On March 15, 2022, Iio, Keita; Saitoh, Tsuyoshi; Ohshita, Ryuichiro; Hino, Tsubasa; Amezawa, Mao; Takayama, Yoshiaki; Nagumo, Yasuyuki; Yamamoto, Naoshi; Kutsumura, Noriki; Irukayama-Tomobe, Yoko; Ishikawa, Yukiko; Tanimura, Ryuji; Yanagisawa, Masashi; Nagase, Hiroshi published an article.Application In Synthesis of 3-Hydroxyphenylacetic acid The title of the article was Discovery of orexin 2 receptor selective and dual orexin receptor agonists based on the tetralin structure: Switching of receptor selectivity by chirality on the tetralin ring. And the article contained the following:
A novel series of 1-amino-tetralin derivatives were designed and synthesized based on the putative binding mode of the naphthalene-type orexin receptor agonist 5 and their agonist activities against orexin receptors were evaluated. The introduction of N-methyl-(3-methoxyphenyl)acetamide unit onto the 1-amino-tetralin skeleton remarkably enhanced the potency of the agonist. The asym. synthesis of 6 revealed that (-)-6 having a (S)-1-amino-tetralin skeleton showed a OX2R selective agonist activity (EC50 = 2.69 nM for OX2R, OX1R/OX2R = 461) yet its enantiomer (R)-(+)-6 showed a potent OX1/2R dual agonist activity (EC50 = 13.5 nM for OX1R, 0.579 nM for OX2R, OX1R/OX2R = 23.3). These results suggested that upward orientation of the amide side chain against the tetralin scaffold (S-configuration) would be selective for OX2R activation, and the downward orientation (R-configuration) would be significant for dual agonist activity. To our best knowledge, there have been no reports thus far that the stereochem. of one carbon center on the agonist structure regulates the orexin receptor selectivity. Our results would provide important information for the development of OX1R selective agonists. The experimental process involved the reaction of 3-Hydroxyphenylacetic acid(cas: 621-37-4).Application In Synthesis of 3-Hydroxyphenylacetic acid
The Article related to orexin 2 receptor agonists chirality structure activity, agonist, diarylsulfonamide, ox1r, ox2r, orexin, orexin receptor, tetraline, Placeholder for records without volume info and other aspects.Application In Synthesis of 3-Hydroxyphenylacetic acid
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