435-97-2 Usage
Description
Phenprocoumon, also known as Liquamar, is a synthetic oral anti-coagulant belonging to the class of 4-hydroxycoumarins. It is a white solid substance with a 1-phenylpropyl group substitution at position 3. Phenprocoumon is primarily used to prevent blood clot formation and is a promising pharmaceutical candidate for various medical applications.
Uses
Used in Pharmaceutical Industry:
Phenprocoumon is used as an oral anti-coagulant for the prevention and treatment of blood clots. It works by inhibiting the synthesis of vitamin K-dependent clotting factors, thereby reducing the risk of thromboembolic events such as deep vein thrombosis, pulmonary embolism, and stroke. Additionally, it is used in the management of atrial fibrillation and in patients with prosthetic heart valves.
Used in Cardiovascular Applications:
Phenprocoumon is used as a therapeutic agent in the treatment of cardiovascular conditions where there is an increased risk of blood clot formation. It helps in maintaining a balance between the clotting and bleeding processes, ensuring that the blood remains fluid and preventing the formation of harmful blood clots.
Used in Atrial Fibrillation Management:
Phenprocoumon is used as an anti-coagulant in the management of atrial fibrillation, a common heart rhythm disorder. By reducing the risk of blood clot formation, it helps in preventing stroke and other thromboembolic complications associated with this condition.
Used in Prosthetic Heart Valve Patients:
Phenprocoumon is used as an anti-coagulant in patients with prosthetic heart valves to prevent the formation of blood clots around the artificial valve, which can lead to valve dysfunction or embolic events.
Originator
Liquamar ,Organon ,US,1958
Manufacturing Process
8.3 parts by weight of powdered sodium in 300 parts by volume of benzene, 100 parts by weight of diethyl (1'-phenylpropyl)-malonate and 72 parts by weight of acetylsalicylic acid chloride are reacted together to form diethyl 1(o-acetoxybenzoy1)-1-(1'-phenylpropyl)malonate, which boils at 195°198°C/0.03 mm Hg.10.3 parts of weight of diethyl 1-(o-acetoxybenzoyl)-1-(1'-phenylpropyl)malonate are dissolved in 60 parts by volume of absolute ether and to this solution are added portion. wise at 10°C, while stirring, 2.6 parts by weight of sodium methylate. The reaction mixture is stirred for 4 hours, whereupon it is poured into ice water. The ether solution is washed neutral with ice water. After having distilled off the ether, a thick oil consisting of 3-carbethoxy-3-(1'phenylpropyl)-4-oxo-dihydrocoumarinis obtained. This compound crystallized in butyl oxide and has a MP of 108°-109°C.The 3-carbethoxy-3-(1'-phenylpropyl)-4-oxo-dihydrocoumarinmay be hydrolyzed and decarboxylated as follows. The crude product is heated to 85°C for 1/2 hour with 100 parts by volume of 5% aqueous sodium hydroxide, while agitating or stirring. To remove traces of undissolved oil, the cooled solution is treated with 1 part by weight of charcoal, whereupon it is filtrated and acidified to Congo reaction with dilute sulfuric acid. The 3-(1'phenylpropyl)-4-hydroxycoumarin formed is separated off and recrystallized in 80% ethanol, whereupon it melts at 178°-179°C according to US Patent 2,701,804.
Therapeutic Function
Anticoagulant
Synthesis
Phenprocoumon, 3-(α-ethylbenzyl)-4-hydroxycoumarin (24.1.14), is
synthesized by acylating sodium salts of diethyl ester (1-phenylpropyl)butyric acid with
acetylsalicylic acid chloride, which forms the compound 24.1.12, which upon reaction
with sodium ethoxide cyclizes to 3-(α-ethylbenzyl)-2-carboethoxy-4-hydroxycoumarin
(24.1.13). Alkaline hydrolysis of this product and further decarboxylation gives phenprocoumon(24.1.14).
Check Digit Verification of cas no
The CAS Registry Mumber 435-97-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 435-97:
(5*4)+(4*3)+(3*5)+(2*9)+(1*7)=72
72 % 10 = 2
So 435-97-2 is a valid CAS Registry Number.
InChI:InChI=1/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
435-97-2Relevant articles and documents
An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes
Chatterjee, Rana,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Chupakhin, Oleg N.,Majee, Adinath
, p. 123 - 124 (2021/02/16)
An efficient straightforward solvent-free C(3)-benzylation of 4-hydroxycoumarin with styrenes is performed by heating the reactants in the presence of p-toluenesulfonic acid. By this procedure, benzylated 4-hydroxycoumarin derivatives which exhibit variou
Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
supporting information, p. 3911 - 3914 (2018/07/22)
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
Synthesis method of propafenone drug intermediate 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin
-
Paragraph 0014; 0015; 0006, (2016/11/21)
A synthesis method of a propafenone drug intermediate 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin includes the following steps that 0.21 mol of 4-hydroxyl coumarin and 0.26-0.29 mol of alpha-ethyl benzyl amine are added into a reaction vessel, the solution temperature is raised to 110-115 DEG C, the reaction time is 3-5 hours, the solution temperature is reduced to 10-15 DEG C, 300 ml of a potassium sulfite solution is added, acetonitrile is used for extracting the excessive alpha-ethyl benzyl amine, the solution is poured into 1.3 L of an oxalic acid solution, solid precipitation, filtration and washing with a saline solution are performed, a filter cake is added into 2.3 L of a potassium bromide solution, the solution temperature is raised to 90-95 DEG C and is kept for 2-3 hours, the solution temperature is reduced to 5-9 DEG C, solid precipitation, washing with cyclohexane and dehydration with a dehydrating agent are performed, and recrystallization is performed in nitromethane to obtain the crystal 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin.
