Novel Route for Synthesis of Thiozolidine-2,4-Dione Derivatives as a Mannich Base

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 derivatives 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.

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

“…To our best knowledge, the first Mannich base derived was from thiazolidinedione‐isatin conjugate candidate in 1985 and was evaluated for antileukemic activity [287] . Further, many studies were made to employ Mannich reaction in design of new antibacterial, [288] anticancer, antioxidant, [289,290] and antidiabetic agents [291,292] . Compound 261 (Figure 30), inspired by combretastatin, has shown significant selective antiproliferative activity against breast cancer.…”

“…[287] Further, many studies were made to employ Mannich reaction in design of new antibacterial, [288] anticancer, antioxidant, [289,290] and antidiabetic agents. [291,292] Compound 261 (Figure 30), inspired by combretastatin, has shown significant selective antiproliferative activity against breast cancer. Induction of apoptosis by upregulating pro-apoptotic agents and downregulation antiapoptotic agents, reduction of VEGF, HIF-1α expression, and decrease Akt and mTOR phosphorylation are the keys for its antiproliferative activity.…”