54663-47-7 Usage
Originator
Antoral,Recordati,Italy,1977
Uses
Tibezonium Iodide is a possible inhibitor of Trypanosoma cruzi dihydrofolate reductase.
Manufacturing Process
4-Acetyldiphenylsulfide is reacted with carbon disulfide in an initial step to
give 4-phenylthiobenzoyl dithioacetic acid. That, in turn, is reacted with o_x0002_phenylenediamine.
A mixture of 3.6 g of the thus obtained 4-p-phenylthiophenyl-1,3-dihydro-2H-
1,5-benzodiazepine-2-thione, 0.50 g of 50% sodium hydride in oil and 200 ml
of benzene is refluxed for 30 minutes, then a solution of 2.02 g of β-
diethylaminoethyl chloride in 5 ml of benzene are added dropwise over 5
minutes.
The mixture is refluxed for 10 hours. The mixture is then cooled and filtered
to separate the sodium chloride. The filtrate is evaporated to dryness in
vacuo. The oily residue is dissolved in petroleum ether and the solution is
filtered with charcoal. The solvent is evaporated in vacuo. The oily residue is
heated to 50°C in vacuo (0.01 mm Hg) to remove the excess of β-
diethylaminoethyl chloride.
This treatment is continued until the β-diethylaminoethyl chloride disappears(TLC). The oil is then dissolved in isopropanol and weakly acidified with HCl in
propanol. The 2β-N-diethylaminoethylthio-4-p-phenylthiophenyl-3H-1,5-
benzodiazepine HCl product crystallizes by addition of anhydrous ethyl ether
to the solution. The crystals are filtered and recrystallized from ethyl acetate.
Yield 3.65 g, melting point 150°C.
2.55 g of methyl iodide are added to a solution of 5.93 g of 2-β-Ndiethylaminoethylthio-4-phenylthiophenyl-3H-1,5-benzodiazepine in 100 ml of
isopropanol. The mixture is kept at 20°C to 30°C for 60 hours. The crystals
are then filtered. Yield 6.2 g, melting point 161°C.
Therapeutic Function
Antimicrobial
Check Digit Verification of cas no
The CAS Registry Mumber 54663-47-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,6,6 and 3 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 54663-47:
(7*5)+(6*4)+(5*6)+(4*6)+(3*3)+(2*4)+(1*7)=137
137 % 10 = 7
So 54663-47-7 is a valid CAS Registry Number.
InChI:InChI=1/C28H32N3S2.HI/c1-4-31(3,5-2)19-20-32-28-21-27(29-25-13-9-10-14-26(25)30-28)22-15-17-24(18-16-22)33-23-11-7-6-8-12-23;/h6-18H,4-5,19-21H2,1-3H3;1H/q+1;/p-1
54663-47-7Relevant articles and documents
Thiabenzazonium, a new 1,5 benzodiazepine derivative with antimicrobial activity
Nardi,Massarani,Veronese,Degen,Setnikar
, p. 440 - 441 (2007/12/02)
The synthesis, physicochemical properties and antimicrobial activity of tibezonium iodide (thiabenzonium), a new quaternary ammonium derivative of 1,5 benzodiazepine, are described. Tibezonium iodide has high bacteriostatic and bactericidal activity against some gram positive bacteria which are agents of oropharyngeal infections.
