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3Aryl2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl}-acrylic acid alkyl ester: synthesis and antihyperglycemic evaluation

3Aryl2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl}-acrylic acid alkyl ester: synthesis and antihyperglycemic evaluation,10.1007/s00044-010

3Aryl2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl}-acrylic acid alkyl ester: synthesis and antihyperglycemic evaluation   (Citations: 1)
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A number of 2,4-thiazolidinedione derivatives of aryl-substituted cinnamic acid were synthesized and studied for their antihyperglycemic activity in neonatal streptozotocin-induced diabetic Wister male rats. Substitution of the aryl ring resulted in higher activity. 3-(2,4-Dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl}-acrylic acid methyl ester (Thz7), was found to be most active compound in this series which showed that disubstitutions on aryl ring by electron releasing groups were found suitable for promising antihyperglycemic activity. Increase in the ester carbon chain length decreased the activity.
Journal: Medicinal Chemistry Research - MED CHEM RES , vol. 20, no. 6, pp. 678-686, 2011
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    • ...Thiazolidinediones (TZDs) are insulin-sensitizing agents that work by binding to PPAR-c, which leads to alteration in the expression of key regulators of glucose and lipid homeostasis genes (Hevener et al., 2001; Hammarstedt et al., 2005; Tontonoz and Spiegelman, 2008; Kumar et al., 2011; Mehendale-Munj et al., 2011)...
    • ...However, these drugs have liver, cardiovascular, hematological toxicity, and body weight gain associated side effects (Yildiz and Bozdag-Dundar, 2010; Kumar et al., 2011; Mehendale-Munj et al., 2011)...
    • ...Because different TZDs, as well as compounds with structures resembling the thiazolidinedione ring, carry comparable antidiabetic potentials, the thiazolidinedione ring is assumed to impart the antihyperglycaemic TZD action, whereas the substituted moieties seem to modulate pharmacokinetic and pharmacodynamic properties (Furnsinn and Waldhausl, 2002; Mourao et al., 2005; da Costa Leite et al., 2007; Yildiz and Bozdag-Dundar, 2010; Kumar et ...

    Tiago Gomes Araújoet al. Metabolic effects of benzylidene thiazolidinedione derivatives in high...

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