European Journal of Chemistry 2014, 5(3), 457-462 | doi: https://doi.org/10.5155/eurjchem.5.3.457-462.1040 | Get rights and content

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Synthesis of new 3,4-dihydropyrano[c]chromene derivatives and their evaluation as acetyl cholinesterase inhibitors


Younes Bouazizi (1) , Anis Romdhane (2,*) , Hichem Ben Jannet (3)

(1) Chemistry Department, Faculty of Science, Jazan University, 2097, Saudi Arabia
(2) Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Bioorganic Chemistry and Natural Products, Faculty of Sciences, University of Monastir, Monastir, 5000, Tunisia
(3) Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Bioorganic Chemistry and Natural Products, Faculty of Sciences, University of Monastir, Monastir, 5000, Tunisia
(*) Corresponding Author

Received: 02 Mar 2014 | Accepted: 27 Apr 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


2-Amino-4-phenyl-4,5-dihydro-5-oxopyrano[2,3-c]chromen-3-carbonitrile derivatives (8a-d) have been isolated in good yields by the reaction of corresponding 4-hydroxycoumarin (1) with substituted aldehydes (2a-d) and malononitrile (3) under reflux conditions. The reactivity of α-functionalized iminoethers (9a-d) with hydrazine, hydroxylamine and piperidine was studied. The synthesized compounds were characterized by various techniques including spectroscopy. Compounds 8-11 were also evaluated as potential acetylcholinesterase inhibitors.


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Editor-in-Chief
European Journal of Chemistry

Keywords


Chromene; Iminoethers; Pyrrolochromene; Pyridinochromene; Dihydropyrano[c]chromene; Anti-acetylcholinesterase activity

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DOI: 10.5155/eurjchem.5.3.457-462.1040

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Citations

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[1]. Leila Dinparast, Hassan Valizadeh, Esmail Vessally, Mir Babak Bahadori
Synthesis, characterization and DFT studies of diethyl 4-hydroxy-6-nitro-4H-chromene-2,3-dicarboxylate
Journal of Molecular Structure  1105, 118, 2016
DOI: 10.1016/j.molstruc.2015.10.044
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[2]. Maher Cherif, Mabrouk Horchani, Youssef O. Al-Ghamdi, Sami G. Almalki, Yaser E. Alqurashi, Hichem Ben Jannet, Anis Romdhane
New pyrano-1,2,3-triazolopyrimidinone derivatives as anticholinesterase and antibacterial agents: Design, microwave-assisted synthesis and molecular docking study
Journal of Molecular Structure  1220, 128685, 2020
DOI: 10.1016/j.molstruc.2020.128685
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[3]. Soraya Rahmatinejad, Hossein Naeimi
Design, preparation, and characterization of Fe3O4 nanoparticles encapsulating β‐cyclodextrin‐bearing guanidine as a highly efficient and reusable heterogeneous base catalyst for synthesis of 3,4‐dihydropyrano[3,2‐c]chromenes
Applied Organometallic Chemistry  34(10), , 2020
DOI: 10.1002/aoc.5862
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[4]. Najet Aouled Dlala, Younes Bouazizi, Houcine Ghalla, Naceur Hamdi, Pasquale Longo
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DOI: 10.1155/2021/6674261
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[5]. Pooja Garg, Sabbasani Rajasekhara Reddy
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[6]. Arezou Mohammadinezhad, Batool Akhlaghinia
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DOI: 10.1071/CH17093
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[7]. Amel Hajlaoui, Maha Laajimi, Mansour Znati, Hichem Ben Jannet, Anis Romdhane
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References


[1]. Adami, E.; Marazzi-Uberti, E.; Turba, C. Arch. Ital. Sci. Farmacol. 1959, 9, 61-69.

[2]. Arvind, B. T.; Venkat, S. S.; Narayan, D. S.; Devanand, B. S. Bull. Environ. Pharmacol. Life Sci. 2012, 7, 30-33.

