Document Type : Research Paper

Authors

1 Department of Chemistry , Faculty of Science, University of Anbar, Alanbar ,Iraq

2 Department of Organic Chemistry , Faculty of Science, University of Ain Shams ,Cairo,

3 Department of Organic Chemistry , Faculty of Science, University of Ain Shams ,Cairo, Egypt

Abstract

The present work describes convenient synthesis of the novel Schiff bases 4, 5 and 6 by reaction of each of the previously synthesized quinazolinones 1, 2 and 3 with p-methoxybenzaldehyde. [2+2] Cycloaddition Reaction of the former Schiff bases within phenylisothiocyanate affording azatedine derivatives 7 and 8. Also, the quinazolines 1 and 2 could be reacted with α-bromoglucose tetraacetate giving peracetylated N-glycosides of quinazolinones 9 and 10 which were then deacetylated to afford N-glycosylated quinazolinones 11 and 12 respectively. On the other hand, Dapsone was reacted with p-methoxyacetophenone to afford 4-[(4-aminophenyl) sulfonyl]-N-[(1E)-1-(4-methoxyphenyl)ethylidene]aniline 15 which was, in turn, reacted with 4-chloro-2-ethoxyquinazoline 16 affording Schiff base 17. The latter was reacted with 2-furoyl chloride affording Schiff base 18. The structures of the novel Schiff bases and N-glycosides were confirmed by the IR, 1H-NMR, 13C-NMR, MS and elemental analysis. The antimicrobial activity for these synthesized compounds could outline, the moderate activity was observed  with new quinazoline compounds which proved to possess marked activity against E. coli, S. aureus and C. albicans. The strong activity has observed nearly with the most synthesized compounds .

