Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles

Lobo, Prajwal L.; Poojary, Boja; Kumsi, Manjunatha; chandra, Vinaya; Kumari, Nalilu Sucheta; Chandrashekar, K. R.

doi:10.1007/s00044-012-0154-3

Cited by 17 publications

(11 citation statements)

References 22 publications

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“…The di-halogenated compounds exhibited significant DPPH RSA than the corresponding chloro-substituted compounds. Pyrazole derivative 3e and 6e show the most potent antioxidant activity, both having 3,4 (di-Cl) substituents on phenyl ring, which is in accordance with the reported results 67 . Presence of electron donating groups such as OCH 3 and CH 3 are more beneficial than unsubstituted or mono chloro-substituted phenyl ring, which may be due to þ I and mesomeric effects 68 .…”

Section: Dpph Scavenging Activitysupporting

confidence: 91%

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Ali

Awad

Said

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxidative stress is one of the main causes of significant severe diseases. The discovery of new potent antioxidants with high efficiency and low toxicity is a great demand in the field of medicinal chemistry. Herein, we report the design, synthesis molecular modelling and biological evaluation of novel hybrids containing pyrazole, naphthalene and pyrazoline/isoxazoline moiety. Chalcones 2a-e were synthesized efficiently and were used as starting materials for synthesis of a variety of heterocycles. A novel series of pyrazoline 3a-e, phenylpyrazoline 4a-e, isoxazoline 5a-e and pyrazoline carbothioamide derivatives 6a-e were synthesized and screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO) and superoxide radical scavenging assay as well as 15-lipoxygenase (15-LOX) inhibition activity. Compounds 3a, 4e, 5b, 5c, 6a, 6c, and 6e showed excellent radical scavenging activity in all three methods in comparison with ascorbic acid and 15-LOX inhibition potency using quercetin as standard then were subjected to in vivo study. Catalase (CAT) activity, glutathione (GSH) and malondialdehyde (MDA) levels were assayed in liver of treated rats. Compounds 5b, 5c, and 6e showed significant in vivo antioxidant potentials compared to control group at dose of 100 mg/kg B.W. Molecular docking of compound 6a endorsed its proper binding at the active site pocket of the human 15-LOX which explains its potent antioxidant activity in comparison with standard ascorbic acid.

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Section: Dpph Scavenging Activitysupporting

confidence: 91%

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Ali

Awad

Said

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…A series of 2 H -pyrazolyl-1-carbothioamides showed good inhibitory activity against the proliferation of HepG-2 cells, Hela cells and A549 cancer cells. Structure-activity relationship (SAR) studies revealed that the activity of pyrazoline and its derivatives is dependent on the presence of the nitrogen heterocyclic moiety [ 14 ], which is a structural subunit that is known to have a variety of pharmacological properties and widespread medical biological activities [ 15 ]. On the other hand, most 2 H -pyrazole derivatives are chiral molecules, providing a greater degree of variability in conformation and substitutions, leading to better biological activity [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

A New Series of Cytotoxic Pyrazoline Derivatives as Potential Anticancer Agents that Induce Cell Cycle Arrest and Apoptosis

Wang

Zheng

et al. 2017

Molecules

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A new series of pyrazoline derivatives 1b–12b was designed, synthesized and evaluated for antiproliferative activity against three cancer cell lines (HepG-2, Hela and A549). Additionally, NIH/3T3 cell cytotoxicity were tested and the structure activity relationships (SARs) were also determined. Among these new derivatives, the compounds 3-(4-fluorophenyl)-5-(3,4,5-trimethoxythiophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (1b) and 3-(4-chlorophenyl)-5-(3,4,5-trimethoxythiphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (2b) showed the best activity against HepG-2 cells, with IC50 values of 6.78 μM and 16.02 μM, respectively. They also displayed potent activity against Hela cells; meanwhile, 3-(4-chlorophenyl)-5-(3-bromo-4-hydroxy-5-methoxythiophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (5b) and 3-(4-bromo-phenyl)-5-(3-bromo-4-hydroxy-5-methoxythiophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (6b) were also identified as promising anticancer agents against A549 cells owing to their notable inhibitory effect, compared with cisplatin (IC50 = 29.48 μM). Furthermore, it was also found that compounds 1b and 2b had low cytotoxicity against NIH/3T3 cells and further mechanistic studies revealed that 1b arrested HepG-2 cells cycle at the G2/M phase at high concentrations and induced apoptosis in HepG-2 cells. Moreover, 1b upregulated protein expression level of cleaved caspase-3, cleaved PARP, Bax and p53 and downregulated protein expression level of Bcl-2 in dose-dependent way in HepG-2 cells. Thus, this study indicates that compound 1b might be a promising antitumor drug candidate.

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“…Also, 6i and 6l with good antibacterial activity possess the furyl moiety. Recently it was shown that the presence of Cl substituent has a positive effect on the antibacterial activity, and in this study the Cl‐substituted product 6h showed high antibacterial activity …”

Section: Resultsmentioning

confidence: 52%

Sequential one‐pot multicomponent synthesis of bis‐aminothiazols and evaluation of their antibacterial and antioxidant activities

Parvizi

Mahmoodi

Pirbasti

2018

J Chinese Chemical Soc

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A series of novel bis-thiazoles were synthesized through a one-pot semi-fivecomponent reaction of the prepared α-bisbromo ketones, aldehydes, and thiosemicarbazide in the presence of p-TsOH under reflux condition. Products were obtained in reasonable yields via an efficient, convenient, and simple setup. The inhibitory activity on bacterial growth of the products was studied against Gramnegative (Escherichia coli and Pseudomonas aeruginosa) and Gram-positive bacterial strains (Micrococcus luteus, Staphylococcus aureus) at different concentrations (25, 50, 100, and 200 μg/mL at 600 nm). Most of the products showed inhibitory activity at the concentration of 200 μg/mL. In addition, bis-thiazoles showeed high to moderate antioxidant activity using the diphenylpicrylhydrazyl (DPPH) method. Bis-thiazoles 6i and 6j showed higher antioxidant activity than vitamin C and vitamin E.

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Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles

Cited by 17 publications

References 22 publications

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

A New Series of Cytotoxic Pyrazoline Derivatives as Potential Anticancer Agents that Induce Cell Cycle Arrest and Apoptosis

Sequential one‐pot multicomponent synthesis of bis‐aminothiazols and evaluation of their antibacterial and antioxidant activities

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