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 beta-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protocol which has led to the synthesis of analogues of tetrahydropapaverine in which the dimethoxybenzene moiety has been replaced by substituted coumarins.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.
Jadhav
Vithal B
VB
Department of Chemistry, Karnatak Univeristy, Pawate Nagar, Dharwad, Karnataka 580 003, India.
Nayak
Susanta K
SK
Row
T N Guru
TN
Kulkarni
M V
MV
D001234:Aspergillus niger; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D003374:Coumarins / Q000737:chemistry*; D004269:DNA, Bacterial / Q000737:chemistry / Q000378:metabolism*; D004271:DNA, Fungal / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli; D013211:Staphylococcus aureus; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*
D001600:Berberine Alkaloids; D003374:Coumarins; D004269:DNA, Bacterial; D004271:DNA, Fungal; D044005:Tetrahydroisoquinolines; C009090:protoberberine; C030123:coumarin