Abstract
Two aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines A and B have been synthesized. The strategy used was based on a 1,3-dipolar cycloaddition reaction between indole 4,7-dione and a diazo-aminopropane derivative. One of the two analogues partially inhibits human topoisomerase I, whereas synthetic intermediates inhibit the enzyme DNA cleavage activity at a concentration comparable to that of the control drug camptothecin.
MeSH terms
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Animals
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Aza Compounds / chemical synthesis*
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Aza Compounds / chemistry
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Aza Compounds / pharmacology
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Cyclization
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Humans
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry
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Indole Alkaloids / pharmacology
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Molecular Structure
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry*
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Pyrroles / pharmacology
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Quinolines / chemical synthesis*
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Quinolines / chemistry*
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Quinolines / pharmacology
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Structure-Activity Relationship
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Topoisomerase I Inhibitors*
Substances
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Aza Compounds
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Indole Alkaloids
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Pyrroles
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Quinolines
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Topoisomerase I Inhibitors
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pyrroloquinoline
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tsitsikammamine A
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tsitsikammamine B
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wakayin