340321-10-0

Basic information

• Product Name: (4aS,10aR)-10,10-Dimethyl-4-(3-trifluoromethyl-benzoyl)-2,3,4,4a,10,10a-hexahydro-1,9-dioxa-4-aza-phenanthrene-6-carbonitrile
• CAS NO: 340321-10-0
• Molecular Weight: 416.4
• Mol File: 340321-10-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4aS,10aR)-10,10-Dimethyl-4-(3-trifluoromethyl-benzoyl)-2,3,4,4a,10,10a-hexahydro-1,9-dioxa-4-aza-phenanthrene-6-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,10aR)-10,10-Dimethyl-4-(3-trifluoromethyl-benzoyl)-2,3,4,4a,10,10a-hexahydro-1,9-dioxa-4-aza-phenanthrene-6-carbonitrile(340321-10-0)
• EPA Substance Registry System: (4aS,10aR)-10,10-Dimethyl-4-(3-trifluoromethyl-benzoyl)-2,3,4,4a,10,10a-hexahydro-1,9-dioxa-4-aza-phenanthrene-6-carbonitrile(340321-10-0)

Safety Data

• Hazardous Substances Data: 340321-10-0(Hazardous Substances Data)

Upstream product

• 65018-90-8 (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile 
• 340321-16-6 (3R,4S)-3-Hydroxy-4-(2-hydroxy-ethylamino)-2,2-dimethyl-chroman-6-carbonitrile 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 340321-17-7 (4aS,10aR)-10,10-Dimethyl-2,3,4,4a,10,10a-hexahydro-1,9-dioxa-4-aza-phenanthrene-6-carbonitrile 

Relevant articles and documents

N-acyl-1,2,3,4a,5,10b-hexahydro-[1]benzopyrano-[3,4-b][1,4]oxazine-9- carbonitriles as bladder-selective potassium channel openers

Optically active N-acyl-5,5-dimethyl-1,2,3,4a,5,10b-hexahydro-[1]benzopyrano[3,4-b][1,4] oxazine-9-carbonitriles 2-22 were synthesized as rigid analogues of cromakalim. The (4aR,10bR)-N-benzoyl derivative (-)-11 was identified as a bladder-selective KCO (IC50, bladder=8.2 μM, IC50, portal vein=34.5 μM). Among the analogues of 11 with substitution on the benzoyl moiety, the 3-methyl analogue (-)-14 showed highly potent and selective activity at portal vein (IC50, bladder=279 μM, IC50, portal vein=0.54 μM). The 4-bromo analogue (-)-19 (IC50, bladder=2.0 μM, IC50, portal vein=8.1 μM) and the 4-hydroxy analogue (-)-21 (IC50, bladder=3.8 μM, IC50, portal vein=75 μM) showed enhanced activity at the bladder, while maintaining unprecedented bladder selectivity in vitro. The N-benzenesulfonyl analogue (-)-22, a bioisoster of (-)-11, showed similar activity at the bladder with enhanced selectivity (IC50, bladder=11.6 μM, IC50, portal vein=120 μM).