Synthesis and Biological Evaluation of Novel Thiazolidinedione Analogues as 15-Hydroxyprostaglandin Dehydrogenase Inhibitors

Abstract

Novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitors were synthesized. Compounds 2, 3, and 4 exhibited IC(50) of 25, 8, and 19 nM, respectively. They also significantly increased levels of PGE(2) in A549 cells. To assess the influence of 15-PGDH inhibitor on cochlear blood flow (CBF), 2 was applied intravenously to guinea pigs. It increased their CBFs. Scratch wounds were also analyzed in confluent monolayers of HaCaT cells. Cells exposed to 4 showed significantly improved wound healing with respect to a control.

Diacetoxyiodobenzene mediated oxidative dethionation of N-substituted-5-arylmethylidene rhodanines: an efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones

“…Further, thiazolidine-2,4-diones derivatives have been reported as inhibitors of targets such as glycogen synthase kinase-3 (GSK-3), 7 aldose reductase, 8 Pim protein kinases 9 and 15-hydroxyprostaglandin dehydrogenase. 10 Because of the prominent biological activities of thiazolidine-2,4-dione derivatives, development of clean synthetic methods is of great significance.…”

Design and synthesis of a novel 5-(aminomethylene)thiazolidine-2,4-dione derivatives as potent hepatitis-B virus polymerase inhibitors

“…On the other hand, the thiazolidinedione analogues were investigated for the treatment of a variety of diseases, e.g., as anti-cancer (Havrylyuk et al, 2009), anti-HIV (Rawal et al, 2005), anti-ischemic (Adachi et al, 1999), anticonvulsant (Ergenç et al, 1994), antimicrobial (Piscopo et al, 1989), antihistaminic (Previtera et al, 1994;Diurno et al, 1999), and antidiabetic agents (Carroll et al, 2011;Bruno et al,2002), 15-hydroxy prostaglandin dehydrogenase inhibitors (Wu et al, 2011;Zidar et al, 2010), inhibitors of MurD ligase (Ha et al, 2012), aldose reductase inhibitors (Ma et al, 2012), for their anti-obesity effects (Bhattarai et al, 2010).…”

Synthesis and Evaluation of New 2-Iminothiazolidin-4-one and Thiazolidin-2,4-dione Derivatives as Antimicrobial and Anti-inflammatory Agents

“…Their different biological activities were reported [1,2]. Among the most important biological and pharmacological activities of both heterocyclic pharmacophoric moieties are: antihyperglycemic [3,4], antibacterial [5][6][7][8][9], antifungal [10,11], antiinflammatory [12][13][14][15][16][17], cyclooxygenase and lipoxygenase inhibitors [18,19], anticonvulsants [20,21], antitumor [22], antioxidant [23] and several other activities [1,2].…”