69609-77-4

Usage

Uses

Used in Pharmaceutical Industry:
(5Z)-6A-CARBAPROSTAGLANDIN I2 is used as a therapeutic agent for cardiovascular diseases such as hypertension and thrombosis. Its vasodilatory and platelet aggregation inhibition properties contribute to its effectiveness in managing these conditions.
Used in Anti-Inflammatory Applications:
(5Z)-6A-CARBAPROSTAGLANDIN I2 is used as an anti-inflammatory agent for conditions involving excessive inflammation, such as rheumatoid arthritis and inflammatory bowel disease. Its ability to regulate inflammation can provide relief and improve the quality of life for patients suffering from these conditions.
Used in Research and Development:
Due to its synthetic nature, (5Z)-6A-CARBAPROSTAGLANDIN I2 is used as a research tool for studying the pharmacokinetic and pharmacodynamic properties of prostaglandin analogs. This can lead to the development of improved therapeutic agents with better efficacy and fewer side effects.

Upstream product

• 71845-98-2 (5E)-6a-carbaprostaglandin I₂ bis(tetrahydropyranyl) ether 
• 71884-07-6 (5Z)-6α-carbaprostaglandin I₂ methyl ester 
• 102491-13-4 (+)-(5Z)-9(O)-methanoprostacyclin methyl ester 11,15-diacetate 
• 69552-48-3 methyl (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylate 
• 35563-52-1 1-tributylphosphoranylidene-2-heptanone 
• 69552-54-1 (-)-(1S,2R,3R,5R)-2-(3(S)-hydroxyoct-1(E)-enyl)-7-oxobicyclo<3.3.0>octan-3-ol 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 70871-22-6 (-)-(1S,2S,3R,5R)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-methanol 
• 70871-21-5 methyl (+)-(1S,2R,3R,5R)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylate 
• 70897-06-2 (+)-(5E,Z)-9(O)-methanoprostacyclin methyl ester 
• 71753-74-7 (+)-(1S,2R,3R,5R)-2-(3-oxooct-1(E)-enyl)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane 
• 74035-19-1 5-[(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid 
• 102917-72-6 (+)-(1S,2R,3R,5R)-3-hydroxy-7,7-ethylenedioxybicyclo<3.3.0>octane-2-carboxylic acid l(-)-α-methylbenzylamine salt 
• 71753-75-8 (+)-(1S,2R,3R,5R)-2-(3-hydroxyoct-1(E)-enyl)-3-(tetrahydropyran-2-yl)oxy-7,7-ethylenedioxybicyclo<3.3.0>octane 

Downstream Products

• 69552-46-1 (5E)-carba-PGI2 
• 102491-28-1 (-)-ent-9(O)-methanoprostacyclin 

Relevant academic research and scientific papers

Facile synthesis of 6a-carbaprostaglandin I2

The optically active 6a-carbaprostaglandin I2 (2), a stable mimic of natural prostacyclin (1), was synthesized from the lactone 4 or the hydroxy acid 5, which were general synthetic intermediates for natural prostaglandins.

PROSTANOIDS. LII. (+/-)-7,7-DICHLORO-4β-TRIMETHYLSILYLBICYCLOHEPT-3-EN-6-ONE IN THE SYNTHESIS OF PROSTANOIDS. RACEMIC CARBACYCLIN

The products from the Prins reaction of formaldehyde and (+/-)-7,7-dichloro-4β-trimethylsilylbicyclohept-3-en-6-one were isolated and characterized.The optimum conditions were found for the production of the isomeric 2β-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and 2β-acetoxymethyl-3α-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and also (1R,2S,5R,6S,10R)-3,3-dichloro-4-oxo-10-hydroxy(acetoxy)-8-oxatricyclo2,5>undecanes, suitable for the subsequent synthesis of modified prostanoids.An effective scheme for the synthesis of (+/-)-carbacyclin was worked out on the basis of the monoacetates of a series of bicycloheptenones through the corresponding 2β-acetoxymethyl-3α-acetoxybicyclooctan-7-ones.

