Abstract:
:6-(1-Acyloxyalkyl)-5,8-dimethoxy-1,4-naphthoquinone (DMNQ; 5,8-dimethoxy-1,4-naphthoquinone) derivatives were synthesized and examined for their inhibitory effect on DNA topoisomerase-I (Topo I) and their antiproliferative activity against L1210 cells. The Topo-I inhibitory effect of 6-(1-hydroxyalkyl)-DMNQ derivatives was found to be dependent on the size of the alkyl chains, suggesting that lipophilicity might be one important factor influencing the inhibitory effect. It was found that acylation of 6-(1-hydroxyalkyl)-DMNQ derivatives possessing alkyl chains of C2-C5 enhanced both bioactivities, suggesting that an increase of electrophilicity in the quinoid moiety makes the electrophilic arylation of bionucleophiles more favorable. It is noteworthy that 6-(1-heptanoyloxyethyl)-DMNQ exhibited both the most potent Topo I inhibitory activity (IC50, 11.5 microM) and the greatest antiproliferative activity (ED50, 0.05 microM) upon L1210 cells.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Kim Y,You YJ,Ahn BZdoi
10.1002/1521-4184(200110)334:10<318::aid-ardp318>3keywords:
subject
Has Abstractpub_date
2001-10-01 00:00:00pages
318-22issue
10eissn
0365-6233issn
1521-4184pii
10.1002/1521-4184(200110)334:10<318::AID-ARDP318>3journal_volume
334pub_type
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