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Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors
- Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors
- Bae, Yun Soo; Choi, Sun; Park, Jung Jae; Joo, Jung Hee; Cui, Minghua; Cho, Hyunsung; Lee, Won Jae; Lee, Sang Hyup
- Ewha Authors
- 배윤수; 최선; 주정희
- SCOPUS Author ID
- 배윤수; 최선; 주정희
- Issue Date
- Journal Title
- BIOORGANIC & MEDICINAL CHEMISTRY
- 0968-0896; 1464-3391
- vol. 24, no. 18, pp. 4144 - 4151
- Thiohydantoin; Benzylidene; Aluminum chloride; NADPH oxidase (NOX)
- PERGAMON-ELSEVIER SCIENCE LTD
- SCI; SCIE; SCOPUS
- We report the synthesis of novel 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins 3, and their biological evaluation using NADPH oxidase (NOX) 1 and 4. Based on structural and pharmacophore analyses of known inhibitors such as hydroxypyrazole 2, we envisioned interesting 2-thiohydantoin compounds, 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins 3 that would be expected to well match the structural features in 2. Efficient synthesis of eighteen target compounds 3 were achieved through the synthetic pathway of 4 -> 11 -> 3, established after consideration of several plausible synthetic pathways. The inhibitory activities of compounds 3 against NOX 1 and 4 were measured, with some of the target compounds showing similar or higher activities compared with reference 2; in particular, compounds 3bz, 3cz, and 3ez were found to be promising inhibitors of both NOX 1 and 4 with modest isozyme selectivities, which highlights the significance of the 2-thiohydantoin substructure for inhibition of NOX 1 and 4. This marks the first time these compounds have been applied to the inhibition of NOX enzymes. (C) 2016 Elsevier Ltd. All rights reserved.
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