Synthesis and pharmacological activity of O-(5-isoxazolyl)-L-serine.
A novel isoxazole derivative, O-(5-isoxazolyl)-L-serine (OIS, 1), was synthesized by a Mitsunobu reaction of isoxazolin-5-one (4) with N-Boc-L-serine tert-butyl ester (5) and subsequent deprotection of the coupling product. Its structure was elucidated by spectroscopic analyses. The pharmacological activity of 1 was also examined with cloned glutamate receptors and transporters using a Xenopus oocyte-expressing system showing substrate activity on an excitatory amino acid carrier 1 (EAAC 1) as a glutamate transporter.
Ikegami
F
F
Faculty of Pharmaceutical Sciences, Chiba University, Japan.
Yamamoto
A
A
Sekine
T
T
Ishikawa
T
T
Kusamae-Eguchi
K
K
Kusama
T
T
Watanabe
K
K
D018528:ATP-Binding Cassette Transporters / Q000187:drug effects; D027322:Amino Acid Transport System X-AG; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D018691:Excitatory Amino Acid Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D007536:Isomerism; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D018532:Pisum sativum / Q000737:chemistry; D017470:Receptors, Glutamate / Q000187:drug effects; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014981:Xenopus
D018528:ATP-Binding Cassette Transporters; D027322:Amino Acid Transport System X-AG; D000596:Amino Acids; D018691:Excitatory Amino Acid Antagonists; D007202:Indicators and Reagents; D007555:Isoxazoles; C406467:O-(5-isoxazolyl)serine; D017470:Receptors, Glutamate; D012694:Serine