Publication

5a-carba-beta-D-, 5a-carba-beta-L- and 5-thio-beta-L-xylopyranosides as new orally active venous antithrombotic agents

Pierre Vogel
1998
Journal Articles

Abstract

Mitsunobu displacement of (-)-(1S,4R,5S,6S) -4,5,6-tris{[(tert-butyl)dimethylsilyl] oxy}cyclohex-2-en-1-ol ((-)-12; a (-)-conduritol-F derivative) with 4-ethyl-7-hydroxy-2H-1-benzopyran-2-one (16) provided a 5a-carba-beta-D-pyranoside (+)-17 that was converted into (+)-4-ethyl-7-[(1'R,4'R,5'S,6'R)-4',5',6'-trihydroxycyclohex-2'-en-1'-yl oxy]-2H-1-benzopyran-2-one ((+)-5) and (+)-4-ethyl-7-[(1'R,2'R,3'S,4'R) -2',3',4'-trihydroxycyclohexyloxy]-2H-1-benzopyran-2-one ((+)-6). The 5a-carba-beta-D-xyloside (+)-6 was an orally active antithrombotic agent in the rat (venous Wessler's test),but less active than racemic carba-beta-xylosides (+/-)-5 and (+/-)-6. The 5a-carba-beta-L-xyloside (-)-6 was derived from the enantiomer (+)-12 and found to be at least 4 times as active as (+)-6. (+)-4-Cyanophenyl 5-thio-beta-L-xylopyranoside ((+)-3) was synthesized from L-xylose and found to maintain ca. 50% of the antithrombotic activity of its D-enanriomer. Compounds (+/-)-5, (+/-)-6, and (-)-6 are in vitro substrates for galactosyltransferase 1.

Official source

https://infoscience.epfl.ch/entities/publication/f94bd015-2790-4e00-ba4e-9e672628cc20

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Pierre Vogel
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f94bd015-2790-4e00-ba4e-9e672628cc20

About this result

Related concepts (6)

Coagulation

Coagulation, also known as clotting, is the process by which blood changes from a liquid to a gel, forming a blood clot. It potentially results in hemostasis, the cessation of blood loss from a damaged vessel, followed by repair. The mechanism of coagulation involves activation, adhesion and aggregation of platelets, as well as deposition and maturation of fibrin. Coagulation begins almost instantly after an injury to the endothelium lining a blood vessel.

Warfarin

Warfarin is an anticoagulant used as a medication under several brand names including Coumadin. While the drug is described as a "blood thinner", it does not reduce viscosity but inhibits coagulation, and is commonly used to prevent blood clots in the circulatory system such as deep vein thrombosis and pulmonary embolism, and to protect against stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Less commonly, it is used following ST-segment elevation myocardial infarction and orthopedic surgery.

Low-molecular-weight heparin

Low-molecular-weight heparin (LMWH) is a class of anticoagulant medications. They are used in the prevention of blood clots and treatment of venous thromboembolism (deep vein thrombosis and pulmonary embolism) and in the treatment of myocardial infarction. Heparin is a naturally occurring polysaccharide that inhibits coagulation, the process that leads to thrombosis. Natural heparin consists of molecular chains of varying lengths, or molecular weights.