164520-90-5Relevant academic research and scientific papers
NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
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Page/Page column 10, (2011/11/12)
The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.
Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors
Wu, Ying,Karna, Sandeep,Choi, Cheol Hee,Tong, Min,Tai, Hsin-Hsiung,Na, Dong Hee,Jang, Chul Ho,Cho, Hoon
scheme or table, p. 5260 - 5264 (2011/10/09)
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 PGE2 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.
Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors
Wu, Ying,Tai, Hsin-Hsiung,Cho, Hoon
experimental part, p. 1428 - 1433 (2010/05/02)
Prostaglandins have a short life in vivo because they are metabolized rapidly by oxidation to 15-ketoprostaglandins catalyzed by a cytosolic enzyme known as NAD+-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, CT-8, a thiazolidinedione analogue, was found to be a potent inhibitor of 15-PGDH. Structure-activity analysis indicated that the N-methylation of thiazolidine-2,4-dione, CT-8, abolished the inhibitory activity, whereas the introduction of an ethyl hydroxyl group at amine in CT-8 still had a good inhibitory effect. Based on the structures of the thiazolidinediones analogues and inhibitory activity, a range of benzylidene thiazolidinedione derivatives were synthesized with different substituents on the phenyl ring and their inhibitory activity was evaluated. Replacement of the cyclohexylethyl group of CT-8 with the hetero five-member ring increased the inhibitory potency. However, replacement of the cyclohexylethyl group with a hetero six-member ring decreased the inhibitory potency significantly. It was found that compound 2 (5-(4-(2-(thiophen-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione) was the most potent inhibitor that was effective in the nanomolar range.
3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization
Duplantier, Allen J.,Efremov, Ivan,Candler, John,Doran, Angela C.,Ganong, Alan H.,Haas, Jessica A.,Hanks, Ashley N.,Kraus, Kenneth G.,Lazzaro Jr., John T.,Lu, Jiemin,Maklad, Noha,McCarthy, Sheryl A.,O'Sullivan, Theresa J.,Rogers, Bruce N.,Siuciak, Judith A.,Spracklin, Douglas K.,Zhang, Lei
scheme or table, p. 2524 - 2529 (2010/03/03)
The discovery, synthesis and SAR of a novel series of 3-benzyl-1,3-oxazolidin-2-ones as positive allosteric modulators (PAMs) of mGluR2 is described. Expedient hit-to-lead work on a single HTS hit led to the identification of a ligand-efficient and struct
