Synthesis and Biological Evaluation of N-3-Alkyl-Thienopyrimidin-4-Ones as mGluR1 Antagonists
- Authors
- Kim, Minjoo; Kim, Youngjae; Seo, Seon Hee; Baek, Du-Jong; Min, Sun-Joon; Keum, Gyochang; Choo, Hyunah
- Issue Date
- May-2015
- Publisher
- 대한화학회
- Keywords
- mGluR1 Antagonist; N-3-Alkyl-thienopyrimidin-4-one; CNS disease; Neuropathic pain; Glutamate
- Citation
- Bulletin of the Korean Chemical Society, v.36, no.5, pp.1439 - 1451
- Indexed
- SCIE
SCOPUS
KCI
- Journal Title
- Bulletin of the Korean Chemical Society
- Volume
- 36
- Number
- 5
- Start Page
- 1439
- End Page
- 1451
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/18349
- DOI
- 10.1002/bkcs.10283
- ISSN
- 0253-2964
- Abstract
- Metabotropic glutamate receptor subtype 1 (mGluR1) is a potential target for the treatment of neuropathic pain, and there has been much effort to discover mGluR1 antagonists. In this study, a series of N-3-alkyl-thienopyrimidin-4-ones were prepared by introducing various alkyl and aryl groups to the N-3- and 7-positions of the thienopyrimidin-4-one core structure, respectively, and their inhibitory activities against mGluR1 were biologically evaluated. Structure-activity relationship study revealed that the trans-4-methylcyclohexyl, cycloheptyl, and cyclooctyl groups at N-3-position, and 2-fluorophenyl group at 7-position were most effective in potentiating the inhibitory activity of the thienopyrimidin-4-one derivatives against mGluR1. Among the synthesized compounds, 3-cyclooctyl-7-phenylthienopyrimidin-4-one and 3-cycloheptyl-7-(2-fluorophenyl)thienopyrimidin-4-one exhibited the most potent inhibitory activities with IC50 values of 115 and 107 nM, respectively.
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