58473-74-8 Usage
Description
TRANS-3-BROMO-N-ETHYLCINNAMAMIDE is a chemical compound with the molecular formula C10H10BrNO. It is a derivative of cinnamic acid, featuring a bromine atom at the 3-position and an ethyl group attached to the nitrogen atom. TRANS-3-BROMO-N-ETHYLCINNAMAMIDE exhibits a range of biological activities and has potential applications in various fields.
Uses
Used in Pharmaceutical Industry:
TRANS-3-BROMO-N-ETHYLCINNAMAMIDE is used as a bone resorption inhibitor for preventing the breakdown of bone tissue, which can be beneficial in treating conditions like osteoporosis and Paget's disease of bone.
Used in Pharmaceutical Industry:
TRANS-3-BROMO-N-ETHYLCINNAMAMIDE is used as a farnesyldiphosphate synthetase inhibitor, which can help regulate the mevalonate pathway and potentially lead to the development of new therapeutic agents for various diseases.
Used in Pharmaceutical Industry:
TRANS-3-BROMO-N-ETHYLCINNAMAMIDE is used as an antimetastatic agent, which can help prevent the spread of cancer cells to other parts of the body, thus reducing the severity and progression of metastatic diseases.
Used in Pharmaceutical Industry:
TRANS-3-BROMO-N-ETHYLCINNAMAMIDE is used as an anticonvulsant, similar to cinromide, for the treatment of epilepsy and other seizure disorders. It may help control seizures by stabilizing the electrical activity in the brain.
Originator
Cinromide,ZYF Pharm Chemical
Manufacturing Process
3-Bromo-N-ethylcinnamamide:
I). A solution of trans-3-bromocinnamoyl chloride (12.3 g) in anhydrous
toluene (150 ml) was added slowly with stirring to a solution of ethylamine
(10 g) in dry ether (100 ml) at room temperature. The reaction mixture was
heated at reflux for 1 hour, and the solvent and excess amine were then
removed under reduced pressure. The residue was triturated with water,
filtered, and recrystallized from ethanol-water to give trans-3-bromo-Nethylcinnamamide, m.p. 89-90°C, as a white crystalline material. NMR and IR
spectra as well as elemental analysis were consistent with the assignedII). trans-m-Bromocinnamic acid (14.8 g), ethanol (173 ml) and concentrated
sulfuric acid (0.4 ml) were combined and heated at reflux for 15 hours. About
150 ml of the ethanol was distilled off, and the remaining solution was poured
into ice/water (140 ml). The cold mixture was made strongly alkaline with
40% sodium hydroxide and extracted with methylene chloride (4x60 ml). The
combined methylene chloride extract was dried over anhydrous potassium
carbonate. The potassium carbonate was removed by filtration and the solvent
stripped off under reduced pressure. trans-ethyl-3-Bromocinnamate, was
obtained as a partially solidified oil. (IR spectrum was consistent with this
compound).
trans-Ethyl-3-bromocinnamate (8.4 g), ethylamine (6.7 g), methanol (18 ml)
and 4A molecular sieves (1 g) were combined and heated at reflux for ? hour.
The mixture was cooled to about 45°C and sodium methylate (0.6 g) added.
The mixture was then heated at reflux 1? hour and then cooled. It was
acidified with concentrated hydrochloric acid (12 ml). The sieves were
removed by filtration. Ice water was added to the filtrate to precipitate trans
3-bromo-N-ethylcinnamamide, m.p. 89-90°C (after recrystallization from
ethanol/water)
Check Digit Verification of cas no
The CAS Registry Mumber 58473-74-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,4,7 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 58473-74:
(7*5)+(6*8)+(5*4)+(4*7)+(3*3)+(2*7)+(1*4)=158
158 % 10 = 8
So 58473-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H12BrNO/c1-2-13-11(14)7-6-9-4-3-5-10(12)8-9/h3-8H,2H2,1H3,(H,13,14)/b7-6+
58473-74-8Relevant articles and documents
Anti-convulsant cinnamide compounds
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, (2008/06/13)
Cinnamamide compounds of the formula STR1 where X is chloro, bromo or iodo and R is hydrogen or alkyl of 1 to 3 carbons As pharmaceuticals which are useful in the treatment or prophylaxis for convulsions.
