162269-55-8

Basic information

• Product Name: Methanone, (5-bromo-2-hydroxyphenyl)(3-hydroxy-2-pyridinyl)-
• CAS NO: 162269-55-8
• Molecular Formula: C12H8BrNO3
• Molecular Weight: 294.104
• Mol File: 162269-55-8.mol

Chemical Properties

• CAS DataBase Reference: Methanone, (5-bromo-2-hydroxyphenyl)(3-hydroxy-2-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (5-bromo-2-hydroxyphenyl)(3-hydroxy-2-pyridinyl)-(162269-55-8)
• EPA Substance Registry System: Methanone, (5-bromo-2-hydroxyphenyl)(3-hydroxy-2-pyridinyl)-(162269-55-8)

Safety Data

• Hazardous Substances Data: 162269-55-8(Hazardous Substances Data)

Upstream product

• 21571-52-8 2,4-dibromo-1-(methoxymethoxy)benzene 
• 162271-30-9 2-cyano-3-trimethylsilyloxy pyridine 
• 109-99-9 tetrahydrofuran 
• 116-11-0 2-Methoxypropene 
• 615-58-7 2,4-dibromophenol 

Downstream Products

• 162267-12-1 (Z)-2-[5-bromo-α-(tert-butoxyimino)-2-hydroxybenzyl]-3-hydroxypyridine 
• 162267-73-4 (5-Bromo-4-fluoro-2-hydroxy-phenyl)-(3-hydroxy-pyridin-2-yl)-methanone O-tert-butyl-oxime 

Relevant articles and documents

Pyridine derivatives, their production and use

Pyridine derivatives of the formula STR1 wherein the ring A stands for an optionally further substituted benzene ring; the ring B stands for an optionally substituted pyridine ring; Q stands for hydroxyl group, or OQ 1 or Q 1 wherein Q 1 stands for an optionally substituted aliphatic hydrocarbon group; and n denotes 0 or 1, or their salts, which have potassium.channel opening activity and are useful as therapeutic agents of circulatory diseases such as angina pectoris, hypertension, etc.

Synthesis and biological activity of novel 2-(α- alkoxyimino)benzylpyridine derivatives as K+ channel openers

The search for novel K+ channel openers with a non-benzopyran skeleton, unlike cromakalim, led to the discovery of a new series of (Z)-2-(α- alkoxyimino)benzylpyridine derivatives. Synthesis was achieved by using a (Z)-dominant condensation reaction of henzoylpyridines with O- alkylhydroxylamines, followed by m-chloroperhenzoic acid (m-CPBA) oxidation. The compounds were tested for their vasorelaxant activity in tetraethylammonium chloride (TEA) and BaCl2- and high KCl-induced contraction of rat aorta to identify potential K+ channel openers, and also for their effects on the coronary blood flow (CBF) after intracoronary injection in anesthetized dogs. A large number of the 2-(α- alkoxyimino)benzylpyridines strongly inhibited TEA and BaCl2-induced contraction, had no effect on 80 mM KCl-induced contraction, and increased the CBF to more than 200% of the basal flow at 10-30μg/dog. In particular, (Z)-2-[5-bromo-α-(tert-butoxyimino)-4-fluoro-2-hydroxybenzyl]-3- hydroxypyridine 1-oxide (7d) showed highly potent vasorelaxant activity (EC50=0.28μM) comparable to that of levcromakalim (EC50=0.17 μM), and gave a significantly longer-lasting increase (T ( 1/4 ) = 30 min) in the CBF compared to levcromakalim, nicorandil, nitroglycerin, or diltiazem (T( 1/4 )=5.2, 0.9, 0.4, and 2.2 min, respectively). It also exhibited a stable and long-lasting hypotensive effect (over 7h) upon oral administration of 1 mg/kg in spontaneously hypertensive rats (SHRs).