European Journal of Chemistry

Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives

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Published: Jun 30, 2012
DOI: https://doi.org/10.5155/eurjchem.3.2.220-227.592
Keywords:
Thiation, 2-Styrylchromones, 2-Methylchromone, Diels-Alder reaction, Biological evaluation, Heterocyclic transformations
Section
Research Article
Issue
Vol. 3 No. 2 (2012): June 2012
Dates
Received 2012-02-04
Accepted 2012-03-22
Published 2012-06-30


Main Article Content

Marwa Sayed Salem
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
Magda Ismail Marzouk
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
Salma Nasser Ali
Chemistry Department, Faculty of Science, 7Th October University, Bani Walid, 2478, Libya
Hassan Mohamed Fawzy Madkour
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt

Abstract

The typical active methyl functionality of 6,8-dichloro-2-methyl-4H-chromen-4-one is utilized to obtain 2-styrylchromones, pyruvate ester and phthalide via reactions with aromatic carboxaldehydes, diethyl oxalate and phthalic anhydride respectively. The phthalide provides illustrative example to convert a heterocyclic compound to an aliphatic one via the effect of alcoholic sodium methoxide. Bromination and cycloaddition reactions of 2-styrylchromones afford vicinal dibromide and adducts respectively. This work presents to the art a typical example of heterocyclic systems transformations through the conversion of the starting chromone to coumarin under the influence of thionyl chloride followed by aqueous potassium hydroxide. Some heterocyclic systems like pyrazole, isoxazol and quinolinone are obtained from the target chromone by treatment with hydrazines, hydroxylamine hydrochloride and ammonium acetate respectively. Thiation of starting chromone interestingly affords a dithiated product instead of the expected monothiated one. Antibacterial and antifungal activities of some synthesized compounds have been screened.

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Salem, M. S.; Marzouk, M. I.; Ali, S. N.; Madkour, H. M. F. Synthesis, Structure Characterization and Biological Evaluation of New 6,8-Dichloro-2-Methyl-4H-Chromen-4-One Derivatives. Eur. J. Chem. 2012, 3, 220-227.

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References

[1]. Huang, W.; Ding, Y.; Miao, Y.; Liu, M. Z.; Li Y.; Yang, G. F. Eur. J. Med. Chem. 2009, 44, 3687-3696.
http://dx.doi.org/10.1016/j.ejmech.2009.04.004
PMid:19410339

[2]. Lee, K. Y.; Nam, D. H.; Moon, C. S.; Seo, S. H.; Lee, J. Y.; Lee, Y. S. Eur. J. Med. Chem. 2006, 41, 991-996.
http://dx.doi.org/10.1016/j.ejmech.2006.04.008
PMid:16762460

[3]. McClure, J. W.; Harborne, J. B.; Mabry, T. J.; Mabry, H. The Flavonoids, Eds.; Chapman and Hall: London, 1975, pp. 970-1055.

[4]. Gamal, E. A. M.; Djemgou, P. C.; Tchuendem, M.; Ngadjui, B. T.; Tane, P.; Toshifumi, H. Z. Naturforsch. 2007, 62c, 331-338.

[5]. Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Biorg. Med. Chem. 2000, 8, 239-246.
http://dx.doi.org/10.1016/S0968-0896(99)00282-5

[6]. Lim, L. -C.; Kuo, Y. -C.; Chou, C. -J. J. Nat. Prod. 2000, 63, 627-630.
http://dx.doi.org/10.1021/np990538m
PMid:10843573

[7]. Shi, Y. Q.; Fukai, T.; Sakagami, H.; Chang, W. -J.; Yang, P. -Q.; Wang, F. -P.; Nomura, T. J. Nat. Prod. 2001, 64, 181-188.
http://dx.doi.org/10.1021/np000317c
PMid:11429996

[8]. Atassi, G.; Briet, P.; Berthelon, J. P.; Collonges, F. J. Med. Chem. 1985, 20, 393-402.

[9]. Pietta, P. J. J. Nat. Prod. 2000, 63, 1035-1042.
http://dx.doi.org/10.1021/np9904509
PMid:10924197

[10]. Middleton, Jr. E.; Kandaswami, C.; Arborne, J. B. The Flavonoids Advances in Research since 1986 Eds.; Chapman and Hall: London, 1994, pp. 619.

[11]. Bruneton, J. Pharmacognosy, Phytochemistry and Medicinal Plants; English Translation by Hatton, C. K.; Lavoisier Publishing: Paris. 1995; pp. 265.

