Psoralen synthesis. Improvements in furano ring formation. Application to the synthesis of 4,5',8-trimethylpsoralen

Bender, Dean R.; Hearst, John E.; Rapoport, Henry

doi:10.1021/jo01327a030

Cited by 29 publications

(16 citation statements)

References 10 publications

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“…The two most widely used psoralens are 8-methoxypsoralen, isolated from Ammi Majus, and 4,5' ,8trimethylpsoralen, derived from a fungus which grows on diseased celery (57). Both of these compounds are readily prepared by chemical synthesis (58)(59)(60).…”

Section: Naturally Occurring Psoralensmentioning

confidence: 99%

See 1 more Smart Citation

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

Cimino

Gamper

Isaacs

et al. 1985

Annu. Rev. Biochem.

750

361

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Section: Naturally Occurring Psoralensmentioning

confidence: 99%

“…number of methods have been developed for the addition of the furan ring to the coumarin. Psoralens and isopsoralens containing alkyl groups at the 41 or 5' positions (60,63,71) or with an unsubstituted furan ring have been prepared (72,73).…”

Section: Synthesis and Radiolabeling Of Psoralensmentioning

confidence: 99%

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

Cimino

Gamper

Isaacs

et al. 1985

Annu. Rev. Biochem.

750

361

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“…The unusually complete state of knowledge regarding psoralen photochemistry has been achieved in the last three years, primarily as a result of the efforts of those in this laboratory. These achievements have included new methods of organic synthesis and structural modification which are not discussed here but can be found in appropriate references (Bender, Rapoport & Hearst, 1979). Methods for radiolabelling psoralens have played an essential role in the isolation and purification of the photoproducts of the reactions between psoralens and nucleic acids and have been reviewed here.…”

mentioning

confidence: 99%

The reaction of the psoralens with deoxyribonucleic acid

Hearst

Isaacs

Kanne

et al. 1984

Quart. Rev. Biophys.

Self Cite

158

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Psoralen photochemistry is specific for nucleic acids and is better understood at the molecular level than are all other methods of chemical modification of nucleic acids. These compounds are used both for in vivo structure analysis and for photochemotherapy since they easily penetrate both cells and virus particles. Apparently, natural selection has selected for membrane and virus penetrability during the evolution of these natural products. Most cells are unaffected by relatively high concentrations of psoralens in the absence of ultraviolet light, and the metabolites of the psoralens have thus far not created a problem. Finally, psoralens form both monoadduct and cross-links in nucleic acid helices, the yield of each being easily controlled by the conditions used during the photochemistry.

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“…Compounds 2 a [20], 2 b [21], 2 c [24], 2 g [21], 2 h [21], and 2 j [25] were prepared according to general procedure for preparation of β-ketoethers [43]. Compounds 3 a [20], 3 b [21], 3 c [24], 3 g [21], and 3 h [21] were prepared according to general procedure for preparation of 7H-furo[3,2-g]-1-benzopyran-7-ones [21].…”

Section: Chemistrymentioning

confidence: 99%

3-Alkyl- and 3-Aryl-7H-furo[3, 2-g]-1-benzopyran-7-ones: Synthesis, Photoreactivity, and Fluorescence Properties

Korner

2002

Arch. Pharm. Pharm. Med. Chem.

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A series of 3‐alkyl‐ and 3‐aryl‐7H‐furo[3, 2‐g]‐1‐benzopyran‐7‐ones, known as linear furocoumarins, was synthesized and evaluated for their dark‐ and photobinding (crosslink formation) with DNA as well as for their spectrophotometric and fluorescent properties, lipophilicity, and ability to photobleach N, N‐dimethyl‐p‐nitrosoaniline (RNO) after irradiation with UVA light. 8‐Methoxypsoralen (8‐MOP, 9‐methoxy‐7H‐furo[3, 2‐g]‐1‐benzopyran‐7‐one) and 4, 5′, 8‐trimethylpsoralen (TMP, 2, 5, 9‐trimethyl‐7H‐furo[3, 2‐g]‐1‐benzopyran‐7‐one) were used as reference compounds in all tests. The investigations support the formation of a molecular complex between the furocoumarins and DNA.Crosslink formation with DNA after irradiation with UVA light was detectable for compounds with a methyl or phenyl substituent in position 3, but not for those bearing either a tert‐butyl, a 4‐methoxyphenyl, or a 2, 5‐dimethoxyphenyl group. All furocoumarins exhibited sufficient absorption in the UVA wavelength range and are fluorescent. All compounds showed a higher lipophilicity than 8‐MOP. Generally the 3‐alkyl substituted furocoumarins had a capacity to photobleach RNOwhich was higher than that of the 3‐aryl substituted ones. Some of the 3‐aryl substituted furocoumarins displayed a photobleaching ability which was similar to or lower than that of 8‐MOP.

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Psoralen synthesis. Improvements in furano ring formation. Application to the synthesis of 4,5',8-trimethylpsoralen

Cited by 29 publications

References 10 publications

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

The reaction of the psoralens with deoxyribonucleic acid

3-Alkyl- and 3-Aryl-7H-furo[3, 2-g]-1-benzopyran-7-ones: Synthesis, Photoreactivity, and Fluorescence Properties

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