Design, synthesis and anticancer evaluation of novel thiazine, pyrimidine and pyridine derivatives

A. Ghoneim, Amira; G. Assy, Mohamed; Mohamed, Enaiat K.; Ragab, Islam

Document Type : Original Research Article

Authors

¹ Chemistry Department, Faculty of Science, Zagazig University, Zagazig, EG‐44519, Egypt

² Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egyp

³ Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt

Abstract

Acylisothiocyanate (1) was allowed to react with benzylidene malononitrile producing oxazine derivative (2). Also, compound (1) was reacted with sodium azide followed by refluxing with sodium ethoxide affording thiazinotetrazole derivative (4). The reaction of acetylacetone with compound (1) gave pyridine derivative (5) by intramolecular cycloaddition while it was reacted with N-methyl aniline affording thiazine derivative (7). In addition, it was reacted with cyanoacetamide producing mercaptopyrimidine derivative (9). Finally, compound (1) was refluxed with phenylhydrazine, urea, guanidinum carbonate and anthranilic acid in the presence of dry acetone affording triazole derivative (11), N-substituted pyrimidine (15), compound (18) and thiopyrimidine derivative (19) respectively. The structures of the new compounds were confirmed on the basis of elemental and spectral data. Some of the synthesized compounds were screened as anticancer.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] A.K. Mukerjee, R. Ashare, Chem. Rev., 1991, 91, 1-24.

[2] J.L. Jimenez Blanco, B. Sylla, C. Ortiz Mellet, J.M. Garcia Fernandez, J. Org. Chem., 2007, 72 , 4547-4550.

[3] N. Al-Masoudi, N.A Hassan, Y.A. Al-Soud, P. Schmidt, A.E.D.M. Gaafar, M. Weng, S. Marino, A. Schoch, A.A. Amer, J. C. Jochims, J. Chem. Soc.,Perkin Trans.,1998, 947-953.

[4] H. L. .Abd El-Mohdy, S.Ghanem, Biodegradability, J. Polym. Res.,2009, 16, 1–10.

[5] N.A. Abdel-hafez, A.M. Mohamed, , A.E. Amr, and Abdalla, M.M. , Sci. Pharm.,2009, 77, 539-553.

[6] B.A. Arthington, M. Motly, D.W. Warnok, C.J. Morrison, J. Clin. Microbiol,2000, 38, 2254-2260.

[7] S.A. Bahashwan, J. Pharm. Pharmacol., 2011, 5, 527-531.

[8] J.C. Boehm, K.L. Widdowson, J.F. Callahan, and Z. Wan, Patent Cooperation Treaty International Application, (2003), WO 2003088972.

[9] D.H. Boschelli, Z. Wu, S.R. Klutchko, Showalter, H.D., Hamby, J.M., Lu, G.H.,

Major, T.C., Elliott, W.L., Steinkampf, R., Bradford, L.A., Hallak, H. and Doherty, A.M., J. Med. Chem., 1998, 41, 4365-4377.

[10] M.B. Buddh, A.H. Bapodra, k.D. Ladva. , J. Chem., 2011, 4, 824-828.

[11] R.M. Butnariu, I.I. Mangalagiu, Bioorg. and Med. Chem., 2009, 17,2823-2829.

[12] M.B. El-Arnaouty, A.M. Abdel Ghaffar, H.M.El Shafey, J. Appl. Polym. Sci., 2008, 107, 744-754

[13] C.T. Edward, L. J. Bin, Org. Chem., 2003, 68, 9938-9947.

[14] A.B. Broom, J. L. Shim, G.L. Anderson, J. Org. Chem., 1976, 41, 1095-1099.

[15] C.G. Bonde, N. Gaikwad, J. Bioorg. Med. Chem., 2004, 12, 2151-2161.

[16] G. Kucukguzel, A. Kocatepe, E. DeClercq, F.Sahin, M. Gulluce, Eur. J. Med. Chem., 2006,41, 353-359.

[17] P. Vicini, A. Geroniki, K.. Anastasia, M. Incerti, Zani, F. Bioorg. Med. Chem., 2006, 14, 3859-3864.

[18] P. Skehan, D.R. Storeng, A.Scudiero, Monks, J.Mc.Mahon, D.Vistica, J.T. Warren, H.Bokesch, S. Kenney, M.R. Boyd, J. Natl. Cancer Inst. Monographs.,1990, 82,1107- 1112.

Iranian chemical communication

Design, synthesis and anticancer evaluation of novel thiazine, pyrimidine and pyridine derivatives

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 195-206

Design, synthesis and anticancer evaluation of novel thiazine, pyrimidine and pyridine derivatives

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15April 2017Pages 195-206

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 195-206