Nano-TiO2 an Efficient, Clean and Eco-friendly Catalyst for Synthesis of Naphthoxazinone Derivatives as High Potent Antibacterial Agents

Document Type: Original Article

Author

Department of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Abstract

Oxazines naturally occurs and synthetically exhibit wide-ranging biological activity. In this study, a highly practical and efficient of 1,2-dihydro-1-phenylnaphtho[1,2-e][1,3]oxazine-3-one derivatives was developed via a multi-component reaction of 2-naphthol, aldehydes and urea in the presence of nano-titanium oxide as solid, recyclable catalyst at one-pot and solvent-free conditions. These synthetic compounds 2a-e were evaluated as potential antibacterial agents. The structures of products were confirmed by spectral analysis FT-IR and 1H NMR. The antibacterial activity of the compounds was screened against Staphylococcus aureus and Escherichia coli. These results showed that these compounds exhibited significant to moderate activities against both Gram (+) and Gram (-) organisms. 

Keywords


1.Klayman D.L., Scovill J.P., Bartosevich J.F., Mason C.J., 1979. 2-Acetylpyridine thiosemicarbazones. 2. N4, N4-Disubstituted derivatives as potential antimalarial agents. J Med Chem. 22(11), 1367-1373.

2. Hermakens P.H.H., Otlenheijm H.C, Ress D.C., 1997. Solid-phase organic reactions II: A review of the literature Nov 95–Nov 96. Tetrahedron. 53(16), 5643-5678.

3.Dougherty K.J., Bannatyne B.A., Jankowska E., Krutki P., Maxwell D.J.J., 2005. Membrane receptors involved in modulation of responses of spinal dorsal horn interneurons evoked by feline group II muscle afferents. J Neuro Sci. 25(3), 584-593.

4. Anderluh M., Cesar J., Stefanic P., Kikelj D., Janes D., Murn J., Nadrah K., Tominc M., Addicks E., Giannis A., Stegnar M., Dolenc M.S., 2005. Design and synthesis of novel platelet fibrinogen receptor antagonists with 2H-1,4-benzoxazine-3(4H)-one scaffold. A systematic study. Eur J Med Chem. 40, 25.

5. Bethiel R., Cochran J., Moon Y.C., Suganthini Nanthakumar S., 2003. Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases. Patent Appl. US20030087922 A1.

6.Patel M., Ko S.S., McHugh R.J.J., Markwalder J.A., Srivastava A.S., Cordova B.C., Klabe R.M., Erickson-Viitanen S., Trainor G.L., Seitz S.P., 1999. Synthesis and evaluation of analogs of Efavirenz (SUSTIVA) as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem Lett. 9, 2805.

7. Habib O.M.O., Hassan H.M., El-Mekabaty A., 2012. Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity. Am J Organic Chem. 2(3), 45-51.

8. Johnson P.Y., Silver R.B., 1973. The synthesis and antitumor properties of a 6-Alkoxy tetrahydrooxazine. J Heterocycl Chem. 10, 1029-1030.

9. Lesher G.Y., Surrey A.R., 1955. A new method for the preparation of 3-substituted 2-oxazolidones. J Am Chem Soc. 77, 636-641.

10. Mosher H.S., Frankel M.B., Gregory M., 1953. Heterocyclic Diphenylmethane derivatives. J Am Chem Soc. 75(21), 5326-5328.

11. Ren H., Grady S., Gamenara D., Heinzen H., Moyna P., Croft S., Kendrick H., Yardley V., Moyna G., 2001. Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds. Bioorg Med Chem Lett. 19(11), 1851-1854.

12.Benedini F., Bertolini G., Cereda R., Dona G., Gromo G., Levi S., Mizrahi J., Sala A., 1995. New Antianginal Nitro Esters with Reduced Hypotensive Activity. Synthesis and Pharmacological Evaluation of 3-[(Nitrooxy)alkyl]-2H-1,3-benzoxazin-4(3H)-ones. J Med Chem. 38(1), 130-136.

13. Clark R.D., Caroon J.M., Kluge A.F., Repke D.B., Roszkowski A.P., Strosberg A.M., Baker S., Bitter S.M., Okada M.D., 1983. Synthesis and antihypertensive activity of 4'-substituted spiro[4H-3,1-benzoxazine-4,4'-piperidin]-2(1H)-ones. J Med Chem. 26(5), 657-661.

 14. Latif N., Mishriky N., Assad F.M., 1982. Carbonyl and thiocarbonyl compounds. XIX. Intramolecular cyclization of (2-nitroetheny1)aryl N-arylcarbamates : synthesis of newer series of 3,4-dihydro-2H-1,3-oxazin-2-ones and their antimicrobial activities. Aust J Chem. 35(5), 1037-1043.

15. Alkhathlan H.Z., 2003. Synthesis of 4-alkoxy-4-methyl- and 4-alkoxy-4-fluoromethyl-1,3-benzoxazinones. Tetrahedron. 59(41), 8163-8170.

16. Yadav L.D., Kapoor R. 2004. Novel Salicylaldehyde-Based Mineral-Supported Expeditious Synthesis of Benzoxazin-2-ones. J Org Chem. 69(23), 8118-8120.

17. Szatmari I., Hetenyi A., Lazar L., Fulop F., 2004. Transformation reactions of the betti base analog aminonaphthols. J Heterocycl Chem. 41(3), 367-373.

