Novel Route for Synthesis of Thiozolidine-2,4-Dione Derivatives as a Mannich Base
- 1 Department of Chemistry, Sri Krishnadevaraya University, Anantapur, India
- 2 Department of Chemistry, Sri Krishnadevaraya University, Anantapur, India
- 3 Department of Chemistry, Sri Krishnadevaraya University, Anantapur, India
Abstract
The Mannich base of Thiozolidine-2,4-dione derivatives has come to lime light due to their various pharmacological activities. Thiazolidine-2,4-dione is an extensively explored heterocyclic nucleus for designing of novel agents implicated for a wide variety of pathophysiological conditions, that is, diabetes, diabetic complications, cancer, arthritis, inflammation, microbial infection, and melanoma. In present work, synthesis quinoline attached imidazoline derivative using (3 + 2) cyclo-addition via imine of quinoline and TosMIC. These derivat ives were converted to Mannich bases of thiozolidine-2,4-dione using Knoevenagel condensation. The sulfonamide analogues of thiozolidine-2,4-Dione were also synthesized and characterized by using alkylation conditions.
- Vasincu, I.M., Apotrosoaei, M. and Panzariu, A.-T. (2014) Synthesis and Biological Evolution of New 1,3-Thiozolidine-4-one Derivatives of 2-(4-Isobutyl phenyl) Propionic Acid. Molecules, 19, 15005-15025.
- Chadha, N., Bahia, M.S., Kaur, M. and Silakari, O. (2015) Thiazolidine-2,4-Dione Derivatives: Programmed Chemical Weapons for Key Protein Targets of Various Pathological Conditions. Bioorganic & Medicinal Chemistry, 23, 2953-2974. https://doi.org/10.1016/j.bmc.2015.03.071
- Sharghia, H., Khalifeha, R., Moeinia, B.F., Beyzavia, M.H., Salimi Benic, A. and Doroodmand, M.M. (2011) Mannich Reactions of Secondary Amines, Aldehydes and Alkynes in Water using Cu/C Nanoparticles as a Heterogenous Catalyst. Journal of the Iranian Chemical Society, 8, S89-S103.
- Kapoor, A. and Khare, N. (2016) Antibacterial and Antifungal Evaluation of Mannich Bases of 2,4 Thiazolidinedione and Rhodanine. Der Pharmacia Lettre, 8, 143-148.
- Panzariu, A.-T., Aprotosoaei, M. and Profire, L. (2016) Synthesis and Biological Evaluation of new 1,3-Thiazolidine-4-one Derivatives of Nitro-l-Arginine Methyl Ester. Chemistry Central Journal, 10, 6.
- Shaikh, F.M., Patel, N.B. and Rajani, D. (2013) Synthesis of New Thiazolidine-2,4,Dione Derivatives & Their Antimicrobial & Antitubercular Activity. Indian Journal of Research in Pharmacy and Biotechnology, No. 1, 496-503.
- Prakash, D. and Bhoi, U.A. (2011) A Complete Review of Thiazolidine-4-One. Journal of Pharmacy Research, 4, 2436-2440.
- Previtera, T., Mervigorita, V. and Fenech, G. (1990) 3,3’-Di(1,3-Thiazolidine-4-One) System. Synthesis and Pharmacological Properties of 3,3’(1,2-Ethanediyl) Bis-(2-Hetero aryl-1,3-Thiazolidine-4-One) Derivatives. European Journal of Medicinal Chemistry, 25, 569-579.
- Patel, K.D., Patel, C.N. and Patel, G.M. (2016) Synthesis and Evaluation of Some New Thiazolidin-4-One Derivatives as Potential Antimicrobial Agents. Med-Chem (Los Angeles), 6, 10.
- Singh, T. and Khobragade, D. (2014) Synthesis and Evaluation of Thiazolidine-4-One for Their Antibacterial Activity. JPSBR, 4, 110-113.
- Bhaviskar, B.A., Khadabadi, S.S. and Deore, S.L. (2013) Microwave Assisted Synthesis and Diabetic Activity of Novel 5-[4-(Substituted) Benzylidine] Thiozolidine-2,4-Dione. Journal of Chemistry, 2013, Article ID: 656271.
- Primas, N., Verhaeghe, P., Cohen, A., Kieffer, C., et al. (2012) A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity. Molecules, 17, 8105-8117. https://doi.org/10.3390/molecules17078105