1221235-53-5

Basic information

• Product Name: cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone
• Synonyms: cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone
• CAS NO: 1221235-53-5
• Molecular Weight: 194.206
• Mol File: 1221235-53-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone(1221235-53-5)
• EPA Substance Registry System: cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone(1221235-53-5)

Safety Data

• Hazardous Substances Data: 1221235-53-5(Hazardous Substances Data)

Upstream product

• 4399-47-7 Bromocyclobutane 
• 175968-15-7 4-((tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile 
• 82380-18-5 2-fluoro-4-hydroxybenzonitrile 
• 13384-48-0 cyclobutylmagnesium bromide 

Downstream Products

• 1221235-54-6 1-benzyl-3-cyclobutyl-1H-indazol-6-ol 
• 1221235-56-8 6-((tert-butyldiphenylsilyl)oxy)-3-cyclobutyl-1H-indazole 
• 1221235-57-9 tert-butyl 6-((tert-butyldiphenylsilyl)oxy)-3-cyclobutyl-1H-indazole-1-carboxylate 
• 1221235-59-1 (R)-tert-butyl 6-(2-(tert-butoxycarbonyl(2-(3-(N-(tert-butoxycarbonyl)methylsulfonamide)phenyl)-2-(triethylsilyloxy)ethyl)amino)ethoxy)-3-cyclobutylindazole-1-carboxylate 

Relevant articles and documents

Discovery of Novel Indazole Derivatives as Highly Potent and Selective Human β3-Adrenergic Receptor Agonists with the Possibility of Having No Cardiovascular Side Effects

Novel indazole derivatives were prepared and evaluated for their biological activity and cardiovascular safety profile as human β3-adrenergic receptor (AR) agonists. Although the initial hit compound 5 exhibited significant β3-AR agonistic activity (EC50 = 21 nM), it also exhibited agonistic activity at the α1A-AR (EC50 = 219 nM, selectivity: α1A/β3 = 10-fold). The major metabolite of 5, which was an oxidative product at the indazole 3-methyl moiety, gave a clue to a strategy for improvement of the selectivity for β3-AR agonistic activity versus α1A-AR agonistic activity. Thus, modification of the 3-substituent of the indazole moiety effectively improved the selectivity to develop compound 11 with potent β3-AR agonistic activity (EC50 = 13 nM) and high selectivity (α1A/β3 = >769-fold). Compound 11 was also inactive toward β1 and β2-ARs and showed dose dependent β3-AR mediated relaxation of marmoset urinary bladder smooth muscle, while it did not obviously affect heart rate or blood pressure (iv, 3 mg/kg) in anesthetized rats.

INDAZOLE DERIVATIVES

Compounds represented by the Formula (A-1) and the Formula (1) or salt thereof are provided. The compounds represented by the Formula (A-1) and the Formula (1) or salt thereof have a β3 adrenergic receptor agonist activity, and therefore are useful as an agent for the prevention and treatment of diabetes, obesity, hyperlipidemia, depression, biliary stone, a disorder derived from hyperactivity of biliary tract, a disorder derived from hyperactivity of digestive tract, interstitial cystitis, overactive bladder, urinary incontinence or a disorder derived from decreased tear secretion, etc.