Literature DB >> 28355078

Discovery of Novel Indazole Derivatives as Orally Available β3-Adrenergic Receptor Agonists Lacking Off-Target-Based Cardiovascular Side Effects.

Yasuhiro Wada1, Seiji Nakano1, Akifumi Morimoto1, Ken-Ichi Kasahara1, Takahiko Hayashi1, Yoshio Takada1, Hiroko Suzuki1, Michiko Niwa-Sakai1, Shigeki Ohashi1, Mutsuhiro Mori1, Takatsugu Hirokawa2,3, Satoshi Shuto.   

Abstract

We previously discovered that indazole derivative 8 was a highly selective β3-adrenergic receptor (β3-AR) agonist, but it appeared to be metabolically unstable. To improve metabolic stability, further optimization of this scaffold was carried out. We focused on the sulfonamide moiety of this scaffold, which resulted in the discovery of compound 15 as a highly potent β3-AR agonist (EC50 = 18 nM) being inactive to β1-, β2-, and α1A-AR (β1/β3, β2/β3, and α1A/β3 > 556-fold). Compound 15 showed dose-dependent β3-AR-mediated responses in marmoset urinary bladder smooth muscle, had a desirable metabolic stability and pharmacokinetic profile (Cmax and AUC), and did not obviously affect heart rate or mean blood pressure when administered intravenously (3 mg/kg) to anesthetized rats. Thus, compound 15 is a highly potent, selective, and orally available β3-AR agonist, which may serve as a candidate drug for the treatment of overactive bladder without off-target-based cardiovascular side effects.

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Year:  2017        PMID: 28355078     DOI: 10.1021/acs.jmedchem.6b01197

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  4 in total

1.  Association between Inhaled β2-agonists Initiation and Risk of Major Adverse Cardiovascular Events: A Population-based Nested Case-Control Study.

Authors:  Joseph Emil Amegadzie; John-Michael Gamble; Jamie Farrell; Zhiwei Gao
Journal:  Int J Chron Obstruct Pulmon Dis       Date:  2022-05-20

Review 2.  Everything You Always Wanted to Know about β3-AR * (* But Were Afraid to Ask).

Authors:  Giorgia Schena; Michael J Caplan
Journal:  Cells       Date:  2019-04-16       Impact factor: 6.600

Review 3.  Cyclobutanes in Small-Molecule Drug Candidates.

Authors:  Marnix R van der Kolk; Mathilde A C H Janssen; Floris P J T Rutjes; Daniel Blanco-Ania
Journal:  ChemMedChem       Date:  2022-03-29       Impact factor: 3.540

Review 4.  Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives.

Authors:  Shu-Guang Zhang; Chao-Gen Liang; Wei-Hua Zhang
Journal:  Molecules       Date:  2018-10-26       Impact factor: 4.411

  4 in total

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