Synthesis and biological evaluation of 4′-[(benzimidazol-1-yl) methyl]biphenyl-2-amides as dual angiotensin II and endothelin A receptor antagonists

MedChemComm
2015.0

Abstract

By introduced a novel fragment [N‐(1H‐tetrazol‐5‐yl)‐amide], a series of 4′‐[(benzimidazol‐1‐yl)methyl] biphenyl‐2‐amides (1a‐1w) was designed, synthesized, and biologically evaluated. 1d, 1k and 1p showed potent antagonistic activities against angiotensin II receptor (AT1) and endothelin A receptor (ETA). The evaluation in spontaneous hypertensive rats indicated that the oral activity of compound 1p was more potent than Irbersartan. Structural biology studies of 1p exhibited that strong interactions were contributed to the AT1 and ETA receptors and the tetrazol‐5‐ylamide could be an important moiety for the binding to the proteins.

Knowledge Graph

Similar Paper

Synthesis and biological evaluation of 4′-[(benzimidazol-1-yl) methyl]biphenyl-2-amides as dual angiotensin II and endothelin A receptor antagonists
MedChemComm 2015.0
Synthesis and biological evaluation of 4′-[(benzimidazole-1-yl)methyl]biphenyl-2-sulfonamide derivatives as dual angiotensin II/endothelin A receptor antagonists
Bioorganic & Medicinal Chemistry 2012.0
Discovery of 4′-[(Imidazol-1-yl)methyl]biphenyl-2-sulfonamides as dual endothelin/Angiotensin II receptor antagonists
Bioorganic & Medicinal Chemistry Letters 2003.0
Design, synthesis and biological activity of 4′-[(benzimidazol-1-yl)methyl]biphenyl-2-sulphonamides as dual angiotensin II and endothelin A receptor antagonists
MedChemComm 2015.0
Synthesis and biological activities of novel nonpeptide angiotensin II receptor antagonists based on benzimidazole derivatives bearing a heterocyclic ring
Bioorganic & Medicinal Chemistry 2008.0
Discovery of N-Isoxazolyl Biphenylsulfonamides as Potent Dual Angiotensin II and Endothelin A Receptor Antagonists
Journal of Medicinal Chemistry 2002.0
Synthesis and Pharmacological Evaluation of New Pyrazolidine-3,5-diones as AT<sub>1</sub> Angiotensin II Receptor Antagonists
Journal of Medicinal Chemistry 2000.0
Imidazolinones as nonpeptide angiotensin II receptor antagonists
Bioorganic &amp; Medicinal Chemistry Letters 1994.0
Development of tetrazole bioisosteres in angiotensin II antagonists
Bioorganic &amp; Medicinal Chemistry Letters 1994.0
Design, synthesis and biological evaluation of 6-substituted aminocarbonyl benzimidazole derivatives as nonpeptidic angiotensin II AT1 receptor antagonists
European Journal of Medicinal Chemistry 2012.0