18. Cimarelli C., Palmieri G., Volpini E., 2004. A facile synthesis of 3, 4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and Grignard reagents Preparation of N-[1-(2′-hydroxyphenyl)alkyl]amides. Can J Chem. 82(4), 1314-1321.

19. Imani Shakibaei G., Khavasi H.R., Mirzaei P., Bazgir A., 2008. A three-component, one-pot synthesis of oxazinoquinolin-3-one derivatives. J Heterocyclic Chem. 45(5), 1481-1484.

20. Abbastabar Ahangar H., Mahdavinia G.H., Marjani K., Hafezian A., 2010. A one-pot synthesis of 1,2-dihydro-1-arylnaphto[1,2-e][1,3]oxazine-3-one derivatives catalyzed by perchloric acid supported on silica (HClO4/SiO2) in the absence of solvent. J Iran Chem Soc. 7(3), 770-774.

21. Taati M.R., Mamaghani M., Mahmoodi N.O., Loghmanifar A., 2009. A simple access to the synthesis of 5,6-dihydro-4H-1,3-oxazine under solvent free conditions and microwave irradiation. Transactions C: Chemistry and Chemical Engineering. 16(1), 17-21.

22. Mirzaei A., 2015. Catalyst free synthesis of new 1,3-oxazines from b-naphtol, aldehyde and ammonia. Iran. J Org Chem. 7(1), 1477-1479.

23.Hunnur R., Kamble R., Dorababu A., Sunil Kumar B., Bathula C., 2013. TiCl4: An efficient catalyst for one-pot synthesis of 1,2-dihydro-1-aryl-naphto-[1,2-e][1,3]oxazin-3-one derivatives and their drug score analysis. Arab J Chem. DOI: 10.1016/j.arabjc.2013.06.028

25 Montazeri N., Pourshamsian K., Rezaei H., Fouladi M., Rahbar S., 2013. Nano Fe3O4: A Novel and Magnetically Recyclable Catalyst for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles in Solvent-Free Conditions. Asian J Chem. 25(6), 3463-3466.

27. Pourshamsian K., 2015. ZnO-NPs as an efficient reusable heterogeneous catalyst for synthesis of 1,4-Dihydropyrimidine derivatives in solvent-free conditions. Int J Nano Dimension. 6(1), 99-104.

28. Kantevari S., Vuppalapati S.V.N., Bantu R., Nagarapu I., 2010. An efficient one-pot three component synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones using montmorillonite K10 under solvent free conditions. J Heterocyclic Chem. 47(2), 313-317.

29. Ahangar H.A., Mahdavinia G.H., Marjani K., Hafezian A., 2010. A one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e]oxazine-3-one derivatives catalyzed by perchloric acid supported on silica (HClO4/SiO2) in the absence of solvent. J Iran Chem Soc. 7(3), 770-774.

30. Chaskar A., Vyavhare V., Padalkar V., Phatangare K., Deokar H., 2011. An environmentally benign one-pot synthesis of 1,2-dihydro-1-aryl-3H-naphtho[1,2-e][1,3]oxazin-3-one derivatives catalyzed by phosphomolybdic acid. J Serbian Chem Soc. 76(1), 21-26.

31. Nizam A., Pasha M.A., 2010. Iodine-catalyzed, rapid and efficient, one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e]oxazine-3-ones under solvent-free conditions. Synt Commun. 40, 2864-2868.

32. Dabiri M., Delbari A.S., Bazgir A., 2007. A novel three-component, one-pot synthesis of 1,2-dihydro-1-aryl-naphtho[1,2-e][1,3]oxazine-3-one derivatives under microwave assisted and thermal solvent-free conditions. Synlett. 5, 821-823.

33. Dabiri M., Delbari A.S., Bazgir A., 2007. A simple and environmentally benign method for the synthesis of naphthoxazin-3-one derivatives. Heterocycles. 41(3), 543-548.

34. Kumar A., Saxena A., Dewan M., De A., Mozumdar S., 2011. Recyclable nanoparticulate copper mediated synthesis of naphthoxazines in PEG-400: a green approach. Tetra lett. 52(38), 4835-4839.

35. Nemati F., Beyzai A. 2013. A facile one-pot solvent-free synthesis of 1,2-dihydro-1-aryl-naphtho[1,2-e][1,3]oxazine-3-ones catalyzed by wet cyanuric chloride. J Chem. 2013, Article ID 365281, 4.

36. Pouramiri B., Tavakolinejad Kermani E. 2014. E_cient, three-component synthesis of 1-aryl-2,3-dihydro-3-phenyl-1H-naphth[1,2-e][1,3] oxazines derivatives, using LaCl3/ClCH2COOH as an environmentally benign and green catalytic system. Sci Iranica. 21(3), 703-707.

37. Ramazani A., Rouhani M., Mirhadi E., Sheikhi M., Slepokura K., Lis T. 2016. Perlite-SO3H nanoparticles as an efficient and reusable catalyst for one-pot three component synthesis of 1,2-dihydro-1-aryl-naphtho[1,2-e][1,3]oxazine-3-one derivatives under both microwave-assisted and thermal solvent-free conditions: single crystal X-ray structure analysis and theoretical study. Nano Chem Res. 1(1), 87-107.