Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

Evtushok, Vasilii E.; Vorob’ev, Aleksey Yu.

doi:10.1007/s10593-019-02446-0

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…Evtushak and Vorob’ev described the synthesis of 9-hydroxypyrazolo[1,5-a] quinolones and 2-substituted-9-hydroxy[1,2,4] triazolo[1,5-a]quinolones, as shown in Scheme 24 [ 65 ]. Concerning the former derivatives, the N -amination of 1 was achieved by using O -(mesitylenesulfonyl)hydroxylamine (MSH) as an N -aminating agent [ 66 ] to produce 1-amino-8-hydroxyquinolonium mesitylenesulfonate ( 101 ).…”

Section: New Chemistrymentioning

confidence: 99%

Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines

2020

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Compounds containing the 8-hydroxyquinoline (8-HQ) 1 nucleus exhibit a wide range of biological activities, including antimicrobial, anticancer, and antifungal effects. The chemistry and biology of this group have attracted the attention of chemists, medicinal chemists, and professionals in health sciences. A number of prescribed drugs incorporate this group, and numerous 8-HQ- based molecules can be used to develop potent lead compounds with good efficacy and low toxicity. This review focusses on the recent advances in the synthesis of 8-HQ derivatives with different pharmacological properties, including anticancer, antiviral, and antibacterial activities. For this purpose, recent relevant references were searched in different known databases and search engines, such as MEDLINE (PubMed), Google Scholar, Science Direct, Scopus, Cochrane, Scientific Information Database (SID), SciFinder, and Institute for Scientific Information (ISI) Web of Knowledge. This review article provides a literature overview of the various synthetic strategies and biological activities of 8-HQ derivatives and covers the recent related literature. Taken together, compounds containing the 8-HQ moiety have huge therapeutic value and can act as potential building blocks for various pharmacologically active scaffolds. In addition, several described compounds in this review could act leads for the development of drugs against numerous diseases including cancer.

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Section: New Chemistrymentioning

confidence: 99%

Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines

2020

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“…Because the reaction is exothermic, the water might cause the carboxyl hydrolysis to become acid under alkaline conditions. Several synthesis methods of the pyrazole aromatic ketone have been reported, one from pyrazolone and acyl chloride, then rearrangement under base‐catalysis. Another method is from methamiprid and pyrazole, then hydrosis to afford the pyrazole‐4‐one.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor

Cai

et al. 2019

Pest Management Science

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BACKGROUND 4‐Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been a good target for herbicide discovery. In order to discover novel HPPD herbicides, a series of pyrazole aromatic ketone analogs were designed and synthesized. RESULTS The 25 pyrazole aromatic ketone analogs synthesized were tested for herbicidal activity and compounds A1, A3, A4, A17, A20 and A25 displayed excellent herbicidal activity against Chenopodium serotinum, Stellaria media and Brassica juncea at 37.5 g ha−1. In addition, compounds A1, A5, A9, A10, A16, A17, A20 and A25 exhibited good crop selectivity for wheat, maize and rice at 150 g ha−1. Inhibition activities against AtHPPD proved the compounds were HPPD inhibitors. The structure–activity relationship of these pyrazole aromatic ketone analogs was studied using molecular docking. CONCLUSION These pyrazole aromatic ketone derivatives could be used as lead structures for development of HPPD herbicides against dicotyledonous weeds with further structure modification. © 2019 Society of Chemical Industry

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Dimethyl Sulfoxide-Assisted, Iodine- and Ascorbic Acid-Catalyzed One-Pot Synthetic Approach for Constructing Highly Substituted Pyrazolo[1,5-a]quinoline Thioether Derivatives

et al. 2022

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A dimethyl sulfoxide-assisted and iodine/ascorbic acidcatalyzed simple approach to pyrazolo[1,5-a]quinoline thioether derivatives 22 is described. The compounds were identified using 1 H NMR, 13 C NMR, high-resolution mass spectrometry, and single-crystal X-ray diffractometry. The pyrazolo[1,5-a]quinoline thioether was synthesized in a stepwise fashion through aryl sulfenylation and benzannulation strategies. The generated heteroaryl thioether compounds 23 were exposed to the benzannulation path to produce pyrazolo[1,5-a]quinoline thioether 22. The benzannulation reaction proceeds by way of diazotization of the pyrazole amine derivative 23, radical generation by the removal of nitrogen, and eventually trapping of the aryl radical with the support of phenylacetylene 19. A catalytic amount of ascorbic acid aided the benzannulation reaction. There were several other control studies conducted, including trapping reactions with isopropenyl acetate, tetramethylpiperidine N-oxyl reactions, and reactions without phenylacetylene. Since a change in the substitution has previously demonstrated substantial bioactivity, the core structure of pyrazole was evaluated for functional group tolerance. A reasonable mechanism is then proposed, accompanied by the support of control experiments and scope. A Suzuki reaction was used to create an aryl/heteroaryl compound 35 from one of the synthesized compounds 22b. In the controlled oxidation reaction paths, molecule 22a was selectively transformed into the corresponding sulfoxide 32 and sulfone 33.

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Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

Cited by 6 publications

References 22 publications

Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines

Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines

Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor

Dimethyl Sulfoxide-Assisted, Iodine- and Ascorbic Acid-Catalyzed One-Pot Synthetic Approach for Constructing Highly Substituted Pyrazolo[1,5-a]quinoline Thioether Derivatives

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