Synthesis of Novel 4(5)-(5-Aminotetrahydropyran-2-yl)imidazole Derivatives and Their in Vivo Release of Neuronal Histamine Measured by Brain Microdialysis
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概要
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The (2R,5S)-trans- and (2S,5S)-cis-stereoisomers 1a and 1b of 4(5)-(5-aminotetrahydropyran-2-yl)imidazole, which have two chiral centers and adopt a stable chair conformation, were synthesized via cyclization of diol in termediates 7 using L-glutamine as the starting material. Their enantiomers, (2S,5R)-trans-1c and (2R,5R)-cis-1d, were synthesized by the same methodology from D-glutamine. Stereo isomers 1a-d were converted into cyanoguanidines 1la-d, and into N-isopropyl and N-3,3-dimethylbutyl derivatives 12a-d and 13a-d, respectively. The results of in vivo brain microdialysis of the derivatives apparently indicated that only (2S,5R)-isomers increased the release of neuronal histamine. Among the many (2S,5R)-N-alkyl derivatives, 13c (OUP-133) and 18 (OUP-153) increased histamine release to 180-190% and 180-200% of basal levels, respectively, and were found to be novel histamine H_3 antagonists.
- 2007-08-01
著者
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FUJITA Takeshi
Department of Dental and Biomedical Materials Science, Unit of Basic Medical Sciences, Graduate Scho
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Kawamura M
Osaka University Of Pharmaceutical Sciences
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Kaneko Noritsugu
Alfresa Pharma Co.
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Yamatodani Atsushi
Department Of Bioinformatics Graduate School Of Allied Health Sciences Faculty Of Medicine Osaka Uni
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Kurihara T
Osaka University Of Pharmaceutical Sciences
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HARUSAWA Shinya
Osaka University of Pharmaceutical Sciences
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ARAKI Lisa
Osaka University of Pharmaceutical Sciences
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KURIHARA Takushi
Osaka University of Pharmaceutical Sciences
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Yamamoto Ryoko
Department Of Bioinformatics Graduate School Of Allied Health Sciences Faculty Of Medicine Osaka Uni
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Nakao Yumi
Department Of Bioinformatics Graduate School Of Allied Health Sciences Faculty Of Medicine Osaka Uni
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Sakamoto Y
Alfresa Pharma Co.
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Araki L
Osaka University Of Pharmaceutical Sciences
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KAWAMURA Makoto
Osaka University of Pharmaceutical Sciences
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TANIGUCHI Ryusuke
Osaka University of Pharmaceutical Sciences
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YONEYAMA Hiroki
Osaka University of Pharmaceutical Sciences
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SAKAMOTO Yasuhiko
Alfresa Pharma Co.
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HATANO Kouta
Department of Bioinformatics, Graduate School of Allied Health Sciences, Faculty of Medicine, Osaka
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Hatano Kouta
Department Of Bioinformatics Graduate School Of Allied Health Sciences Faculty Of Medicine Osaka Uni
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Fujita Takeshi
Department Of Chemistry Graduate School Of Pure And Applied Sciences University Of Tsukuba
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Fujita Takeshi
Department Of Bioinformatics Graduate School Of Allied Health Sciences Faculty Of Medicine Osaka Uni
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Fujita Takeshi
Department Of Applied Physics Osaka City University
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