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Beraprost

Beraprost structure

Beraprost 

structure
  • CAS No:

    88430-50-6

  • Formula:

    C24H30O5

  • Chemical Name:

    Beraprost

  • Synonyms:

    1H-Cyclopenta[b]benzofuran-5-butanoic acid,2,3,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyl-1-octen-6-yn-1-yl)-;1H-Cyclopenta[b]benzofuran-5-butanoic acid,2,3,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyl-1-octen-6-ynyl)-;2,3,3a,8b-Tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyl-1-octen-6-yn-1-yl)-1H-cyclopenta[b]benzofuran-5-butanoic acid;Beraprost;ML 1229;MDL 201229

  • Categories:

    Biochemical Engineering  >  Inflammation Mediators

Beraprost Basic Attributes

398.49

398.49

1312995-182-4

DTXSID7049136

B - Blood and blood forming organs

Characteristics

86.99000

2.87

1.3±0.1 g/cm3

572.1±50.0 °C at 760 mmHg

193.1±23.6 °C

1.625

Drug Information

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

4-(1,2,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyloct-6-yne-1-enyl)-5-cyclopenta(b)benzofuranyl)butyrate

Beraprost Use and Manufacturing

Methods of Manufacturing

Alcohol (I) is oxidatively dehydrogenated with dimethyl sulfoxide-dicyclohexylcarbodiimide (DCC) in anhydrous benzene and pyridine to give aldehyde (Ⅱ); then under the protection of argon, immediately add the phosphide (Ⅲ) ) And sodium hydride in ethylene glycol dimethyl ether, condensation to obtain compound (IV), a yield of 80%. (IV) Reduction with lithium aluminum hydride to obtain 44% of compound (V), and finally hydrolysis to obtain beraprost.

Uses

Platelet aggregation inhibitor; stable analog of Prostacyclin. Antithrombotic; vasodilator (peripheral).

Computed Properties

Molecular Weight:398.5
XLogP3:3.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:398.20932405
Monoisotopic Mass:398.20932405
Topological Polar Surface Area:87
Heavy Atom Count:29
Complexity:659
Undefined Atom Stereocenter Count:6
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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