166374-48-7

Basic information

• Product Name: 8-[(1S,2R,4S,5S,6R)-3-oxatricyclo[3.2.1.0~2,4~]oct-6-yl]-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione
• CAS NO: 166374-48-7
• Molecular Formula: C₁₈H₂₄N₄O₃
• Molecular Weight: 344.4082
• Mol File: 166374-48-7.mol

Chemical Properties

• Boiling Point: 596.1°C at 760 mmHg
• Flash Point: 314.3°C
• Density: 1.32g/cm³
• Vapor Pressure: 3.57E-14mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 8-[(1S,2R,4S,5S,6R)-3-oxatricyclo[3.2.1.0~2,4~]oct-6-yl]-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-[(1S,2R,4S,5S,6R)-3-oxatricyclo[3.2.1.0~2,4~]oct-6-yl]-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione(166374-48-7)
• EPA Substance Registry System: 8-[(1S,2R,4S,5S,6R)-3-oxatricyclo[3.2.1.0~2,4~]oct-6-yl]-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione(166374-48-7)

Safety Data

• Hazardous Substances Data: 166374-48-7(Hazardous Substances Data)

Upstream product

• 190316-04-2 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 
• 102096-61-7 (R)-pantolactone (1S,2S,4S)-bicyclo<2.2.1>hept-5-ene-2-carboxylate 
• 638132-95-3 6-amino-1,3-dipropyl-5-{[(1S,2S)-5-norbornen-2-yl-carbonyl]-(o-nitrobenzyl)}aminouracil 
• 638132-96-4 1,3-dipropyl-7-o-nitrobenzyl-8-[(1S,2S)-5-norbornen-2-yl]xanthine 
• 244622-23-9 (-)-(1S,2S)-5-norbornene-2-carboxylic acid chloride 
• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 638132-97-5 1,3-dipropyl-7-o-nitrobenzyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine 
• 190316-05-3 8-<(1S,2S)-5-Norbornen-2-yl>-1,3-dipropylxanthine 
• 190316-02-0 (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 
• 214920-46-4 5-norbornene-endo-2-carbonyl chloride 
• 126983-35-5 (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester 
• 58001-99-3 5-norbornene-2-carboxylic acid 
• 190316-03-1 1,3-dipropyl-8-((1R,2R)-5-norbornen-2-yl)xanthine 

Relevant articles and documents

Methods of treating pulmonary disease

Methods useful for reducing pulmonary vasoconstriction or improving pulmonary hemodynamics in a patient are disclosed. More particularly, this invention relates to administering A1 adenosine receptor antagonists to reduce pulmonary vasoconstriction and improve pulmonary hemodynamics.

Synthesis of an o-nitrobenzyl attached A1 adenosine receptor antagonist, a prodrug approach

The o-nitrobenzyl group, possessing distinct advantage of being photolabile under mild conditions, was successfully connected to 8-(5,6-epoxynorbornan-2-yl)-1,3-dipropylxanthine (5), a high specific A1 adenosine receptor antagonist. The resulting compound 4 would have potential use as a prodrug.

Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

The individual enantiomers 8 and 12 of the potent and highly selective racemic A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6- epoxynorbornyl)]xanthine (ENX, 4) were synthesized utilizing asymmetric Diels-Alder cycloadditions for the construction of the norbornane moieties. The absolute configuration of 12 was determined by X-ray crystallography of the 4-bromobenzoate 14, which was derived from the bridged secondary alcohol 13. The latter was obtained from 12 by an acid-catalyzed intramolecular rearrangement. The binding affinities of the enantiomers 8 and 12 and the racemate 4 at guinea pig, rat, and cloned human A1- and A(2a)-adenosine receptor subtypes were determined. The S-enantiomer 12 (CVT-124) appears to be one of the more potent and clearly the most A1-selective antagonist reported to date, with K(i) values of 0.67 and 0.45 nM, respectively, at the rat and cloned human A1-receptors and with 1800-fold (rat) and 2400-fold (human) subtype selectivity. Both enantiomers, administered intravenously to saline-loaded rats, induced diuresis via antagonism of renal A1-adenosine receptors.