An efficient and novel synthesis of chromonyl chalcones using recyclable Zn(l-proline)2 catalyst in water

Siddiqui, Zeba N.; Musthafa, T. N. Mohammed

doi:10.1016/j.tetlet.2011.05.118

Cited by 29 publications

(15 citation statements)

References 42 publications

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“…The presence of three electrondeficient carbons (C-2, C-4 and CHO) on the 3-formylchromone structure makes this compound an exceptional starting material for several nucleofilic additions, which in turn can lead to a great diversity of derivatives. Taking advantage of these features, several heterocyclic substituted chromones were obtained, namely with aza [294,295] , diaza [170,296] , oxa [297] and dithiazole [298][299][300][301][302] groups as well as vinyl chromone derivatives [303,304] (scheme 2.13).…”

Section: Synthesis Of Chromones From Other Chromonesmentioning

confidence: 99%

Chromone: A Valid Scaffold in Medicinal Chemistry

et al. 2014

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The last few decades have provided stunning progresses in the understanding of physiopathology of several diseases. The remarkable progress in research fields, like genetics, immunology, neurobiology, among others, as well as the advent of more powerful tools, have made it possible to characterize, monitor, and understand far more of the basis of physiology and disease. However, for some diseases the treatment remains a problematic issue as the efforts performed so far were not translated into therapeutic solutions. Notwithstanding the steady increase in the total amount of FCUP

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Section: Synthesis Of Chromones From Other Chromonesmentioning

confidence: 99%

Chromone: A Valid Scaffold in Medicinal Chemistry

et al. 2014

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“…On the other side, chalcones family correspond to flavanoid class and have shown a remarkable range of biological activities [103] . Bis[( l )prolinate-N,O]Zn catalyzed the preparation of a library of chromonyl chalcones ( 85 ) from different cyclic active methyl groups ( 84 ) and 3-formylchromones ( 83 ) [104] . The yield of substituted chromonyl chalcones was found to 79–92% in 15–30 mins ( Scheme 19 ).…”

Section: Bis[( L )Prolinate-no]zn In Organic Syntmentioning

confidence: 99%

Bis[( l )prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Poddar

Jain

Kidwai

2017

Journal of Advanced Research

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“…Производные (E)-3-(3-(4-оксо-4H-хромен-3-ил) акрилоил)-2H-хромен-2-она получают конденсацией 3-формилхромона с 3-ацетилкумарином в спирте с использованием в качестве катализатора органиче-ских оснований -N,N-диметиламинопиридина [21] или пиперидина [22]. Для этой реакции в различных условиях изучены каталитические свойства кислот Льюиса [23,24]. Однако, на наш взгляд, данный синтетический подход не может быть применен при введении во взаимодействие 3-формилхромона ввиду высокой реакционной способности положения С(2): в присутствии даже слабых нуклеофилов происходит раскрытие пиронового цикла с формированием замещенных фенолов.…”

Section: результаты и обсуждениеunclassified

Synthesis and Antioxidant Activity of (E)-3-(3-(4-Oxo-4h-Chromen-3-Yl)acryloyl) 2h-Chromen-2-One Derivatives

Shatokhin

Тuskaev

Гагиева

et al. 2021

Farm. farmakol. (Pâtigorsk)

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The aim is based on the results of the in silico prediction, to obtain and characterize a number of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one derivatives, and also to study their antioxidant activity.Materials and methods. The synthesis of the target compounds was carried out by condensation of substituted 3-formylchromones and 3-acetylcoumarins under the acid catalysis conditions. 1H NMR spectra were recorded on the instruments of Bruker Avance-400 (400 MHz) and Bruker Avance-300 (300 MHz) in the solutions of CDCl3 or DMSO-d6. Mass spectra (ESI) were obtained on a Finnigan LCQ Advantage mass spectrometer (USA). The melting points of the compounds were determined on a PTP (M) instrument. Quantum-chemical calculations were carried out on the basis of a density functional theory using the Gaussian 09 program using the B3LYP/6-311G (d, p) method, as well as using the Way2Drug (PASS Online) online service. The antiradical activity of the compounds was studied by the DPPH test, and the chelating properties were assessed by the o-phenanthroline method.Results. 15 derivatives of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one have been obtained and characterized. The calculations based on the density functional theory showed that the highest occupied molecular orbital exhibiting electron-donating properties is localized on the propenone fragment, which confirms the likelihood of the manifestation of antiradical properties. According to the prediction of the probable spectrum of the biological activity, the obtained compounds are more likely to exhibit their direct antioxidant activity. According to the results of the in vitro study of the antioxidant activity, it was found out that compounds 1-15 are the most active in relation to the DPPH radical, which confirms the obtained prognostic data.Conclusion. Thus, based on the in silico prediction data, 15 derivatives of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one have been obtained and characterized, for which the method antioxidant activity has been studied in vitro. It was found out that compounds 1-15 exhibit the antiradical activity to a large extent.

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An efficient and novel synthesis of chromonyl chalcones using recyclable Zn(l-proline)2 catalyst in water

Cited by 29 publications

References 42 publications

Chromone: A Valid Scaffold in Medicinal Chemistry

Chromone: A Valid Scaffold in Medicinal Chemistry

Bis[( l )prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Synthesis and Antioxidant Activity of (E)-3-(3-(4-Oxo-4h-Chromen-3-Yl)acryloyl) 2h-Chromen-2-One Derivatives

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