212311-08-5

Basic information

• Product Name: 9-Chloro-9,15-dideoxy-16(S)-(1-ethylcyclobutyl)-16-hydroxy-17,18,19,20-tetranorprostaglandin F2beta
• Synonyms: ONO-8815
• CAS NO: 212311-08-5
• Molecular Formula: C₂₂H₃₅ClO₄
• Molecular Weight: 398.97485
• Mol File: 212311-08-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 9-Chloro-9,15-dideoxy-16(S)-(1-ethylcyclobutyl)-16-hydroxy-17,18,19,20-tetranorprostaglandin F2beta(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Chloro-9,15-dideoxy-16(S)-(1-ethylcyclobutyl)-16-hydroxy-17,18,19,20-tetranorprostaglandin F2beta(212311-08-5)
• EPA Substance Registry System: 9-Chloro-9,15-dideoxy-16(S)-(1-ethylcyclobutyl)-16-hydroxy-17,18,19,20-tetranorprostaglandin F2beta(212311-08-5)

Safety Data

• Hazardous Substances Data: 212311-08-5(Hazardous Substances Data)

Upstream product

• 255721-54-1 (2R,3R)-2,3-epoxy-4,4-trimethylene-1-hexanol 
• 212311-42-7 (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester 
• 433231-74-4 (Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 
• 212311-43-8 methyl (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((E)-4-(tert-butyldimethylsilyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl)-5-hydroxy-cyclopentyl)-hept-5-enoate 
• 433220-16-7 methyl (Z)-7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-((E)-4-(tert-butyldimethylsilyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl)-5-oxo-cyclopentyl)-hept-5-enoate 
• 433231-72-2 (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 
• 443907-71-9 (Z)-7-[(1R,2R,3R,5R)-2-[(S)-1-Acetoxy-2-benzenesulfonyl-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-butyl]-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 433922-23-7 (Z)-7-[(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 255721-46-1 (5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester 
• 261772-21-8 (5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester 
• 255721-59-6 (3R)-1-benzenesulfonyl-3-(tetrahydro-2H-pyran-2-yl)oxy-4,4-trimethylenehexane 
• 433922-22-6 Benzoic acid (S)-3-benzenesulfonyl-1-(1-ethyl-cyclobutyl)-propyl ester 
• 255721-56-3 (3S)-4,4-Propano-1-tosyloxy-3-hexanol 
• 255721-58-5 (3R)-1-benzenesulfonyl-4,4-(trimethylene)hexane-3-ol 

Relevant articles and documents

Synthesis of a highly selective EP2-receptor agonist

A practical method for the synthesis of the prostanoid EP2-receptor agonist 1 was developed. This method includes magnesium-mediated Julia olefination of aldehyde 2 with the optically active sulfone 3, which was prepared from allylic alcohol 4 using the Sharpless asymmetric epoxidation procedure.

Development of a highly selective EP2-receptor agonist. Part 2: Identification of 16-Hydroxy-17,17-trimethylene 9β-chloro PGF derivatives

Further chemical modification of 1a and 2 was undertaken to identify a more chemically stable selective EP2-receptor agonist for development as a clinical candidate. 9β-Chloro PG analogues 4a e and 5a, c e were found to be potent and selective EP2-receptor agonists. Among them, the compound 4aLy, which is a chemically stabilized lysine salt of 4a, exhibited an excellent profile both in biological activities and physicochemical properties. The agonist 4aLy was found to suppress uterine motility in anesthetized pregnant rats, while PGE2 stimulated uterine motility. Structure activity relationships (SARs) are discussed. Copyright