Synthesis and Biologically Activity of Novel 2- Chloro -3-Formyl -1,5-Naphthyridine Chalcone Derivatives

Subject Areas : Journal of Chemical Health Risks

Alaa I. Ayoob ¹ , Ghufran Th. Sadeek ² , Mohanad Saleh ^{3 *}

1 - New and Renewable Energies Department, College of Science, University of Mosul, Iraq
2 - Department of Chemistry, College of Education for Pure Science, University of Mosul, Iraq
3 - Department of Chemistry, College of Education for Pure Science, University of Mosul, Iraq

Received: 2021-09-01 Accepted : 2021-12-01 Published : 2022-01-01

Keywords: Chalcones, 1, 5-naphthyridine, Iodo chalcone, Dibromo chalcone,

Abstract :

A new and efficient procedure has been described for the synthesis of 2- chloro-1,5-Naphthyridine-3-carbaldehyde(1) from the condensation of N-(pyridine-3-yl) acetamide in presence of dimethylformamide and phosphorous oxychloride through Vilsmeir – Haack cyclization. The condensation of compound (1) with acetophenone, p-hydroxy acetophenone, pyridine-3-acetyl, furan-2-acetyl, and indole-2-acetyl in the presence of ethanolic sodium hydroxide through Claisen- Schmidt condensation give quinolinyl chalcones (2a-e) and it's further treated with dimethyl sulfoxide in the presence of iodine to obtained iodo chalcone compounds (3a-e). The smooth and selective bromination of chalcones (2a-e) affords dibromide compounds (4a-e). The structure of prepared compounds was identification by spectral and physical methods. Synthesized compounds (4a, 3e, 3b and 4e) give good biological activity from against Staphylococcus aureus and Staphylococcus epidermidis and moderate activity against Escherichia Coli and Proteus Vulgaris.

References:

1. Litvinov V.P., Roman S.V., Dyachenko V.D., 2000. Naphthyridines. Structure, physicochemical properties and general methods of synthesis. Russian Chemical Reviews. 69(3), 201-220.‏

 

2. Mogilaiah K., Prashanthi M., Kavitha S., 2006. Lithium chloride as an efficient catalyst for Friedlander synthesis of 1, 8-naphthyridines via the use of microwave irradiation and pestle/mortar.‏ Indian Journal of Chemistry. 45(B), 302-304.


3. Takahashi T., Hamada Y., Takeuchi I., Uchiyama H., 1969. Studies on chemotherapeutics. IV. Study of 1, 6-naphthyridine N-oxides. Yakugaku zasshi: Journal of the Pharmaceutical Society of Japan. 89(9), 1260-1265.‏


4. Kidwai M., Kohli S., 2001. Synthesis of dibenzo (b, g)-5-methyl-1, 8-naphthyridines.‏ ‏Indian Journal of Chemistry. 40(B), 248-249.


5. Bhat B.A., Sahu D.P., 2004. One Pot Synthesis of 4 (3 H) - Quinazolinones. Synthetic Communications. 34(12), 2169-2176.


6. Majumdar K.C., Taher A., Kumar Nandi R., 2012. Synthesis of heterocycles by domino-Knoevenagel-hetero-Diels-Alder reactions. Tetrahedron (Oxford. Print). 68(29), 5693-5718.


7. Ramesh S., Gaddam V., Nagarajan R., 2010. A flexible approach to the chromenoquinolines under copper/lewis acid catalysis. Synlett. 2010(05), 757-760.‏


8. Wei C., Li Z., Li C.J., 2003. The first silver-catalyzed three-component coupling of aldehyde, alkyne, and amine. Organic Letters. 5(23), 4473-4475.‏


9. Alonso C., Gonzalez M., Palacios F., Rubiales G., 2017. Study of the hetero-[4+ 2]-cycloaddition reaction of aldimines and alkynes. Synthesis of 1, 5-naphthyridine and isoindolone derivatives. The Journal of Organic Chemistry. 82(12), 6379-6387.‏