Novel prostacyclin derivatives and a process for the preparation thereof

Compounds of the formula STR1 wherein R1 is (a) hydrogen, (b) C1-10 alkyl, (c) C1-10 alkyl substituted by halogen; C1-4 alkoxy; C6-10 aryl; C6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C1-4 alkoxy group; di-C1-4 -alkylamino; or tri-C1-4 -alkylammonium, (d) C4-10 cycloalkyl, (e) C4-10 cycloalkyl substituted by C1-4 alkyl, (f) C6-10 aryl, (g) C6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S; A is --CH2 --CH2 --, trans--CH=CH-- or --C C--; W is hydroxymethylene, RO-methylene, CH3 or CH3, STR2 wherein OH or OR is in the α- or β-position and R is an in vivo hydrolyzable and physiologically acceptable ether or acyl group which is conventional for modifying OH groups in prostaglandins; D and E together are a direct bond, or D is C1-10 alkylene, C1-10 alkenylene or C1-10 alkynylene or one of these groups substituted by fluorine, and E is oxygen, --C C-- or a direct bond; R2 is (a) a C1-10 hydrocarbon aliphatic radical, (b) a C6-10 hydrocarbon aliphatic radical substituted by C6-10 aryl or by C6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C1-4 alkoxy group; (c) C4-10 cycloalkyl, (d) C4-10 cycloalkyl substituted by C1-4 alkyl, (e) C6-10 aryl, (f) C6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C1-4 alkoxy group; or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S; and R3 is OH or OR; and, when R1 is hydrogen, the salts thereof with physiologically compatible bases, are effective as antihypertensive, bronchiodilators, thrombocyte aggregation inhibitors, inter alia.

A NEW SYNTHESIS OF (+)-6a-CARBAPROSTAGLANDIN I2 EMPLOYING YEAST REDUCTION OF A β-KETO ESTER DERIVED FROM cis-BICYCLOOCTANE-3,7-DIONE AS THE KEY-STEP

(+)-6a-carbaprostaglandin I2 (carbacyclin), a stable mimic of prostaglandin I2 (prostacyclin), was synthesized by utilizing the kinetic resolution of (+/-)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclooctan-3-one in the course of its yeast reduction as

Synthesis of Stable Prostacyclin Analogues from 2,3-Disubstituted Bicycloheptan-6-ones

A short synthesis of 9-deoxy-6-9α-methanoepoxy-Δ5-prostaglandin F1 (14) from bicycloheptan-6-one (3) is described.The ketone (3) can be converted by known methods into the vinyl ether (8).In the presence of mercury(II) acetate at 100 deg C, the 5-hydroxyalk-1-enyl methyl ether (8) undergoes a novel intramolecular vinyl transetherification reaction to give the Δ2-dihydropyran (9).Hydroboration-oxidation of the dihydropyran (9) furnished selectively the tetrahydropyran-3-ol (10).Subsequent elaboration via oxidation, Wittig olefination, and deprotection afforded 9-deoxy-6,9α-methanoepoxy-Δ5-prostaglandin F1 (14).The protected bicycloheptan-6-one (16) underwent a ring expansion with diazomethane, producing a 1:1 mixture of the two homologated ketones (17) and (18).Wittig olefination and deprotection of these ketones provided 15-epi-9-deoxy-6,9α-methano-Δ5-prostaglandin F1 (19) and its structural isomer (20).The two bicycloheptan-6-ones (3) and (4) also led directly to a series of 9-deoxy-6,9α-cycloprostaglandins F1 via Wittig reactions.

Process for the production of caracyclin intermediates

A process for preparing a 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester of the formula STR1 wherein R1 is alkyl of 1-6 carbon atoms or phenalkyl of 7-10 carbon atoms and R2 is hydrogen, alkyl or 1-6 carbon atoms, phen