- Process for the preparation of di- and trialkyl-4'-phthalimidomethylfurocoumarins
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Di- and trialkyl-4'-phthalimidomethyl-furocoumarins are prepared by reacting di- or trialkyl-furocoumarins in the presence of an acid and, if appropriate, of a polar solvent with a compound of the formula (I) STR1 in which R" represents hydrogen, a second phthalimidomethyl group, C1 - to C4 -alkyl or C1 - to C6 -acyl, where, when using trialkyl-furocoumarins, R" does not represent hydrogen.
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- Psoralens aminomethylation
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A direct, acid-catalyzed substitution reaction incorporates an N-phthalimidomethyl group on the 4' or 5' carbon of a psoralen in yields of 60-80% via the condensation of an N-hydroxymethylamide or phthalimide (e.g. N-hydroxymethylphthalimide) and an appropriately substituted psoralen. The phthalimide moiety is cleaved from the psoralen ring by treatment with hydrazine to give 60 to 70% yields of the aminomethylpsoralens.
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- Psoralens
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New psoralen compounds have been synthesized. The compounds all include the addition of substituent groups at the 4'-position on the basic trioxsalen structure. Specifically, the compounds have the structure STR1 wherein STR2 where R is a mono or dicyclic radical which can contain one additional hetero atom in the nitrogen containing ring. The new substituted psoralens exhibit high solubility in aqueous solution and low dissociation constants from deoxyribonucleic acid (DNA), as well as a reactivity with ribonucleic acids (RNA).
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- Psoralens
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New psoralen compounds have been synthesized. The compounds all include the addition of substituent groups at the 4' position on the basic trioxsalen structure. Specifically, the compounds have the structure: STR1 wherein X may be any desired substituent such as halogenated alkyls, alcohols, ethers, aminoalkyls, etc. The new substituted psoralens exhibit high solubility in aqueous solution and low dissociation constants from deoxyribonucleic acid (DNA), as well as a reactivity with ribonucleic acids (RNA). Such psoralen compounds find use in the study of secondary structures of nucleic acids; as inhibitors of RNA replication; in the inactivation of viruses; and in the photo chemotherapy of psoriasis.
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