[3]. Luchini, A. C.; Rodrigues-Orsi, P.; Cestari, S. H.; Seito, L. N.; Witaicenis, A.; Pellizzon, C. H. Biol. Pharm. Bull. 2008, 31, 1343-1350.
http://dx.doi.org/10.1248/bpb.31.1343

[4]. Jae-Chul, J; Qee-Sook, P. Molecules 2009, 14, 4790-4803.
http://dx.doi.org/10.3390/molecules14114790

[5]. Chohan, Z. H.; Shaikh, A. U.; Rauf, A.; Supuran, C. T. J. Enz. Inhib. Med. Chem. 2006, 21, 741-748.
http://dx.doi.org/10.1080/14756360600810340

[6]. Kirkiacharian, B. S.; Clercq, E.; Kurkjian, R.; Pannecouque, C. J. Pharm. Chem. 2008, 42, 265-270.
http://dx.doi.org/10.1007/s11094-008-0103-0

[7]. Velasco-Velazquez, M. A.; Agramonte-Hevia, J.; Barrera, D.; Jimenez-Orozco, A.; Garcia-Mondragon, M. J.; Mendoza-Patino, N.; Landa, A.; Mandoki, J. Cancer. Lett. 2003, 198, 179-186.

[8]. Shapiro, S.; Sherwin, B. N. Y. State J. Med. 1943, 43, 45-52.

[9]. Butsch, W. L.; Stewart, J. D. Arch. Surg. 1942, 45, 551-553.
http://dx.doi.org/10.1001/archsurg.1942.01220040047005

[10]. Hintz, K. K.; Ren, J. Vascul. Pharmacol. 2003, 40, 213-217.
http://dx.doi.org/10.1016/j.vph.2003.08.002

[11]. Manolov, I.; Maichle-Moessmer, C.; Danchev, N. Eur. J. Med. Chem. 2006, 41, 882-890.
http://dx.doi.org/10.1016/j.ejmech.2006.03.007

[12]. Howes, M. R.; Houghton, P. J. Pharmacol. Biochem. Behav. 2003, 75, 513-527.
http://dx.doi.org/10.1016/S0091-3057(03)00128-X

[13]. Saudi, M. N. S.; Gaafar, M. R.; El-Azzouni, M. Z.; Ibrahim, M. A.; Eissa, M. M. Chem. Res. 2008, 17, 541-563.

[14]. Sunduru, N.; Agawal, A.; Katiyar, S.; Nishi, B.; Goyal, N.; Gupta, S.; Chauhan, P. M. S. Bioorg. Med. Chem. 2006, 14, 7706-7715.
http://dx.doi.org/10.1016/j.bmc.2006.08.009

[15]. Huisgen, R. J. Org. Chem 1976, 41, 403-419.
http://dx.doi.org/10.1021/jo00865a001

[16]. Pinner, A.; Klein, F. Ber. Dtsch. Chem. Ges 1877, 10, 1889-1897
http://dx.doi.org/10.1002/cber.187701002154

[17]. Orhan, G.; Orhan, I.; Sener, B. Lett. Drug. Desig. Discov. 2006, 3, 268-274.
http://dx.doi.org/10.2174/157018006776743215


How to cite


Bouazizi, Y.; Romdhane, A.; Jannet, H. Eur. J. Chem. 2014, 5(3), 457-462. doi:10.5155/eurjchem.5.3.457-462.1040
Bouazizi, Y.; Romdhane, A.; Jannet, H. Synthesis of new 3,4-dihydropyrano[c]chromene derivatives and their evaluation as acetyl cholinesterase inhibitors. Eur. J. Chem. 2014, 5(3), 457-462. doi:10.5155/eurjchem.5.3.457-462.1040
Bouazizi, Y., Romdhane, A., & Jannet, H. (2014). Synthesis of new 3,4-dihydropyrano[c]chromene derivatives and their evaluation as acetyl cholinesterase inhibitors. European Journal of Chemistry, 5(3), 457-462. doi:10.5155/eurjchem.5.3.457-462.1040
Bouazizi, Younes, Anis Romdhane, & Hichem Ben Jannet. "Synthesis of new 3,4-dihydropyrano[c]chromene derivatives and their evaluation as acetyl cholinesterase inhibitors." European Journal of Chemistry [Online], 5.3 (2014): 457-462. Web. 10 Dec. 2023
Bouazizi, Younes, Romdhane, Anis, AND Jannet, Hichem. "Synthesis of new 3,4-dihydropyrano[c]chromene derivatives and their evaluation as acetyl cholinesterase inhibitors" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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