64748-79-4 Usage
Originator
Azumolene sodium,ZYF Pharm Chemical
Uses
Relaxant (skeletal muscle).
Manufacturing Process
To a stirred solution of 2-bromo-4'-bromoacetophenone (100.0 g, 0.36 mole)
in chloroform (500 ml) was added hexamethylenetetramine (50.0 g, 0.36
mole). The mixture was stirred for 2.5 h and 143.0 g of the product was
collected by filtration (100%).
The product above was combined with a solution of methanol (300 ml) and
conc. HCl (410 ml), and the mixture was stirred for 52 h. The solid was
collected by filtration and was washed with isopropanol. The product was
recrystallized from methanol (Darco) to give 55.0 g (61%, in three crops),
melting point 284°-287°C.
To a stirred mixture of the above amine hydrochloride (55.0 g, 0.22 mole) and
[[(2,4-dioxo-1-imidazolidinyl)imino]methyl]formyl chloride (42.0 g, 0.22 mole)
was added a solution of 440 ml of dimethylformamide and 44 ml of pyridine.
The mixture was stirred for 20 h and poured into 2 L of water. The solid was
collected by filtration and washed with ethanol and ether to give 36.0 g (28%)
of N-[2-(4-bromophenyl)-2-oxoethyl]-[[(2,4-dioxo-1-imidazolidinyl)-
imino]methyl]formamide, melting point 267°-269°C (recrystallization from
2200 ml acetic acid).
The of N-[2-(4-bromophenyl)-2-oxoethyl]-[[(2,4-dioxo-1-imidazolidinyl)
imino]methyl]formamide (22.0 g, 0.061 mole) was combined with phosphorus
oxychloride (310 ml) and the mixture was stirred and refluxed for 7 h. The
solid was filtered off and stirred into an ice and water mixture (1 L). The 15.0
g (70%) of 1-[[[5-(4-bromophenyl)-2-oxazolyl]methylene]amino]-2,4-
imidazolidinedione was collected by filtration, melting point 290°-292°C
(recrystallization from 700 ml acetic acid).
Therapeutic Function
Muscle relaxant
Biochem/physiol Actions
Azumolene, a more water-soluble analog of dantrolene, is a potent inhibitor of sarcoplasmic reticulum (SR) ryanodine receptor (RyR) that inhibits skeletal muscle SR Ca2+ release. Azumolene is a direct acting skeletal muscle relaxant that induces effective blockade of skeletal muscle RyR1.
Check Digit Verification of cas no
The CAS Registry Mumber 64748-79-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,7,4 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 64748-79:
(7*6)+(6*4)+(5*7)+(4*4)+(3*8)+(2*7)+(1*9)=164
164 % 10 = 4
So 64748-79-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H9BrN4O3/c14-9-3-1-8(2-4-9)10-5-15-12(21-10)6-16-18-7-11(19)17-13(18)20/h1-6H,7H2,(H,17,19,20)
64748-79-4Relevant articles and documents
1-methylene>amino>-2,4-imidazolidinediones, a New Class of Skeletal Muscle Relaxants
White, R.L.,Wessels, F.L.,Schwan, T.J.,Ellis, K.O.
, p. 263 - 266 (2007/10/02)
A series of 1-methylene>amino>-2,4-imidazolidinediones (6a-t) was synthesized, and the compounds were evaluated for direct skeletal muscle inhibition in the pithed rat gastrocnemius muscle preparation.The correctness of structural assignment of the new series was verified by alternate, unequivocal synthesis of one representative structure (6f).The phenyloxazoles 6d, 6g, 6j, 6k,and 6l exhibited significant skeletal muscle relaxant activity when administered intravenously and orally.The skeletal muscle relaxant effect of these five compounds is similar to that of other direct-acting skeletal muscle relaxants.The oxazole moiety proved to be an acceptable isosteric replacement for furan, as the biological activity in the oxazole series was retained.The synthesis of this new class of compounds is described, and pharmacologic evaluation data are presented.A discussion of structure-activity relationships is also presented.