[12]. Albrecht, U.; Lalk, M.; Langer, P. Bioorg. Med. Chem. 2005, 13, 1531-1536.
http://dx.doi.org/10.1016/j.bmc.2004.12.031

[13]. Deng, Y.; Lee, J. P.; Ramamonjy, M. T.; Synder, J. K.; Des Etages, S. A.; Kanada, D.; Synder, M. P.; Turner, C. J. J. Nat. Prod. 2000, 63, 1082-1089.
http://dx.doi.org/10.1021/np000054m
PMid:10978202

[14]. Khan, I. A.; Avery, M. A.; Burandt, C. L.; Goins, D. K.; Mikell, J. R.; Nash, T. E.; Azadega, A.; Walker, L. A. J. Nat. Prod. 2000, 63, 1414.
http://dx.doi.org/10.1021/np000010d
PMid:11076565

[15]. Mori, K.; Audran, G.; Monti, H. Synlett. 1998, 259-260.
http://dx.doi.org/10.1055/s-1998-1628

[16]. Harborne, J. B.; Williams, C. A. Phytochemistry 2000, 55, 481-504.
http://dx.doi.org/10.1016/S0031-9422(00)00235-1

[17]. Djemgou, P. C.; Gatsing, D.; Kenmogne, M.; Ngamga, D.; Aliyu, R.; Adebayo, A. H.; Tane, P.; Ngadjui, B. T.; Seguin, E.; Adoga, G. I. Res. J. Med. Plant 2007, 1(2), 65-71.
http://dx.doi.org/10.3923/rjmp.2007.65.71

[18]. Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H. Bioorg. Med. Chem. Lett. 2008, 18, 4678-4681.
http://dx.doi.org/10.1016/j.bmcl.2008.07.007

[19]. Groweiss, A.; Cardellins, J. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 1537.
http://dx.doi.org/10.1021/np000175m
PMid:11087602

[20]. Beecher, G. R. J. Nutr. 2003, 133, 3248-3254.

[21]. Hoult, J. R. S.; Moroney, M. A.; Paya, M. Methods Enzymol 1994, 234, 443-455.
http://dx.doi.org/10.1016/0076-6879(94)34115-X

[22]. Salem, M. A. I.; Hamed, A. A.; El-Shekeil, A. G.; Babaqui, A. S.; Madkour, H. M. F. J. Chem. Soc. Pak. 1992, 14(1), 24-34.

[23]. Salem, M. A. I.; Hamed, A. A.; El-Shekeil, A. G.; Babaqui, A. S.; Madkour, H. M. F. J. Chem. Soc. Pak. 1990, 12(3), 189-200.

[24]. Hamed, A. A.; Madkour, H. M. F.; Al-Nuaimi, I. S.; Hussain, B. A. Anales De Quimica de la Sociedad Espanola de Quimica (An Quim) 1994, 90(5-6), 359-364.

[25]. Weast, R. C. (Eds.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., pp. C-189.

[26]. Grayer, R. J.; Harbone, J. B. Phytochemistry 1994, 37, 19-42.
http://dx.doi.org/10.1016/0031-9422(94)85005-4

[27]. Irob, O. N.; Moo-young, M.; Anderson, W. A. Int. J. Pharmacog. 1996, 34, 87-90.
http://dx.doi.org/10.1076/phbi.34.2.87.13201

[28]. Jawetz, E.; Melnick, J. L.; Adelberg, E. A. Lang Medical publication, Los Altos, California 1974.

[29]. Muanza, D. N.; Kim, B. W.; Euler, K. L.; Williams, L. Int. J. Pharmacog. 1994, 32, 337-345.
http://dx.doi.org/10.3109/13880209409083012

[30]. El-Shaaer, H. M.; Perjessy, A.; Zahradnik, P.; Lacova, M.; Sustekova, Z. Monatsh. Chem. 1993, 124, 539-548.
http://dx.doi.org/10.1007/BF00819522

[31]. Jones, W. D. J. Chem. Soc. Perkin Trans 1 1981, 342-344.

[32]. Gasparova, R.; Lacova, M. Collect. Czech. Chem. Commun. 1995, 60(7), 1178-1185.
http://dx.doi.org/10.1135/cccc19951178

[33]. Rao, K. V. Ind. Eng. Chem. Res. 2002, 41, 3333-3334
http://dx.doi.org/10.1021/ie010771r

[34]. Ibrahim, S. S.; El-Shaaer, H. M.; Hassan, A. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 151-159.
http://dx.doi.org/10.1080/10426500210228

[35]. Sayeed, A. A.; Sami, S. M.; Ibrahim, S. S. Egypt J. Chem. 1977, 20, 225-233.

[36]. Budzisz, E.; Malecka, M.; Nawrot, B. Tetrahedron 2004, 60, 1749-1759.
http://dx.doi.org/10.1016/j.tet.2003.12.044

[37]. Schonberg, A.; Singer, E.; Sidky, M. M. Chem. Ber. 1961, 94, 660-668.
http://dx.doi.org/10.1002/cber.19610940313

[38]. Kiichi, I.; Nakajima, K. J. Heterocycl. Chem. 1988, 25(2), 511-515.
http://dx.doi.org/10.1002/jhet.5570250229

[39]. Kaleta, Z.; Makowski, B. T.; Soos, T.; Dembinski, R. Org. Lett. 2006, 8, 1625-1628.
http://dx.doi.org/10.1021/ol060208a
PMid:16597126

[40]. Varma, R. S.; Kumar, D. Org. Lett. 1999, 1, 697-700.
http://dx.doi.org/10.1021/ol990629a
PMid:16118866

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Department of Chemistry, Faculty of Science, Ain Shams University, Egypt
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