Keywords

Main Subjects

1-   Jain, R. P., and Vederas, J. C.; Bioorg. Med. Chem. Lett., 14, 3655, (2004).
2-   Xu, Y., Guo, Q; Heterocycl, 63, 903,(2004).
3-   Strappaghetti, G., Brodi, C., Giannaccini, G., Betti, L.; Bioorg. Med. Chem. Lett. , 16, 2575,(2006).
4-   Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katrizky. A.R., Rees, C.W. Scriven, E. V.,Eds.; Elsevier: Oxford, , 2, 207,(1996).
5-   El-Shamy I. E., Abdel-Mohsen A.M., Alsheikh A. A., Fouda M. G., Al-Deyab S. S. , El-Hashash M. A. , Jancar J.; Dyes and Pigments  , 113,  357,(2015).
6-  Wagdy M. E., Hany S. I.,  Hatem A. A., Noha N. F., Mohieldin M. Y.; Euro. J. Med. Chem., 89 549, (2015).
7-  Alo-Asser, F.; Zelenin, K.N.; Lesiovskaya, E. E.; Bezhan, I. P.; Chakchir, B.A. Pharm. Chem. J., 36, 598,(2002).
8-  Jain , R. P.; Vederas, J. C.; Bioorg.Med.Chem.Lett., 14 , 3655,(2004).
9-  Carling, R. W.; Moore, K. W.; Street, L. I.; Wild, D.; Isted, C.; Leeson, P. D.; Thomas, S.; O-Conner, D.; Mc-Kernan, R. M.; Quirk, K.; Cook, S. M.; Atack, J. R.; Waftord, K. A.; Thompson, S. A. Dawson , G. R.; Ferris, P. Castro, J. I. J. Med. Chem., 47, 1807,(2004).
10-   Grasso, S.; De-Sarro, G.; Micale, N.; Zappala, M.; Puia, G.; Baraldi, M.; Demicheli, C. J. Med. Chem., 43, 2851, (2000).
11-    Haikal, A., El-Ashry, E., Banoub, J.; Carbohydr. Res., 338, 2291, (2003).
12-   Kim, J.S., Lee, H., Suh, M., Choo, H. P., Lee, S.K., Park, H.J.; Bioorg. Med. Chem., 2004, 12, 3683.
13-   Demirayak, S., Karaburun, A., Beis, R., Eur. J. Med. Chem., , 39, 1089,(2003).
14-   Johsen, M., Rehse, K., Petz, H., Stasch, J., Bischoff, E., Arch. Pharmacol., 336, 591,(2003).
15-   Lenz, E., Wilson, I., Wright, B., Partidge, E., Roddgers, C., Haycock, P.R.; Pharm. Biomed. Anal., 28, 31,(2002).
16-   Olmo, E., Armas, M., Lopez-perez, J., Ruiz, G., Vagas, F., Gimenez, A.; Bioorg. Med. Chem. Lett., 11, 2755,(2001).
17-   Dogruer, D., Kupeli, E., Yesilada, E., Sahin, M., Arch. Pharmacol., 337, 303,(2004).
18-   Kh.M.Shakhidoyatov,in Azotistye deterotsikly I alkaloidy [ Nitrogen Heterocycles and Alkaloids],Eds V.G.Kartsev,G.A.Tolstikov,Iridium-Press,Moscow,186(in Russian),(2001).
19-   Zhang Z.Y., Chu C.H., Hui X.P.: Ind. J. Chem. 41B, 2176. (2002)
20-   Singh H., Srivastava M.K., Singh B.K., Singh S.K., Dubey G.: Ind. J. Chem. 40B, 159. (2001)
21-   Mogilaiah K., Sakram S.: Ind. J. Chem. 43B, 20 14. (2004)
22-   Ajitha M., Rajnarayana K., Sangarapani K.: Pharmazie 57, 796. (2002)
23-   Bhatk,S.,Karthikeyan,M.S.,Holla,B.S.,Shetty,N.S.:Ind.J.Chem.43B, 1765, (2004)
24-   Aboraia A.S., Rahman H.M.R., Mahfouz N.M., Gendy A.E.L.: Bio-org. Med. Chem. 14, 1236, (2006)
25-   Saxena S., Verma M.: Ind. J. Pharm. Sci. 54, 1 (1992)
26-   D. Mullican, M.W. Wilson, D.T. Cannor, C.R. Kostlan, D.J. Schirier,  R. D. Dyer: J. Med. Chem. 36, 1090(1993)    
27-   P. Mishra, K. Joshi : Ind. J. Physiol. Pharmacol. 36, 347. (1992)
28-   A. M. F. Eissa, A. M. Elmetwally, M. A. Elhashash, A. M. Elgohary; J.Korean Chem.Soc.52, 3, 2008.
29-   A. F. Fahmy, M., M. A. El-Hashash, M. M. Habishy, S. Nassar, J. Revue Roumaine de Chimie,23, 11-12 (1567). (1978).
30-    M. A. El-Hashash, K. M. Darwish, S. A. Rizk, F. A. El-Bassiouny; The Uses of 2-Ethoxy-4(H)-3,1-benzoxazin-4-one in the Synthesis of Some quinazolinone derivatives of antimicrobial Activity.pharmaceuticals,4,1032-1051(2011).M. A. El-Hashash, K . M..Darwish,S . A. Rizk, F. A. El-Bassiouny;  The reactivity of 2-Ethoxy-4-Chloroquinazoline and Its Use in Synthesis of Novel Quinazoline Derivatives ; Organic .Chem. Intern. 2011 ;doi;10.1155 /2011/295491.
31-    Freddy H. Havaldar , Abhay R. Patil,  Syntheses of 1, 2, 4 Triazole   Derivatives  and their Biological Activity, E-Journal of Chemistry, CODEN ECJHAO ISSN:  09734945;5,.2,.347354,(2008).
32-   Bing Chai,XuhongQian,Song Cao,Haidong Liu,Gonghua Song,Synthesis and insecticidal of 1,2,4-triazole derivatives,ARKIVOC(II)141-145(2003)
33-   S.I.El-Nagdy, M.A.El-Hashash, A.S.El-Badaway, Synthesis of New 4(3H)-Quinazolinone derivatives. Egypt. J.Chem.49,6,721-730,(2006)
34-   M.S.Amine, M.A.El-Hashash, I.A.Attia; Synthesis and reaction of 2-ethoxy carbonyl-4(3H)-quinazolinone with nitrogen nucleophiles, Indian J.Chem.32B,577,(1993).
35-    M. A. El-Hashash, S . A. Rizk, F. A. El-Bassiouny, K . M..Darwish; Syntheses of Novel Schiff bases and N-Nucleosides Bearing 2-Ethoxy quinazolin-4(3H)-one-3-yl or 2-Ethoxy quinazolin-4-yl Moieties, Int. J. Chem. Sci.  Tech. (ISSN: 2248-9797) Volume 1-Issue4, 150-157, (2011)
36-   M.  A.  El-Hashash, D. B. Guirguis, M. A. Kadhim;  J of American Science  9, 12, (2013).
37-   M. A. El-Hashash,  S. A. Rizk, Nessim M.I.; Utility of Benzimidazoles in Synthesis of New Bases of Nucleoside Moieties, and as Antioxidant in Lubricant Oils; J Chem Eng Process Technol, 4:6, (2013).
38-   M. A. El-Hashash, S. A. Rizk, A. Y. El-Kady, A. M. Khalifa; Design, Synthesis and Structural Characterisation of Some Phthalazin-1(2H)-one Derivatives as reactive dye, anticorrosive, and antimicrobial nucleosides; J. Braz. Chem. Soc.(Accepted) (2015).
39-   M. A. El-Hashash, S. A. Rizk, Sythesis of Some New Quinazolin-4-one Derivatives and Evaluation of Their Antimicrobial effects;Egypt. J. Chem. 54, 4,  (2011).
40-   M. A. El-Hashash, S. A. Rizk, F. A. El-Bassiouny, K . M. Darwish; Uses of 2-Ethoxy-4(3H) quinazolinone in Synthesis of Quinazoline and Quinazolinone Derivatives of Antimicrobial Activity: The Solvent Effect, Global J.  Health  Sci.4(1)( 2012).
41-   M. A. El-Hashash, S. A. Rizk, Synthesis and Utility of 6-phthalimidoethyl-2(methyl /phenyl)benzoxazin-4-one in some heterocyclic synthesis; Mid. E. J. Sci. Res.11(4), 541, (2012).
42-   C. R. Johnson, S. K. Gorla, M. Kavitha , M. Zhang, X. Liu, B. Striepen, J. R. Mead, G. D. Cuny, L. Hedstrom; Phthalazinone inhibitors of inosine-50-monophosphate dehydrogenase from Cryptosporidium parvum;  Bioorganic & Medicinal Chemistry Letters 23, 1004 (2013).