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

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

A practical synthesis and biological evaluation of 9-halogenated PGF analogues.

A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine.

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

Cycloalkyl-prostaglandin E2 derivatives

A omega -cycloalkyl-prostaglandin E2 derivatives of the formula (I) wherein R is carboxy or hydroxymethyl; R1 is oxo, methylene or halogen atom; R2 is H, OH or C1-4 alkoxy; R3 is H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkyl, C2-8 alkenyl or C2-8 alkynyl substituted by 1-3 of substituent selected from halogen atom, C1-4 alkoxy, C3-7 cycloalkyl, phenyl, or phenyl substituted by 1-3 of substituent selected from halogen atom, C1-4 alkyl, C1-4 alkoxy, nitro, trifluoromethyl; n is 0-4; and non-toxic salt thereof, prodrug thereof and cyclodextrin clathrate thereof can strongly bind on EP2 subtype receptor. Therefore, they are useful for prevention and/or treatment of immune disease (autoimmune disease, organ transplantation, etc.), asthma, abnormal bone formation, neuron cell death, liver damage, abortion, premature birth or retina neuropathy of glaucoma etc.