69552-46-1

Usage

Uses

Used in Pharmaceutical Industry:
Carbacyclin is used as an antiplatelet agent for its ability to inhibit ex vivo platelet aggregation in rabbits and dogs, with an effect that persists for about 10 minutes after the termination of the infusion. It exhibits 10% of the molar potency of PGI2 in inhibiting platelet aggregation, and its ED50 for in vitro inhibition of ADP-induced platelet aggregation in human PRP is 47 nM.
Used in Regenerative Medicine:
Carbacyclin is used as a promoter of terminal differentiation of preadipose cells into adipose cells, enhancing the expression of angiotensinogen and adipose fatty acid binding protein with an EC50 of about 0.5 μM.
Used in Oncology:
Carbacyclin is used in the treatment of high-risk acute lymphoblastic leukemia, where it acts to potentiate the activity of anti-cancer therapeutics, potentially improving patient outcomes and response to treatment.

InChI:InChI=1/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1

Upstream product

• 73996-33-5 3α-hydroxy-7-oxo-2β-hydroxymethylbicyclo<3.3.0>octane 3-tetrahydropyranyl ether 
• 71845-98-2 (5E)-6a-carbaprostaglandin I₂ bis(tetrahydropyranyl) ether 
• 69552-46-1 (+/-)-6,9a-methanoprostaglandin I2 
• 41138-68-5 (S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene 
• 94516-91-3 [(1R,2S,3R)-5-Methylene-3-(tetrahydro-pyran-2-yloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopentyl]-acetaldehyde 
• 35563-52-1 1-tributylphosphoranylidene-2-heptanone 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 70870-94-9 (1S,2R,3R,5R)-2-ethoxycarbonyl-7,7-ethylenedioxy-3-hydroxy-bicyclo<3.3.0>octane 
• 74163-85-2 methyl 3α-hydroxy-5-oxo-2β-(benzyloxymethyl)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether 
• 74080-58-3 methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether 
• 73996-31-3 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (α-isomer) 
• 71846-05-4 Methyl (1S,5S,6R,7R)-7-Hydroxy-6-(3-oxo-E-1-octenyl)bicyclo<3.3.0>octane-E-Δ^3.δ-pentanoate 
• 53539-02-9 methyl 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetate 
• 37517-42-3 7-tetrahydropyranyloxy-6-<(1E)-3-tetrahydropyranyloxy-1-octenyl>-2-oxabicyclo<3.3.0>octan-2-one 

Downstream Products

• 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.

Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues

A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized ω-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF2α, and the formal syntheses of 15-deoxy-TIC and PGJ2.

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.

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 CARBACYCLIN USING RHODIUM(I) COMPLEX

The key intermediate (11) for the synthesis of carbacyclin (1) was synthesized by the application of a new method for stereoselective five-membered ring formation using Wilkinson complex. KEYWORDS --- carbacyclin; Wilkinson complex; cyclization; five-memb