Pyrazole is a 5-membered heterocyclic ring three carbon atoms and two adjacent nitrogen centres. Pyrazole is the organic compound with the formula C3H3N2H. Pyrazoles are also the class of compounds that have the ring C3N2 with adjacent nitrogen centre. Pyrazoles are synthesized by the reaction of α, β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation. In the present study, we synthesized different Pyrazoles derivatives (5a, 5b, 5c) (6a, 6b, 6c, 6e) (7a, 7b, 7d) by treating substituted acetophenones with Phenyl hydrazine a by using glacial acetic acid and ethanol as solvent. The respective substituted acetophenone phenylhydrazone were then treated with Vilsmeier Hack Reagent which gives respective carbaldehydes. Then carbaldehydes were treated with 3 different amine compounds that give new Pyrazole derivatives. The prepared Pyrazole derivatives were recrystallized with ethanol. The final compounds were then characterized by melting point, TLC, IR and NMR spectral data. These compounds were evaluated for anti-inflammatory activity. Some of the newly synthesized compounds showed the significant activity when compared with the standard compounds
Indian Journal of Chemical Technology
The present study is the synthesis of new heterocyclic moieties like pyrazole, isoxazole and thiazole containing benzimidazole nucleus. The title compounds were synthesized from 4-(1H-benzo[d]imidazol-2-yl) oxazol-2-amine. The newly synthesised compounds were screened for their in vitro anti-inflammatory activity and demonstrated excellent to moderate activity and molecular docking study reports are supporting anti-inflammatory activity showed high inhibition constant and binding energy. The structures of synthesised compounds were characterized by IR, 1 HNMR, Mass spectroscopic methods.
TNF-α and IL-1β inhibitors, 3, 5-disubstituted-4, 5-dihydro-1H-pyrazoles
Biomedical Research-tokyo, 2017
A series of 3, 5-disubstituted-4, 5-dihydro-1H-pyrazoles have been synthesized under solvent free microwave irradiation method by the condensation of α, β-unsaturated ketones with hydrazine and its differently substituted derivatives. The chemical structures of the compounds were characterized by elemental analysis and spectroscopic data. All the synthetics were evaluated for their anti-inflammatory activity under in vivo conditions. The present study describes the potential of these pyrazole ring containing scaffolds to assess the TNF α (Tumor Necrosis Factor-alpha) and IL-1β (Interleukin-1 beta) inhibitory potential. TNF-α and IL-1β are inflammatory cytokines that are pro-inflammatory in nature and play a major role in inflammatory cascades of many pathologically dreadful diseases ranging from neurodegenerative disorders to autoimmune diseases such as rheumatoid arthritis.
2017
Some novel 4-(5-methylisoxazol-3-ylamino) thiazole derivatives incorporated with different heterocyclic moieties were synthesized and screened for their anti-inflammatory activity. Compounds (1, 2, 10, 11, 12, 13) screened for their anti-inflammatory activity. Among them, compound 13 showed the greatest anti-inflammatory potency. Furthermore, compound 2 showed the least anti-inflammatory potency. Molecular modeling simulation was done to explore the binding mode of these compounds within active sites of trypsin and bovine serum albumin.
Synthesis, characterization, analgesic and anti-inflammatory activity of new pyrazole derivatives
Arkivoc, 2020
The synthesis of nine new pyrazole derivatives was achieved from β-hydroxy enones and hydrazines by using a trace of piperidine in methanol at room temperature. The use of piperidine provides more yield and purity of products in lesser time when compared to the other reagents. All synthetic compounds were characterized by their physical properties, NMR and LC mass spectral data. The pyrazole derivatives were screened for their analgesic and anti-inflammatory activities in vivo. The derivatives exhibited moderate to significant activities in comparison to control, and most of the pyrazoles were competent with standard drugs (Pentazocine and Indomethacin).