3200-06-4 Usage
Chemical Properties
White solid
Originator
Dusodril,Roland,W. Germany,1968
Uses
antineoplastic
Manufacturing Process
30 grams (0.106 mol) of β-(1-naphthyl)-β'-tetrahydrofuryl isobutyric acid are
heated under reflux for 8 1/2 hours in 230 cc of isopropanol with 14 grams
(0.103 mol) of β-chloroethyl-N-diethylamine. After evaporation of the
isopropanol in vacuo, the syrupy residue is treated with a solution of K2CO3.
Extraction with ether is carried out after drying over Na2SO4.Distillation of the extract yields 28.5 grams of a very viscous yellow liquid with
a BP0.95-1.09millibar = 198° to 202°C. The yield is 70.5% (theoretical quantity =
40.5 grams).1.3 grams (0.0103 mol) of dihydrated oxalic acid are dissolved
while being made tepid in 8 cc of acetone. The cooled solution has added
thereto 4 grams (0.0104 mol) of N-diethylaminoethyl-β-(1-naphthyl)-β'-
tetrahydrofuryl isobutyrate, obtained according to the process described above
and dissolved in 10 cc of acetone. The solution is brought to boiling point for
15 minutes. After cooling to ambient temperature, it is placed in a
refrigerator. Crystallization occurs after 2 hours, the crystals which have
formed are separated by centrifuging, and after washing in hexane and drying
in vacuo 3.5 grams of white crystals are obtained. After being recrystallized
three times, in alcohol and then in a mixture of alcohol and ethyl acetate, the
product is analytically pure and has a MP = 110° to 111°C (heating stage).
Brand name
Praxilene (Lipha, S.A., France).
Therapeutic Function
Vasodilator
Clinical Use
Vasodilator:
Peripheral and cerebral vascular disease
Drug interactions
Potentially hazardous interactions with other drugs
None known
Metabolism
Metabolised by plasma pseudo-cholinesterases to 3 active
metabolites.
Check Digit Verification of cas no
The CAS Registry Mumber 3200-06-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,0 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3200-06:
(6*3)+(5*2)+(4*0)+(3*0)+(2*0)+(1*6)=34
34 % 10 = 4
So 3200-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C24H33NO3.C2H2O4/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20;3-1(4)2(5)6/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;(H,3,4)(H,5,6)/p-1
3200-06-4Relevant articles and documents
Separation of Stereoisomeric Mixtures of Nafronyl as a Representative of Compounds Possessing Two Stereogenic Centers by Coupling Crystallization, Diastereoisomeric Conversion and Chromatography
Kiwala, Dawid,Olbrycht, Maksymilian,Balawejder, Maciej,Piatkowski, Wojciech,Seidel-Morgenstern, Andreas,Antos, Dorota
, p. 615 - 625 (2016/04/04)
A procedure for the isolation of the most biologically active component of a stereoisomeric mixture of nafronyl-2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoate has been proposed. The molecule of nafronyl is a representative of compounds possessing two stereogenic centers, which may be produced in the form of a quaternary mixture that contains two pairs of racemates being diastereoisomers of one another. The components of such stereoisomeric mixtures usually differ in pharmacological activity; therefore, there is an interest in developing efficient methods for their resolution. The method suggested in this study comprised two sequential separation processes, including multistage cross-current crystallization and chiral chromatography. Crystallization was employed to enrich the raw material mixture with the target racemate, which contained the stereoisomer exhibiting the highest biological activity. To intensify the process, the mother liquors depleted with the target racemate were subjected to fast base-catalyzed diastereoisomeric conversion in the melt, which provided equimolar mixtures of all four stereoisomers. The coupling of cross-current crystallization and diastereoisomeric conversion could improve yield of crystallization from 29% up to 84%. The purified racemate was further processed by chromatography to isolate finally the most active stereoisomer with 99% purity and total yield of 84%, at a relatively high throughput.
