European Journal of Chemistry

Synthesis, reactions, antioxidant and anticancer evaluation of some novel coumarin derivatives using ethyl 2-(2-oxo-4-phenyl-2H-chromen-7-yloxy) acetate as a starting material

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Published: Mar 31, 2014
DOI: https://doi.org/10.5155/eurjchem.5.1.111-121.860
Keywords:
Triazole, Oxadiazole, Cytotoxicity, Benzoimidazole, Antioxidant activity, Coumarinacetohydrazide
Section
Research Article
Issue
Vol. 5 No. 1 (2014): March 2014
Dates
Received 2013-06-15
Accepted 2013-09-15
Published 2014-03-31


Main Article Content

Ahmed Hamdy Halawa
Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
Ahmed Abd El-Hameed Hassan
Chemistry Department, Faculty of Medicine, Jazan Universit y, 82621, Jazan, Saudi Arabia
Mohamed Ahmed El-Nassag
Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
Mahmoud Mohamed Abd El-All
Chemistry Department, Faculty of Science and Art, Al-Baha University, 1988, Al-Baha, Saudi Arabia
GehadAbd El-Raheem Abd El-Jaleel
Pharmacology Department, National Research Center, 12622, Dokki, Cairo, Egypt
Essam Mohamed Eliwa
Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
Ahmed Hammam Bedair
Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt

Abstract

We report on the synthesis of new coumarin derivatives coupled with heterocyclic and bifunctionalized moieties at position 7. The proposed structures were confirmed by correct elemental analysis and spectral data (IR, MS, 1H NMR and 13C NMR). Some selected derivatives were also screened for their antioxidant and anticancer activities. The results indicated that 7-{[6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl]methoxy}-4-phenyl-H-chromen-2-one has the highest antioxidant and anticancer activity in tested compounds.


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Halawa, A. H.; Hassan, A. A. E.-H.; El-Nassag, M. A.; Abd El-All, M. M.; Abd El-Jaleel, G. E.-R.; Eliwa, E. M.; Bedair, A. H. Synthesis, Reactions, Antioxidant and Anticancer Evaluation of Some Novel Coumarin Derivatives Using Ethyl 2-(2-Oxo-4-Phenyl-2H-Chromen-7-Yloxy) Acetate As a Starting Material. Eur. J. Chem. 2014, 5, 111-121.

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References

[1]. Chakraborty, D. P.; Chatterji, D. J. Org. Chem. 1969, 34(12), 3784-3786.
http://dx.doi.org/10.1021/jo01264a009

[2]. Finnegan, R. A.; Morris, M. P.; Djerassi, C. J. Org. Chem. 1961, 26(4), 1180-1184.
http://dx.doi.org/10.1021/jo01063a050

[3]. Al-Amiery, A. A.; Ahmed, Y. M.; Abdul Amir, H. K.; Abu Bakar, M. Molecules 2011, 16, 6833-6843.
http://dx.doi.org/10.3390/molecules16086833

[4]. Holho, D.; Boschetti, E.; Lipha, Fr. Pat. No. 1, 310, 535; 1963.

[5]. Meguro, K.; Tawada, H.; Jpn. Pat. No. 90129, 240; 1991.

[6]. Anderson, D. M.; Shelley, S.; Crick, N.; Buraglio, M. J. Clin. Pharmacol. 2002, 42, 1358-1365.
http://dx.doi.org/10.1177/0091270002238772

[7]. Tassies, D.; Freire, C.; Puoan, J.; Maragall, S.; Monteagudo, J. Haematologica 2002, 87, 1185-1191.

[8]. Vittorio, F.; Ronsisvalle, G.; Marrazzo, A.; Blandini, G. Farmaco 1995, 50, 265-272.

[9]. Nayyar, V.; Monga, A.; Malde, E.; Coutinho, R. Bioorg. Med. Chem. 2007, 15, 626-640.
http://dx.doi.org/10.1016/j.bmc.2006.10.064

[10]. Sztanke, K.; Pasterhak, K.; Rzymowska, J.; Sztanke, M.; Kandefer-Szerszen, M. Eur. J. Med. Chem. 2007, 43, 404-419.
http://dx.doi.org/10.1016/j.ejmech.2007.03.033

[11]. Radhwan, M. A. A.; Ragab, E. A.; Sabry, N. M.; El-Shenawy, S. M. Bioorg. Med. Chem. 2007, 15, 3832-3841.
http://dx.doi.org/10.1016/j.bmc.2007.03.024

