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Difurocoumarins: Psoralen analogs as photochemotherapeutic agents
Author(s) -
Chilin A.,
Manzini P.,
Caffieri S.,
Rodighiero P.,
Guiotto A.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380219
Subject(s) - psoralen , chemistry , coumarin , intercalation (chemistry) , furan , dna , stereochemistry , nucleus , combinatorial chemistry , organic chemistry , biochemistry , biology , microbiology and biotechnology
New tetracyclic psoralen‐like compounds have been synthesized, which are characterized by two furan rings angularly condensed on the coumarin nucleus and are therefore called difurocoumarins. This structural feature may favour the intercalation into the DNA helix and then monofunctionally photoreaction with DNA bases. Their synthesis started from 5,7‐dihydroxy‐4‐methylcoumarin, which was condensed with α‐halo‐ketones; the resulting ketoethers were then cyclized to give the title compounds.