2165-19-7 Usage
Originator
Envacar,Pfizer
Uses
Guanoxan is a sympatholytic drug related to Guanethidine (G815000). Guanoxan is used in the treatment of hypertension.
Manufacturing Process
2 Methods of producing of 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine:
1. 3.3 parts by weight of 2-aminomethyl-1,4-benzodioxane and 2.78 parts by
weight of S-methylisothiouronium sulfate were dissolved in 20 parts by
volume of water, and the resulting aqueous solution was heated under reflux
for 3 h. At the end of this time, the solvent was removed by means of
evaporation under reduced pressure and the residue so obtained dissolved in
a minimum amount of fresh water and treated with charcoal. Upon filtration,
there was obtained a clear filtrate which, on standing, soon afforded pure
crystals of di(2-guanidinomethyl-1,4-benzodioxane)sulfate, melting point
204°-205°C.
The base 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine may be obtained
by reaction of di(2-guanidinomethyl-1,4-benzodioxane)sulfate with, for
example, sodium hydroxide.
2. o-Dihydroxybenzene reacted with epichlorhydrine in the presence sodium
hydroxide and 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine was obtained.
To solution of 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine thionylchloride
was added to give 2-chlormethyl-2,3-dihydro-1,4-benzodioxine.
2-Chloromethyl-2,3-dihydro-1,4-benzodioxine reacted with benzylamine to
produced 2-benzylaminomethyl-2,3-dihydro-1,4-benzodioxine, which was
reduced at the presence of hydrogen and Pd-C (catalyst) to 2-aminomethyl-
2,3-dihydro-1,4-benzodioxine.
2-Aminomethyl-2,3-dihydro-1,4-benzodioxine was treated by Smethylisothiouronium sulfate and there was produced 2-guanidinemethyl-2,3-
dihydro-1,4-benzodioxine.
Brand name
Envacar (Pfizer).
Therapeutic Function
Antihypertensive
Check Digit Verification of cas no
The CAS Registry Mumber 2165-19-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,6 and 5 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2165-19:
(6*2)+(5*1)+(4*6)+(3*5)+(2*1)+(1*9)=67
67 % 10 = 7
So 2165-19-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H13N3O2/c11-10(12)13-5-7-6-14-8-3-1-2-4-9(8)15-7/h1-4,7H,5-6H2,(H4,11,12,13)
2165-19-7Relevant articles and documents
N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors
Xian, Ming,Li, Xiaopeng,Tang, Xiaoping,Chen, Xinchao,Zheng, Zhongling,Galligan, James J,Kreulen, David L,Wang, Peng G
, p. 2377 - 2380 (2007/10/03)
Recent research suggests that NO may play a role in the physiological effects of some guanidine-containing drugs. In this report, three guanidine-containing drugs (guanadrel, guanoxan, and guanethidine) together with their N-hydroxyl derivatives were synthesized and their NO-releasing abilities catalyzed by nitric oxide synthases (NOSs) and horseradish peroxidase were evaluated. The guanidine containing compounds could not release NO in the presence of NOS or peroxidase. The corresponding N-hydroxyl compounds exhibited weak NO-releasing ability under the catalyzed of NOS and good NO-releasing ability under the oxidation by horseradish peroxidase in the presence of H2O2. These compounds also displayed vasodilatory activity. Elsevier Science Ltd. All rights reserved.
THE SYNTHESIS AND PHARMACOLOGY OF SOME SUBSTITUTED 1,3-BENZODIOXOLES
BAINES,COBB,EDEN,FIELDEN,GARDNER,ROE,TERTIUK,WILLEY
, p. 81 - 90 (2007/10/04)
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