Preparation of 2-sub stitutedphenyl-3-bis-2,4-(methylphenyl, 4-amino) -s-triazine-6-ylaminobenzoylamino-5-H-4- thiazolidinone Computational Studies of PC Model
Author Affiliations
- 1Department of Chemistry, Dr. H.S. Gour Central University Sagar, MP-470 003, INDIA
Res.J.chem.sci., Volume 3, Issue (10), Pages 24-30, October,18 (2013)
Abstract
Thiazolidinones have been shown to have various important therapeutic activities such a antifungal, antibacterial, anticonvulsant, anti-HIV, insecticidal, tuberculostatic and antiviral agents etc. sulfathiazole is an importance bacteriostatic sulfadrug, acetazolamide and methazolamide are power diuretics and all these are thiazole derivatives. Vitamin-B1 (thiamine) is an important thiazole derivative which is used in Beriberi. The reaction of p-toluidine and cyanuric chloride in dioxane gave 2-(4'-methyl phenyl amino) s-triazine (I). The reaction of compound (I) with p- toluidine in dioxane gave bis - 2,4-(4’-methyl phenyl amino)-s-triazine (II). The compound (II) was treated with ethyl p-amino benzoate in dioxane gave bis 2,4-(4’-methyl phenyl amino)–s-triazine-6-yl-aminoethylbenzoate (III). The compound (IV) bis-2,4-(4’- methylphenylamino)-s-triazine-6-ylaminobenzoylhydrazone was obtained by reaction of compound (III) with hydrazine hydrate in dioxane. A mixture of compound (IV) and different aromatic aldehydes in dioxane were refluxed which yielded bis-2,4 (4’-methylphenylamino)-s-triazine-6-ylaminobenzoyl substituted benzylhydrazone (V). The compound (V) was refluxed with thioglycolic acid which gave 2-substituted phenyl-3-bis-2,4-(4’-methylphenylamino)-s-triazine-6- ylaminobenzoylamino-5-H-4- thiazolidinone.
References
- Knapp S. and Levorse A.T., Tetrahedron Lett., 28, 3213- 3216 (1987)
- Dwievedi V. and Agarwal R.K., J. Asian Chem., 4, 180, (1992)
- Solanki A and Kishore K., J. Asian chem., 1, 177, (1994)
- Choudari B. R., shinde D.B. and shingare M.S., J. Asian Chem. 7, 832, (1995)
- Kudari S.M., Sangamesh and Badiger J. Ind. Chem., 9, 95 (1999)
- Clark H.T., Johnson J.R. and Robinson R., The Chemistry of Pemicillin, 447, (1949)
- Myung J., Oh and Jea P. Kim, Dyes and Pigments, 70, 220-225, (2006)
- Agarwal A., Srivastava K., Puri S.K. and Prem M.S., Bioorg. S. Med. Chem. Letters, 12, 531 (2005)
- Mulkwad V.V and Atul C., Chaskar, J. Ind. Chem., 458, 1710-1715 (2006)
- Baldaniya B.B. and Patel P.K., E-Journal Chem. 6 (3), 673-680, 2009.
- Raval J.P., International J. chem. Tech Res. Vol. No. 3, 616-620, 2009.
- Mehta MA., Singer N.P.S., et al; J. Ind. Phorm. Science, 68, 1, 103, 2006.
- Ashok Kumar, Chatrasal Singh Rajput et al. Bioorg. Med. Chem. 15, 3089, 2007.
- Anjali S., Kishor K., et al. J. Asian Chem. 15, 33, 2000.
- Mulwad V.V. and Shirodhar J.M., J. Ind. Heterocyclic. Chem. 11(4), 291, 2002.
- Parikh H.H., Parekh K.A. and Parikh A.R., Journal of Sciences Islamic Rupublie of Iran 15 (2), 143-148, 2004.
- Patel N.B., and Patel S.D., Acta Poloniac Pharmaceutica - Drug Res., 67(1), 45-53, (2010)
- Somia Bouriroura Organic Communications ACG Publications, 8, 14 (2010)
- Sekhar K.V.G.C., Sambasiva Rao V., Bull. Korean Chem. Soc., 31(5), 1219 (2010)
- Patel R.B., Desai P.S., Desai K.R., chikhalia K.H., J. Ind. Chem., 45B, 773, 778 (2006)