A Novel Bromonaphthyl Based 2-Amino-1,3-Thiazines: Synthesis, Characterization with Invitro Antimicrobial Screening

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A Novel Bromonaphthyl Based 2-Amino-1,3-Thiazines: Synthesis, Characterization with Invitro Antimicrobial Screening

Author Affiliations

¹PG and Research Department of Chemistry, Rajah Serfoji Govt. College, Thanjavur-613 005, Tamilnadu, INDIA

Res.J.chem.sci., Volume 5, Issue (7), Pages 8-11, July,18 (2015)

Abstract

A clinically important substrate of bromosubstituted acetylnaphthalene was used as the precursor for the preparation of a series of 1-(2-bromonaphthalen-6-yl)-3-phenylprop-2-en-1-ones. The formed unsaturated ketones on treatment with thiourea in the presence of base like KOH in alcohol yields corresponding 4-(2-bromonaphthalen-6-yl)-6-phenyl-6H-1,3-thiazin-2-amine. The synthesized thiazines are evaluated their structure on the basis of NMR, MASS, IR and Elemental analyses along with their physical data. The antibacterial and antifungal activities indicate some of these thiazines are potential antimicrobial agents.

References

Saranya A.V., Ravi S and Venkatachalapathi S., Invitro antioxidant activity of diethyl malonate adducts of phenothiazine, Res. J. Chem. Sci.,), 82-85 (2013)
Koketsu M., Tanaka K., Takenaka Y., Kwong C.D. and Ishihara H., Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents,Eur. J. Pharm. Sci.,15307-310 (2002)
Bozsing D., Sohar P., Gigler G. and Kovacs G., Synthesis and pharmacological study of new 3, 4-dihydro-2H, 6H-pyrimido-[2, 1-b][1, 3] thiazines, Eur. J. Med. Chem.,31, 663-668 (1996)
Florio S. and Leng J.L., Synthesis and reactivity of 4-substituted-2,3-dihydrobenzo-1,4-thiazines, J. Het. Chem.,19, 237-240 (1982)
Suarez M., Novoa H., Verdecia Y., Ochoa E., Alvarez A., Roberto R.,Alvarez M., Dolores M., Seoane C., Norbert M.B., Oswald M.P., Nazario M., A straight forward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-E][1,3]thiazines, Tetrahedron,62, 1365-1371 (2006)
Christophersen C., Secondary metabolites from marine bryozoans, Acta Chem. Scand., 69, 517-529 (1985)
Rathore M.M., Parhate V.V. and Rajput P.R., synthesis and antimicrobial activities of some bromo-substituted 1,3-thiazines, Int. J. Res. Pharm and Biomed. Sci., 59-62 (2013)
Bhanat K., Parashar B and Sharma V.K., Microwave induced synthesis and antimicrobial activities of various substituted pyrazolidines from chalcones, Res. J. Chem. Sci.,4(2), 68-74 (2014)
Bhale P.S., Dongare S.B. and Chanshetti U.B., Synthesis and antimicrobial screening of chalcones containing imidazo[1,2-a]pyridine nucleus, Res. J. Chem. Sci.,3(12), 38-42 (2013)
O'Brien P.J., Molecular mechanisms of quinone cytotoxicity, Chem. Biol. Interact,80(1), 1-4 (1991)
Ruy C.K., Choi K.U., Shim J.Y., You H.J., Choi I.H. and Chae M., Synthesis and antifungal activity of 6-arylthio-/6-arylamino-4,7-dioxobenzothiazoles, Bio org. Med. Chem., 11(18), 4003-4008 (2003)
Girdler R.B., Gore P.H. and Hoskins J.A., A re-examination of the Friedel–Crafts acetylation of 2-bromonaphthalene, J. Chem. Soc.(C) 518-520, (1966)

[ref1] Saranya A.V., Ravi S and Venkatachalapathi S., Invitro antioxidant activity of diethyl malonate adducts of phenothiazine, Res. J. Chem. Sci.,), 82-85 (2013)

[ref2] Koketsu M., Tanaka K., Takenaka Y., Kwong C.D. and Ishihara H., Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents,Eur. J. Pharm. Sci.,15307-310 (2002)

[ref3] Bozsing D., Sohar P., Gigler G. and Kovacs G., Synthesis and pharmacological study of new 3, 4-dihydro-2H, 6H-pyrimido-[2, 1-b][1, 3] thiazines, Eur. J. Med. Chem.,31, 663-668 (1996)

[ref4] Florio S. and Leng J.L., Synthesis and reactivity of 4-substituted-2,3-dihydrobenzo-1,4-thiazines, J. Het. Chem.,19, 237-240 (1982)

[ref5] Suarez M., Novoa H., Verdecia Y., Ochoa E., Alvarez A., Roberto R.,Alvarez M., Dolores M., Seoane C., Norbert M.B., Oswald M.P., Nazario M., A straight forward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-E][1,3]thiazines, Tetrahedron,62, 1365-1371 (2006)

[ref6] Christophersen C., Secondary metabolites from marine bryozoans, Acta Chem. Scand., 69, 517-529 (1985)

[ref7] Rathore M.M., Parhate V.V. and Rajput P.R., synthesis and antimicrobial activities of some bromo-substituted 1,3-thiazines, Int. J. Res. Pharm and Biomed. Sci., 59-62 (2013)

[ref8] Bhanat K., Parashar B and Sharma V.K., Microwave induced synthesis and antimicrobial activities of various substituted pyrazolidines from chalcones, Res. J. Chem. Sci.,4(2), 68-74 (2014)

[ref9] Bhale P.S., Dongare S.B. and Chanshetti U.B., Synthesis and antimicrobial screening of chalcones containing imidazo[1,2-a]pyridine nucleus, Res. J. Chem. Sci.,3(12), 38-42 (2013)

[ref10] O'Brien P.J., Molecular mechanisms of quinone cytotoxicity, Chem. Biol. Interact,80(1), 1-4 (1991)

[ref11] Ruy C.K., Choi K.U., Shim J.Y., You H.J., Choi I.H. and Chae M., Synthesis and antifungal activity of 6-arylthio-/6-arylamino-4,7-dioxobenzothiazoles, Bio org. Med. Chem., 11(18), 4003-4008 (2003)

[ref12] Girdler R.B., Gore P.H. and Hoskins J.A., A re-examination of the Friedel–Crafts acetylation of 2-bromonaphthalene, J. Chem. Soc.(C) 518-520, (1966)