Synthesis and reactions of some new substituted 6-imidazolyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde and use of DNA in evaluation of their biological activity.
Vilsmeier-Haack reaction of imidazolyl acetophenone I gave 6-imidazolyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde II. The compound II was reacted with primary amines (1:1 molar ratio) to form the corresponding n-aril (meteroaryl) imino derivatives IIIa-f. Treatment of aldehyde II with excess amines (1:2 molar ratio) gave the corresponding 2-arylamino-3-arylaminomethylenebenzopyran derivatives IVa-c. The n-aril (meteroaryl) imino derivatives IIIb,d,e,f were reacted with thioglycollic acid to give benzopyranothiazepinone derivatives VIa-d. When the aldehyde II was treated with secondary amines gave the corresponding trans-enaminoketones VIIIa-c. Trans-enaminoketones VIIIa-c were reacted with hydrazines and/or hydroxylamine hydrochloride to give pyrazolyl and/or isoxazolyl benzene IXa-c and X, respectively. The reaction of aldehyde II with hydrazines on cold gave the corresponding hydrazones XIIIa-d. However, the reaction of aldehyde II with hydrazines on refluxing gave the corresponding pyrazole derivatives 5 XIVa,b and XVa,b.. The structural formula of the new compounds were established by using different instrumental analyses. Some compounds in this study were biologically evaluated for their ability to bind to DNA.
Abdel-Rahman
A H
AH
Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
Khalil
A M
AM
Keshk
E M
EM
D001578:Benzopyrans / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002867:Chromones / Q000138:chemical synthesis* / Q000494:pharmacology*; D003124:Colorimetry; D004247:DNA / Q000187:drug effects* / Q000378:metabolism; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008739:Methyl Green; D012394:Rosaniline Dyes; D013329:Structure-Activity Relationship
D001578:Benzopyrans; D002867:Chromones; D007093:Imidazoles; D012394:Rosaniline Dyes; D008739:Methyl Green; D004247:DNA