Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions

Ramana, P. Venkata; Reddy, A. Ramachandra

doi:10.5155/eurjchem.2.3.300-307.358

Cited by 3 publications

(2 citation statements)

References 18 publications

(9 reference statements)

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“…Cyclization with ethyl acetoacetate was furnished isoxazole ester C, which upon saponification with sodium hydroxide yielded compound 8 . Carboxylic acid 8 was further coupled with methyl glycinate hydrochloride under amide coupling conditions using HATU to give compound 9 .…”

Section: Resultsmentioning

confidence: 99%

New Anti‐Inflammatory Hybrid N‐Acyl Hydrazone‐Linked Isoxazole Derivatives as COX‐2 Inhibitors:Rational Design, Synthesis and Biological Evaluation

et al. 2017

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Selectivity of a drug becomes a major problem in the treatment of a clinical disease and many nonsteroidal anti‐inflammatory drugs (NSAID's) are classic examples of this conundrum. In the present study, we designed a set of hybrid compounds (11 a‐p, 12 a‐i) that compose new N‐acyl hydrazones (NAH) linked with isoxazoles, using rational drug design approach. The binding affinities of newly designed compounds were calculated and compared with known non anti‐inflammatory NAH and cyclooxygenase‐2 (COX‐2) inhibitors (coxibs) at the active sites of cyclooxygenase‐1 (COX‐1) and COX‐2. The comparison revealed that the hybrid compounds bind with COX‐2 active site in a fashion quite similar to known non anti‐inflammatory compounds (4). Based on these findings, we further synthesized the compounds (11 a‐p, 12 a‐i) and subjected them to in vitro, in vivo anti‐inflammatory studies. Compound 11 l (IC50=5.8 μM) and 12 c (IC50 = 4.1 μM) were found to be active COX‐2 inhibitors. Compounds 12 a, 12 b and 12 e displayed COX‐2 enzyme inhibition at lower micro molar concentrations. The compounds were also evaluated for antioxidant activity and compound 11 h exhibited an effective antioxidant activity when compared with ascorbic acid. Additionally, these compounds were screened for anti‐bacterial activities and compound 11 l and 12 h were exhibited greater anti‐bacterial activity against gram +ve and ‐ve than standards Ciprofloxacin and Flucloxacillin.

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Section: Resultsmentioning

confidence: 99%

New Anti‐Inflammatory Hybrid N‐Acyl Hydrazone‐Linked Isoxazole Derivatives as COX‐2 Inhibitors:Rational Design, Synthesis and Biological Evaluation

et al. 2017

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“…The therapeutic importance of this nucleus has enthused us to develop selective molecules in which substituent could be arranged in a pharmacophoric pattern to display high‐order pharmacological activity. In last few years, the use of microwave irradiation in organic reactions as well as in the synthesis of pharmaceutical compounds is rapidly increasing due to short duration of time of reaction and high yield with purity . This newer technology is emerging as an alternative energy source capable enough to complete chemical reactions within few seconds or minutes.…”

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confidence: 99%

Discovery of HIV‐1 Integrase Inhibitors: Pharmacophore Mapping, Virtual Screening, Molecular Docking, Synthesis, and Biological Evaluation

2013

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HIV-1 integrase enzyme plays an important role in the life cycle of HIV and responsible for integration of virus into human genome. Here, both computational and synthetic approaches were used to design and synthesize newer HIV-1 integrase inhibitors. Pharmacophore mapping was performed on 20 chemically diverse molecules using DISCOtech, and refinement was carried out using GASP. Ten pharmacophore models were generated, and model 2, containing four features including two donor sites, one acceptor atom, and one hydrophobic region, was considered the best model as it has the highest fitness score. It was used as a query in NCI and Maybridge databases. Molecules having more than 99% Q(fit) value were used to design 30 molecules bearing pteridine ring and were docked on co-crystal structure of HIV-1 integrase enzyme. Among these, six molecules, showing good docking score compared with the reference standards, were synthesized by conventional as well as microwave-assisted methods. All compounds were characterized by physical and spectral data and evaluated for in vitro anti-HIV activity against the replication of HIV-1 (IIIB) in MT-4 cells. The used approach of molecular docking and anti-HIV activity data of designed molecules will provide significant insights to discover novel HIV-1 Integrase Inhibitors.

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Amino- and fluoro-substituted quinoline-4-carboxylic acid derivatives: MWI synthesis, cytotoxic activity, apoptotic DNA fragmentation and molecular docking studies

Bhatt

Agrawal

Patel³

2014

Med Chem Res

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Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions

Cited by 3 publications

References 18 publications

New Anti‐Inflammatory Hybrid N‐Acyl Hydrazone‐Linked Isoxazole Derivatives as COX‐2 Inhibitors:Rational Design, Synthesis and Biological Evaluation

New Anti‐Inflammatory Hybrid N‐Acyl Hydrazone‐Linked Isoxazole Derivatives as COX‐2 Inhibitors:Rational Design, Synthesis and Biological Evaluation

Discovery of HIV‐1 Integrase Inhibitors: Pharmacophore Mapping, Virtual Screening, Molecular Docking, Synthesis, and Biological Evaluation

Amino- and fluoro-substituted quinoline-4-carboxylic acid derivatives: MWI synthesis, cytotoxic activity, apoptotic DNA fragmentation and molecular docking studies

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