European Journal of Chemistry

Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines



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Fatin Ismail Hanafy

Abstract

Some new pyrido[2,3-d]pyrimidine derivatives (3a-c) were synthesized from 2-amino-5-cyano-6-methoxy-4-(4-methoxyphenyl)pyridine-3-carboxamide. 7-methoxy-5-(4-methoxy phenyl)-4-oxo-2-phenyl-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3b) and 7-met-hoxy-5-(4-methoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3c) are used in synthesizing 7a,b, then 8a,b. 7-methoxy-5-(4-methoxyphenyl)-2-methyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3a) and 4-hydrazinyl-7-methoxy-5-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile (8b) were condensed with different carbonyl compounds to produce compounds 4, 5, 6 and 9, 10, 11, 12. 3-Methoxy-1-(4-methoxyphenyl)-6-phenyl-7-hydropyridino[2,3-d]1,2,3,4-tetrazolo[1,5-e]pyrimidine-2-carbo-nitrile (13) was synthesized from 8a or 7a. Condensation of 8b with acetophenone to yield 14, which on further reaction gave 15 then 16. 4-Hydrazinyl-7-methoxy-5-(4-methoxyphenyl)-2-phenylpyrido[2,3-d]pyrimidine-6-carbonitrile (8a) also condensed with 4-amino antipyrine giving 17 then 18. Structures of these compounds have been deduced upon the basis of elemental analysis and spectral data. Significant antifungal activities were observed for some of the synthesized compounds.

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Hanafy, F. I. Synthesis and Antifungal Activity of Some New pyrido[2,3-d]pyrimidines. Eur. J. Chem. 2011, 2, 65-69.

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References

[1]. Burova, O. A.; Bystrykova, I. D.; Smirnova, N. M.; Safonova, T. S. Chem. Heterocyc. Comp. 1991, 27, 394-398.
doi:10.1007/BF00480837

[2]. Rahman, L. K. A.; Chhabra, S. R. Med. Res. Rev. 1988, 8, 95-155.
doi:10.1002/med.2610080106
PMid:3278183

[3]. Gangjee, A.; Vasudevan, A.; Queener, F.; Kisliuk, R. J. Med. Chem. 1996, 39, 1438-1446.
doi:10.1021/jm950786p
PMid:8691474

[4]. Zink, M.; Lanig, H.; Troschutz, R. Eur. J. Med. Chem. 2004, 39, 1079-1088.
doi:10.1016/j.ejmech.2004.09.001
PMid:15571870

[5]. Cordeu, L.; Cubedo, E.; Bandres, E.; Rebollo, A.; Saenz, X.; Chozas, H.; Dominguez, M.; Echeverria, M.; Mendivil, B.; Sanmartin, C.; Palop, J.; Font, M.; Foncillas, J. Bioorg. Med. Chem. 2007, 15, 1659-1669.
doi:10.1016/j.bmc.2006.12.010

[6]. Monge, A.; Martinez, V.; San Martin, C.; Simon, M. A. Spanish Patent ES 1994 2, 056, 742. [Chem. Abstr. 1995, 122, 105912q].

[7]. Parmar, K.; Suthar, B.; Suthar, A.; Maheta, A. J. Heterocycl. Chem. 2009, 46, 975-679.
doi:10.1002/jhet.190

[8]. Koeckkritz, P.; Ruhmann, C.; Fieblinger, D.; Schroeder, C.; Joksch, B.; Heider, B.; Weiher, B. Liebscher J. Ger. Offen. DE 4, 117, 802 [Chem. Abstr. 1993, 118, 191550s].

[9]. Narayana, B.; Ram Rao, A.; Shanthan Rao, P. Eur. J. Med. Chem. 2009, 44, 1369-1376.
doi:10.1016/j.ejmech.2008.05.025
PMid:18603332

[10]. Kanth, S.; Reddy, G.; Kishore, K.; Shanthan Rao, P.; Narsaiah, B.; Murthy, U. Eur. J. Med. Chem. 2006, 41, 1011-1016.
doi:10.1016/j.ejmech.2006.03.028
PMid:16766088

[11]. El-Subbagh, H. I.; Abuzaid, S. M.; Mahran, M. A.; Badria, F. A.; Al-Obaid, A. M. J. Med. Chem. 2000, 43, 2915-2921.
doi:10.1021/jm000038m
PMid:10956199

[12]. Ashalatha, B. V.; Narayana, B.; Vijaya Raj, K. K.; Suchetha Kumari, N. Eur. J. Med. Chem. 2007, 42, 719-728.
doi:10.1016/j.ejmech.2006.11.007
PMid:17189665

[13]. Seada, M.; El-Behairy, M. A.; Jahine, H.; Hanafy, F. Orient. J. Chem. 1989, 5, 273-280.

[14]. Chan, J.; Gustin, D.; Divirgilio, E. S.; Guram, A.; Faul, M. M. Synthesis 2007, 23, 3678-3682.
doi:10.1055/s-2007-990878

[15]. Seada, M.; Abdel-Rahman, R. M.; El-Behairy, M.; Hanafy, F. Asian J. Chem. 1992, 4, 604-614.

[16]. Okafor, C. O. J. Org. Chem. 1973, 38, 4386-4390.
doi:10.1021/jo00965a008

[17]. Dehuri, S. N.; Pradhan, P. C.; Nayak, A. J. Indian Chem. Soc. 1983, 60, 475-481.

[18]. Seada, M.; Abdel-Rahman, R. M.; Hanafy, F. J. Indian Chem. Soc. 1992, 69, 882-884.

[19]. Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H. J.; Voelter, W. Arzneim-Forsch. 2000, 50, 915-922.
PMid:11105234

[20]. Rahman, A. U.; Choudhary, M. I.; Thomsen, W. J. “Bioassay Techniques for drug development, 16 the Netherlands”: Harwood Academic Publishers 2001.
doi:10.4324/9780203304532

[21]. Jorgensen, J. H.; Crawford, S. A.; Mc Elmeel, M. L.; Fiebelkorn, K. R. J. Clin. Microbiol. 2004, 42, 1800-1802.
doi:10.1128/JCM.42.4.1800-1802.2004
PMid:15071055 PMCid:387617

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