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Recent Trends in Pharmaceutical Analytical Chemistry
Open AccessArticle

Conformational Restriction of Histamine with a Rigid Bicyclo[3.1.0]hexane Scaffold Provided Selective H3 Receptor Ligands

1
Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060–0812, Japan
2
Center for Pharma-Food Research (CPFR), Graduate School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422–8526, Japan
3
Center for Research and Education on Drug Discovery, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060–0812, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Marie Migaud
Molecules 2020, 25(16), 3562; https://doi.org/10.3390/molecules25163562
Received: 16 July 2020 / Revised: 30 July 2020 / Accepted: 4 August 2020 / Published: 5 August 2020
We designed and synthesized conformationally rigid histamine analogues with a bicyclo[3.1.0]hexane scaffold. All the compounds were selectively bound to the H3 receptor subtype over the H4 receptor subtype. Notably, compound 7 showed potent binding affinity and over 100-fold selectivity for the H3 receptors (Ki = 5.6 nM for H3 and 602 nM for H4). These results suggest that the conformationally rigid bicyclo[3.1.0]hexane structure can be a useful scaffold for developing potent ligands selective for the target biomolecules. View Full-Text
Keywords: histamine; H3 receptor; conformational restriction; selective ligands histamine; H3 receptor; conformational restriction; selective ligands
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MDPI and ACS Style

Watanabe, M.; Kobayashi, T.; Ito, Y.; Yamada, S.; Shuto, S. Conformational Restriction of Histamine with a Rigid Bicyclo[3.1.0]hexane Scaffold Provided Selective H3 Receptor Ligands. Molecules 2020, 25, 3562.

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