Photochemistry of Stilbenes. III. Some Aspects of the Mechanism of Photocyclization to Phenanthrenes

Mallory, Frank B.; Wood, Clelia S.; Gordon, John H.

doi:10.1021/ja01069a025

Cited by 275 publications

(147 citation statements)

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“…The early method of thin layer chromatography, and the current method of high performance liquid chromatography (HPLC) both depend on the conversion of the triphenylethylenes to fluorescent phenanthrenes for their detection ( Figure 6). The original description of the reaction [88] was successfully adapted [89] to identify tamoxifen, N-desmethytamoxifen and 4-hydroxytamoxifen in plasma samples.…”

Section: Clinical Pharmacologymentioning

confidence: 99%

New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer

2007

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The metabolism of tamoxifen is being redefined in the light of several important pharmacological observations. Recent studies have identified 4-hydroxy N-desmethyl tamoxifen (endoxifen) as an important metabolite of tamoxifen necessary for antitumor actions. The metabolite is formed through the enzymatic product of CYP2D6 which also interacts with specific selective serotonin reuptake inhibitors (SSRIs) used to prevent the hot flashes observed in up to 45% of patients taking tamoxifen. Additionally, the finding that enzyme variants of CYP2D6 do not promote the metabolism of tamoxifen to endoxifen means that significant numbers of women might not receive optimal benefit from tamoxifen treatment. Clearly these are particularly important issues not only for breast cancer treatment but also for selecting premenopausal women, at high risk for breast cancer, as candidates for chemoprevention using tamoxifen.

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Section: Clinical Pharmacologymentioning

confidence: 99%

New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer

2007

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“…The photocyclization and oxidation of substituted stilbenes have been shown to give substituted phenanthrenes (I), provided one of the substituents is not a nitro group (2). The photocyclization-oxidation reaction of 1,4-diaryl-1,3-butadienes, where the aryl groups are phenyl or substituted phenyl groups, gave mixtures of substituted 1-phenylnaphthalenes (3,4).…”

Section: Introductionmentioning

confidence: 99%

Photocyclization Reactions of Aryl Polyenes. IV. The Syntheses of Isatogens and Isatogen-like Compounds

Leznoff¹,

Hayward²

1971

Can. J. Chem.

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“…39,40 The multistep conversion comprises isomerization of E-stilbenes to Z-stilbenes, followed by cyclization of intermediate radicals to dihydrophenanthrenes that are irreversibly dehydrogenated to phenanthrenes in the presence of oxidants. 37 The stilbenes 84-87 required for our investigation were prepared by Wittig reaction using the procedure of The preferential formation of the less hindered regioisomer has also been observed in hydroxylated precursors. 7 A methoxy group was eliminated during the irradiation of 87 yielding the 1,2,6,7-tetramethoxyphenanthrene 91.…”

Section: Photocyclizationmentioning

confidence: 99%

Synthesis and electrochemistry of annoquinone-A, cypripedin methyl ether, denbinobin and related 1,4-phenanthrenequinones

Krohn¹,

Loock²,

Paavilainen³

et al. 2001

Arkivoc

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The natural product annoquinone-A (1), the 1,4-phenanthrenequinones 41-75 and the 9,10-dihydro-1,4-phenanthrenequinones 76-81 were prepared by Diels-Alder reaction of the styrenes 23-37 with the benzoquinones 38-40. The sterically hindered 5-methoxy compounds, which adopt a twisted conformation as shown by X-ray analysis, are only formed in trace amounts or as the less hindered 9,10-dihydro-1,4-phenanthrenequinones 76-81. The twisted conformation also leads to characteristic changes in the NMR spectra and the redox potential. Reaction of methoxybenzoquinone with styrenes preferentially affords the 3-methoxy-1,4-phenanthrenequinones. Selective ether cleavage of the 5-methoxy group in 60 leads to the natural product denbinobine (3). Small amounts of C-9 hydroxylated compounds (57, 66, 68, 73, and 75) were also formed in the Diels-Alder reactions. In an alternative synthesis, using the photocylization of the stilbenes 84-87 followed by CAN oxidation, the 1,4-phenanthrenequinones 45, 51, 59 [methyl ether of cyprepidine (2)

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Photochemistry of Stilbenes. III. Some Aspects of the Mechanism of Photocyclization to Phenanthrenes

Cited by 275 publications

References 0 publications

New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer

New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer

Photocyclization Reactions of Aryl Polyenes. IV. The Syntheses of Isatogens and Isatogen-like Compounds

Synthesis and electrochemistry of annoquinone-A, cypripedin methyl ether, denbinobin and related 1,4-phenanthrenequinones

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