Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids

Novel molecular matrices have been derived from coumarin-4-acetic acids and β-phenylethylamines using the Bischler–Napieralski protocol which has led to the synthesis of analogues of tetrahydropapaverine in which the dimethoxybenzene moiety has been replaced by substituted coumarins. One carbon homo...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2010-09, Vol.45 (9), p.3575-3580
Main Authors: Jadhav, Vithal B., Nayak, Susanta K., Row, T.N. Guru, Kulkarni, M.V.
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Aspergillus niger
Berberine Alkaloids - chemical synthesis
Berberine Alkaloids - chemistry
Berberine Alkaloids - metabolism
Berberine Alkaloids - pharmacology
Biological and medical sciences
Coumarin-4-acetic acids
Coumarins - chemistry
DNA cleavage
DNA, Bacterial - chemistry
DNA, Bacterial - metabolism
DNA, Fungal - chemistry
DNA, Fungal - metabolism
Escherichia coli
General aspects
Medical sciences
Pharmacology. Drug treatments
Protoberberines
Staphylococcus aureus
Tetrahydroisoquinolines
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
Tetrahydroisoquinolines - metabolism
Tetrahydroisoquinolines - pharmacology
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Summary:Novel molecular matrices have been derived from coumarin-4-acetic acids and β-phenylethylamines using the Bischler–Napieralski protocol which has led to the synthesis of analogues of tetrahydropapaverine in which the dimethoxybenzene moiety has been replaced by substituted coumarins. One carbon homologation has led to cyclization at the C3 position of coumarin generating the protoberberine skeleton. Structures have been confirmed by diffraction studies. The results showed that compounds 6e, 6f, 7e and 7f were found to be very effective against DNA samples of Gram positive bacterium Staphylococcus aureus and fungus Aspergillus niger. A series of novel coumarin analogues of 1,2,3,4-tetrahydroisoquinoline and protoberberine alkaloids have been synthesized from coumarin-4-acetic acids. The DNA cleavage study has been performed on Gram positive, Gram negative bacteria and fungi strains. [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2010.04.041