Synthesis of Pyrazole and Isoxazole in Triethanolamine Medium.

Agrawal, Nitin N.; Soni, P. A.

doi:10.1002/chin.200729039

Cited by 6 publications

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“…Chalcones dibromides, obtained from the treatment of chalcones with bromine, afforded pyrazoles by the reaction with benzoylhydrazines [186] and phenylhydrazines [115] in dry pyridine or hydrazines in triethanolamine [187], and 2-pyrazolines by the reaction with phenylhydrazine or isonicotinic acid hydrazide in DMF (Scheme 20) [188]. A series of bispyrazoles can be accomplished through the reaction of bischalcones tetrabromo derivatives with hydrazine hydrate in refluxing methanol [189].…”

Section: Transformation Of Chalcones To Pyrazolesmentioning

confidence: 99%

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Albuquerque¹,

Santos²,

Cavaleiro³

et al. 2014

COC

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Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The ,-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5-and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21 st century in more than 400 publications.

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Section: Transformation Of Chalcones To Pyrazolesmentioning

confidence: 99%

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Albuquerque¹,

Santos²,

Cavaleiro³

et al. 2014

COC

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“…The chalcones are precursors in the biosynthetic pathways of flavonoids, isoflavonoids, and aurone, which reportedly have wide-ranging pharmacological activities, such as antifungal (Zhao et al, 2007), antibacterial (Nielsen et al, 2005), antioxidant (Aichaoui et al, 2009), anticancer (Mahmoodi et al, 2014), antiprotozoal (Kiat et al, 2006), antiinflammatory (Seo et al, 2005), antimalarial (Awasthi et al, 2009), anti-HIV (Cheenpracha et al, 2006), anti-angiogenic (Varinska et al, 2012), cyclooxygenase inhibitory (Sharma, 2014) and tyrosine phosphatase 1B inhibitory activities (Sun et al, 2012). Chalcones and their α,β-dibromo derivatives (2,3-dibromo-1,3-diphenyl-2-propen-1-one) are used as intermediates for the syntheses of various heterocyclic compounds, such as flavones, flavonols, aziridines, coumarones, quinolines, pyrazoles and isooxazoles (Tökés et al, 1992;Wróblewski et al, 2000;Agrawal & Soni, 2007). A survey of the literature revealed that α,β-dibromochalcones and their derivatives also possess a wide range of biological activities, which include antioxidant (Lahsasni et al, 2014), antimicrobial (Rahman et al, 2012), anti-angiogenic (Robinson et al, 2005), quinine reductase-inducing (Dinkova-Kostova et al, 1998), cytotoxic (Modzelewska et al, 2006) and cholesterol-lowering activities (Piantadosi et al, 1973).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents

2015

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In the present study, a series of chalcone derivatives including 17 new compounds were synthesised; their antibacterial activities against eleven bacteria, and their free radical-scavenging activities using DPPH were evaluated. All compounds showed significant antibacterial activities against both Grampositive and Gram-negative bacteria. In particular, compound IIIf strongly inhibited Staphylococcus aureus (JMC 2151) and Enterococcus faecalis (CARS 2011-012) with MIC values of 6.25 µg mL −1 and 12.5 µg mL −1 , respectively, which are comparable to that of the standard antibiotic, nalidixic acid. Compound IIIg also inhibited S. aureus with a MIC value similar to that of nalidixic acid (6.25 µg mL −1 ). Furthermore, like nalidixic acid (MIC value of 25 µg mL −1 ), compounds IIIa, IIIc and IIId inhibited Listeria monocytogenes (ATCC 43256) with MIC values of 25 µg mL −1 , 12.5 µg mL −1 and 25 µg mL −1 , respectively. Quantitative structure-activity relationship (Q-SAR) studies using physicochemical calculations indicated that the antibacterial activities of chalcone derivatives correlated well with predicted physicochemical parameters (logP and PSA). Docking simulation by positioning the most active compound IIIf in the active site of the penicillin-binding protein (PBP-1b) of S. aureus was performed to explore the feasible binding mode. Furthermore, most of the compounds synthesised exhibited significant DPPH radical-scavenging activity, although compounds IIc and IIIc exhibited the greatest antioxidant activity with IC50 values of 1.68 µM and 1.44 µM, respectively, comparable to that of the standard antioxidant, ascorbic acid (1.03 µM).

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Exploration of chalcones and related heterocycle compounds as ligands of adenosine receptors: therapeutics development

et al. 2021

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Synthesis of Pyrazole and Isoxazole in Triethanolamine Medium.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 6 publications

References 0 publications

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents

Exploration of chalcones and related heterocycle compounds as ligands of adenosine receptors: therapeutics development

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