273213-64-2

Basic information

• Product Name: (3S,4R)-3-Hydroxy-4-[(1S,6R)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile
• CAS NO: 273213-64-2
• Molecular Weight: 447.491
• Mol File: 273213-64-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-Hydroxy-4-[(1S,6R)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-Hydroxy-4-[(1S,6R)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile(273213-64-2)
• EPA Substance Registry System: (3S,4R)-3-Hydroxy-4-[(1S,6R)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile(273213-64-2)

Safety Data

• Hazardous Substances Data: 273213-64-2(Hazardous Substances Data)

Upstream product

• 140-69-2 4-methoxybenzylhydrazine 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 65018-90-8 6-cyano-2,2-dimethylchromene-3,4-epoxide 
• 154186-47-7 (+/-)-3-(4-methoxybenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione 

Relevant articles and documents

Novel potassium channel opener prodrugs with a slow onset and prolonged duration of action

(-)-(3S,4R,1'R,6'S)-4-(4-Benzyl-5-oxo-3,4-diazabicyclo[4.1.0.]hept-2-en- 2-yloxy)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and its derivatives with a modified benzyl group were synthesized with the objective of discovering novel ATP-sensitive potassium channel openers (PCOs) with a slow onset of action and a reduced tendency to induce tachycardia. Among the compounds synthesized, 4-(2-chlorobenzyl) derivative 5bB had potent hypotensive activity in spontaneously hypertensive rats (SHRs). In addition, compound 5bB showed the desired pharmacological profile with a slow onset and long duration of action and induction of only mild tachycardia. Compound 5bB was found to be quantitatively metabolized in rats to give active des-2- chlorobenzyl derivative 6B. These results suggest that the incorporation of an N-benzyl group is a useful method for the preparation of prodrugs, the function of which is to delay the onset and prolong the duration of action of the active substance.