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Molecules 2017, 22(9), 1416; doi:10.3390/molecules22091416

Identification of Optically Active Pyrimidine Derivatives as Selective 5-HT2C Modulators

Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST), 5 Hwarangno 14-gil, Seongbuk-gu, Seoul 02792, Korea
Department of Chemistry, Korea University, Seoul 02841, Korea
Department of Chemical & Molecular Engineering/Applied Chemistry, Hanyang University, Ansan, Gyeonggi-do 15588, Korea
Department of Biological Chemistry, Korea University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea
Convergence Research Center for Diagnosis, Treatment and Care System of Dementia, KIST, Seoul 02792, Korea
Authors to whom correspondence should be addressed.
Received: 31 July 2017 / Revised: 22 August 2017 / Accepted: 23 August 2017 / Published: 26 August 2017
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues)
View Full-Text   |   Download PDF [993 KB, uploaded 26 August 2017]   |  


A series of pyrimidine derivatives 4ai were synthesized and evaluated for their binding affinities towards 5-HT2C receptors. With regard to designed molecules 4ai, the influence of the size of alkyl ether and the absolute configuration of a stereogenic center on the 5-HT2C binding affinity and selectivity was studied. The most promising diasteromeric mixtures 4d and 4e were selected in the initial radioligand binding assay and they were further synthesized as optically active forms starting from optically active alcohols 5d and 5e, prepared by an enzymatic kinetic resolution. Pyrimidine analogue (R,R)-4e displayed an excellent 5-HT2C binding affinity with good selectivity values against a broad range of other 5-HT receptor subtypes. View Full-Text
Keywords: pyrimidine; optically active; enzymatic kinetic resolution; 5-HT2C receptor; binding affinity; selectivity pyrimidine; optically active; enzymatic kinetic resolution; 5-HT2C receptor; binding affinity; selectivity

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Kim, J.; Jo, H.; Lee, H.; Choo, H.; Kim, H.J.; Pae, A.N.; Cho, Y.S.; Min, S.-J. Identification of Optically Active Pyrimidine Derivatives as Selective 5-HT2C Modulators. Molecules 2017, 22, 1416.

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