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A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities

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Abstract

A series of new coumarin derivatives 4 containing a chalcone moiety were synthesized by condensation of 3-acetyl-4-hydroxycoumarin 1 with aryl or heteroaryl aldehydes 2 in the presence of piperidine in chloroform. The interaction of 3-formyl-4-chloro-coumarin 3 with nitrogen compound nucleophiles are described and lead to the corresponding substituted chromen[4,3-c] pyrazol-4-ones 5. The structures of the obtained compounds were established on the basis of IR|1D|2D NMR, while crystal structure of 3-acetyl-4-hydroxy coumarin 1 was determined using X-ray diffraction and further were evaluated for possible antibacterial and antioxidant activities. The coumarinic chalcone 4d has been found to be the most active (IC50 = 2.07 μM) in this study.

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Scheme 1
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Fig. 2
Scheme 2
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Scheme 4
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Abbreviations

LTR:

Long terminal repeat

TPA:

Two photon absorption

AIDS:

Acquired immunodeficiency syndrome

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Acknowledgements

This work was carried out with financial aid of both Tunisian Ministry of Higher Education and Scientific Research and Technology and the Spanish Agency of International Cooperation through projects (A/9549/07and A/8302/07).

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Authors and Affiliations

  1. Borj Cedria Higher Institute of Sciences and Technology, Environment Touristic Road of Soliman B.P. 95., 2050, Hammam-Lif, Tunisia

    Naceur Hamdi

  2. CNRS-UMR “Sciences Chimiques de Rennes”, Université Rennes 1, Laboratoire Catalyse et Organométalliques, 263 avenue du général Leclerc Bâtiment 10C, 35042, Rennes cedex, France

    Cédric Fischmeister

  3. Departamento de Ciencia de los Materiales Ingeniería Metalúrgica y Química Inorgánica, Facultad de Ciencias, Universidad de Cádiz, Campus del Río San Pedro, 11510, Puerto Real, Spain

    M. Carmen Puerta & Pedro Valerga

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  1. Naceur Hamdi
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  2. Cédric Fischmeister
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  3. M. Carmen Puerta
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  4. Pedro Valerga
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Correspondence to Naceur Hamdi.

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Hamdi, N., Fischmeister, C., Puerta, M.C. et al. A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities. Med Chem Res 20, 522–530 (2011). https://doi.org/10.1007/s00044-010-9326-1

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  • DOI: https://doi.org/10.1007/s00044-010-9326-1

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