Synthesis, Characterization, and Antidiabetic Evaluation of Substituted 5-(2-Chloro-Quinolin-3-Ylmethylene)-Thiazolidine-2,4-Dione

Diabetes is a major public health problem that severely affects the quality of life of many people. The discovery of new antidiabetic agents remains the cornerstone for controlling this challenging disease in which heterocyclic compounds contributed greatly. Thiazolidinedione and quinoline nuclei exhibit different pharmacological potentials, the combination of these nuclei leads to the development of novel effective compounds. In this study, a series of substituted 5-(2-Chloro-quinolin-3-ylmethylene)-thiazolidine-2,4-dione (4a-h) derivatives were synthesized and characterized using different analytical instruments. These derivatives were evaluated for its anti-diabetic potentials at the dose of 30 mg/kg on streptozotocin-induced diabetic Wistar albino rat model. Among all the derivatives, compounds 3-[(2-Chloro-4-nitro-phenylamino)-methyl]-5-(2-chloro-quinolin-3-ylmethylene)-thiazolidine-2,4-dione (4e) and 5-(2-Chloro-quinolin-3-ylmethylene)-3-[(4-nitro-phenylamino)-methyl]thiazolidine-2,4-dione (4d) were shown excellent activity, compound 2-{[5-(2-Chloro-quinolin- 3-ylmethylene)-2,4-dioxo-thiazolidin-3-ylmethyl]-phenyl amino}-benzoic acid (4c) was shown moderate activity, in comparison to the activity of standard pioglitazone drug. Furthermore, this study on quinoline derivatives containing thiazolidinedione will surely help researchers to develop new antidiabetic agents with more potent activity.

Automated summary

The study synthesized and evaluated a series of quinoline derivatives with promising anti-diabetic potentials, especially compound 4e and 4d showing excellent activity. These compounds exhibited better activity compared to the standard drug pioglitazone, indicating the potential for developing new and more effective anti-diabetic agents.