[12]. Gemma, S.; Kukreja, G.; Fattorusso, C.; Persico, M.; Romano, M. P.; Altarelli, M.; Savini, L.; Campiani, G.; Fattorusso, E.; Basilico, N.; Taramelli, D.; Yardley, V.; Butini, S. Bioorg. Med. Chem. Lett. 2006, 16, 5384-5388.
http://dx.doi.org/10.1016/j.bmcl.2006.07.060

[13]. Al-Mawsawi, L. Q.; Dayam, R.; Taheri, L.; Witvrouw, M.; Debyser, Z.; Neamati, N. Bioorg. Med. Chem. Lett. 2007, 17, 6472-6475.
http://dx.doi.org/10.1016/j.bmcl.2007.09.102

[14]. Hansch, C.; Fujita, T. J. Am. Chem. Soc. 1964, 86, 1616-1626.
http://dx.doi.org/10.1021/ja01062a035

[15]. Kamal, M. D.; Ahmad, M. F.; Hatem, A. A. Heteroatom. Chem. 2005, 16, 621-627.
http://dx.doi.org/10.1002/hc.20162

[16]. Abdel-Al, E. H.; Al-Ashamawi, M. I.; Abd El-Fattah, B. Arch. Pharm. 1983, 38, 833-838.

[17]. Gupta, A.K.S.; Garg, M.; Chandra, U. J. Indian Chem. Soc. 1979, 56, 1230-1232.

[18]. Mansour, A. K.; Eid, M. M.; Khalil, N. S. A. M. Molecules 2003, 8, 744-755.
http://dx.doi.org/10.3390/81000744

[19]. Walser, A.; Flynn, T.; Mason, C. J. Heterocycl. Chem. 1991, 28, 1121-1125.
http://dx.doi.org/10.1002/jhet.5570280448

[20]. Reiter, J.; Pongo, L.; Kovesdi, I.; Pallagi, I. J. Heterocycl. Chem. 1995, 32, 407-417.
http://dx.doi.org/10.1002/jhet.5570320206

[21]. Anderson, D. K.; Deuwer, D. L.; Sirkorski, J. A. J. Heterocycl. Chem. 1995, 32, 893-898.
http://dx.doi.org/10.1002/jhet.5570320336

[22]. Collin, X.; Sauleau, A.; Coulon, J. Bioorg. Med. Chem. Lett. 2003, 13, 2601-2605.
http://dx.doi.org/10.1016/S0960-894X(03)00378-0

[23]. Goswami, B. N.; Kataky, J. C. S.; Baruah, J. N. J. Indian Chem. Soc. 1987, 64, 422-424.

[24]. Hirota, T.; Sasaki, K.; Yamamoto, H.; Nakayama, T. J. Heterocycl. Chem. 1991, 28, 257-261.
http://dx.doi.org/10.1002/jhet.5570280209

[25]. Al-Soud, Y. A.; Al-Masoudi, N. A.; Ferwanah, A. E. S. Bioorg. Med. Chem. 2003, 11, 1701-1708.
http://dx.doi.org/10.1016/S0968-0896(03)00043-9

[26]. Garazd, M. M.; Garazd, Ya. L.; Smirnov, M. N.; Khilya, V. P. Chem. Nat. Compd. 1999, 35, 415-419.
http://dx.doi.org/10.1007/BF02282506

[27]. Schlesier, K.; Harwat, M.; Böhm, V.; Bitsch, R. Free Radic. Res. 2002, 36, 177-187.
http://dx.doi.org/10.1080/10715760290006411

[28]. Kadhum, A. H.; Al-Amiery, A. A.; Musa, A. Y.; Mohamad, A. B. Int. J. Mol. Sci.2011, 12, 5747-5761.
http://dx.doi.org/10.3390/ijms12095747

[29]. Sumangala, V.; Boja, P.; Chidananda, N.; Arulmoli, T.; Shalini, S. Eur. J. Med. Chem. 2012, 54, 59-64.
http://dx.doi.org/10.1016/j.ejmech.2012.04.024

[30]. El-Agrody, A. M.; Ali, F. M.; Eid, F. A.; El-Nassag, M. A.; El-Sherbeny, A. G.; Bedair, A. H. Phosphorous Sulfur 2006, 18, 839-864.
http://dx.doi.org/10.1080/10426500500272087

[31]. Abd El-Wahab, A. H. F.; Mohamed, H. M.; El-Agrody, A. M.; El-Nassag, M. A.; Bedair, A. H. Eur. J. Chem. 2013, 4, 10-19.
http://dx.doi.org/10.5155/eurjchem.4.1.10-19.707

[32]. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Lebensm. Wiss. Technol. 1995, 28, 25-30.
http://dx.doi.org/10.1016/S0023-6438(95)80008-5

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Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
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