10. Kumar P., Aggarwal T., Verma A.K., 2017. Chemoselective Azidation of o-Alkynylaldehydes over [3+ 2] Cycloaddition and Subsequent Staudinger Reaction: Access to Benzonaphthyridines / Naphthyridines. The Journal of Organic Chemistry. 82(12), 6388-6397.‏


11. Maji P.K., Mahalanobish A., 2018. Efficient one pot synthesis of chromenonaphthyridine derivatives by CuI/InCl3 catalyzed aza Diels-Alder reaction. Heterocycles. 96, 43-49.‏


12. Heidarnezhad Z., Ganiev I., Obidov Z., Heidarnezhad F., Sharifi M.S., 2012. A Theoretical Study of NBO Analysis and Solvation Effects on Tautomerism Stability of 4, 8-dioxygenated 1, 5-naphthyridine. Orient. J Chem. 28(4), 1597-1604.‏


13. Friedrichsen, W., Katritzky, A. R., Rees, C. W., & Scriven, E. F. V. (1984). Comprehensive Heterocyclic Chemistry. By AR Katritzky and CW Rees, Pergamon Press, New York. 973-983.‏


14. Dave S.S., Ghatolea A.M., Rahatgaonkar A.M., Chorghade M.S., Chauhan P.M.S., Srivastava K., 2009. Experimental and computational evaluation of new quinolinyl chalcones as potent antiplasmodial agents.‏ Indian Journal of Chemistry. 48(B), 1780-1793.


15. Aldahham B.J., Al-Khafaji K., Saleh M.Y., Abdelhakem A.M., Alanazi A.M., Islam M.A., 2020. Identification of naphthyridine and quinoline derivatives as potential Nsp16-Nsp10 inhibitors: a pharmacoinformatics study. Journal of Biomolecular Structure and Dynamics. 1-8.‏


16. Saleh M.Y., Ayoub A.I., 2014. Synthesis of new derivatives of 2-chloro-3-formyl-1, 8-naphthyridine. European Journal of Chemistry. 5(3), 475-480.‏


17. Sdeek G.T., Mauf R.M., Saleh M.Y., 2021. Synthesis and Identification of some new Derivatives Oxazole, Thiazole and Imidazol from Acetyl Cysteine. Egyptian Journal of Chemistry. 64(12), 7465-7471.‏


18. Bouraiou A., Menasra H., Debache A., Rhouati S., Belfaitah A., 2006. Synthesis of some functionalized quinolyl aziridine derivatives. Journal-Societe Algerienne De Chimie. 16(2), 171.‏


19. Abbas A.M., Mohammed Taib A.S., Saeed N.H., 2020. Synthesis and Characterization of Linear Thermally Stable polyester contain Schiff Bases. Egyptian Journal of Chemistry. 63(8), 45-52.‏


20. Bawa S., Kumar S., 2009. Synthesis of Schiff’s bases of 8-methyl-tetrazolo [1, 5-a] quinoline as potential anti-inflammatory and antimicrobial agents.‏ Indian Journal of Chemistry. 48(B), 143-145.


21. Saleh M., Ayoub A.I., Hammady A.O., 2020. Synthesis biological studies of some new heterocyclic compound derived from 2-chloro-3-formyl quinoline and 4-(benzyl sulfonyl) acetophenone.  Egyptian Journal of Chemistry. 63(12), 4769 - 4776.‏


22. Karaman I., Şahin F., Güllüce M., Öǧütçü H., Şengül M., Adıgüzel A., 2003. Antimicrobial activity of aqueous and methanol extracts of Juniperus oxycedrus L. Journal of Ethnopharmacology. 85(2-3), 231-235.‏


23. Banoon, S., Ali, Z., & Salih, T. 2020. Antibiotic resistance profile of local thermophilic Bacillus licheniformis isolated from Maysan province soil. Comunicata Scientiae. 11, e3921-e3921.‏