On the fluorescence reaction of pharmaceutically important o-aminobenzamides and o-aminobenzenesulfonamides with phthalaldehyde and analogues

In order to develop a specific TLC-fluorescence detection drugs such as Quinethazone (1a), Fenquizone (1b), Diazoxide (7), Bendroflumethiazide (11a), Hydrochlorothiazide (11b) and their derivatives were hydrolysed to provide o-aminobenzamide 2 and o-aminobenzenesulfimades 8, 12, and 13. The reaction...

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Bibliographic Details
Published inArchiv der Pharmazie (Weinheim) Vol. 328; no. 11-12; pp. 759 - 764
Main Authors Troschutz, R, Heinemann, O
Format Journal Article
LanguageEnglish
Published DEERFIELD BEACH Wiley 1995
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
phthalaldehyde
o-aminobenzenesulfonamides
fluorescence reaction
o-aminobenzamides
3-benzoylpyridine-2-carbaldehyde
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Summary:In order to develop a specific TLC-fluorescence detection drugs such as Quinethazone (1a), Fenquizone (1b), Diazoxide (7), Bendroflumethiazide (11a), Hydrochlorothiazide (11b) and their derivatives were hydrolysed to provide o-aminobenzamide 2 and o-aminobenzenesulfimades 8, 12, and 13. The reaction of these 1,5-N-bisnucleophiles with phthaladehyde (3a) and analogues 3b-e resulted in weak up to intensive fluorescent products 5, 9, 14, 15. Applying this method do Diazoxide capsules, 5 ng of Diazoxide (7) could be detected by pre- and postchromatographic derivatisation with 3-benzoylpyridine-2-carbaldehyde (3e) on TLC plates. The reaction of o-aminobenzenesulfonamide 8 with 3,4-dimethoxyphthaladehyde (3b) in CD3OD/DCl provided a monodeuterated compound 10b. N,N-Acetals 17,18, and 19 were obtained from the reaction of furan-3,4-dicarbaldehyde (16) with o-aminobenzenesulfonamides 8,12, and 13 in MeOH/20 degrees C.
ISSN:0365-6233
DOI:10.1002/ardp.19953281106