Dye-sensitized photooxidation of 1-methylindolyl-3-acetic acid

Amat‐Guerri, F.; López-González, M.M.C.; Martínez-Utrilla, R.

doi:10.1016/s0040-4039(00)94525-8

Cited by 6 publications

(7 citation statements)

References 11 publications

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“…Our results on the effects of pH on the oligomerization process are an extension of the findings of Amat-Guerri et al (15) and provide evidence for a mechanistic rationale for the observed product distribution. Under neutral conditions no polymerization beyond the dimer is observed, and under weakly acidic conditions (pH 5) dimer and LTr!…”

Section: Discussionsupporting

confidence: 87%

“…Under neutral conditions no polymerization beyond the dimer is observed, and under weakly acidic conditions (pH 5) dimer and LTr! are formed almost exclusively (15). As the pH is lowered further, yields of ICZ and larger oligomers are increased relative to that of 3,3'-DIM.…”

Section: Discussionmentioning

confidence: 94%

“…However, ICZ is produced in approx-imately 20% yield by reaction in strongly acidic methanol solutions of indole and formaldehyde or of 3,3'-DIM by itself, if the reactions are run in the presence of light, oxygen, and photosensitizer (14). Indoles are highly reactive under these photodynamic conditions (15). In addition, Rannug et al have reported the conversion of tryptophan under photodynamic conditions to unidentified products with high affinity for the Ah receptor (16).…”

Section: Discussionmentioning

confidence: 99%

“…Compound f (LTet): m/z 516 (1), 504 (6, M+), 387 (21), 375 (13), 372 (12), 259 (22), 258 (100), 257 (86), 256 (41), 246 (15), 245 (31), 243 (12), 130 (32); exact mass caled for Cg5H28N4: 504.2314; found: 504.2318.…”

Section: Methodsmentioning

confidence: 99%

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Oligomerization of indole-3-carbinol in aqueous acid

Grose

Bjeldanes²

1992

Chem. Res. Toxicol.

201

129

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Indole-3-carbinol [I3C, also called 3-(hydroxymethyl)indole] is a naturally occurring modulator of carcinogenesis with a biological activity that is at least partially dependent on its conversion to active substances in acidic media. We compared the identities of the major oligomeric products of I3C produced under conditions approximating those found in gastric juice with the reported identities of products of 3-substituted indoles produced under enzymatic and other nonenzymatic conditions. After a 10-min treatment in aqueous HCl solution, I3C was converted in 18% yield to a mixture of acetonitrile-soluble products, the major components of which (as determined by HPLC) were diindol-3-ylmethane (5.9%), 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b"]triindo le (2.0%), and [2-(indol-3-ylmethyl)indol-3-yl]indol-3-ylmethane (5.9%). Tentative assignments were made for 3,3-bis(indol-3-ylmethyl)indolenine (0.59%), a symmetrical cyclic tetramer (0.64%), and a linear tetramer (1.1%). Indolo[3,2-b]carbazole (ICZ) was formed slowly in aqueous acidic solutions in low yields (2.0 ppm) which increased to greater than 90 ppm following addition of an organic solvent [tetrahydrofuran (THF) or dimethylformamide (DMF)] to a neutralized solution. Relative yields of trimers vs dimer increased with decreasing pH and with decreasing starting concentration of I3C. Evidence is presented that ICZ formation may not involve radical intermediates as is characteristic of photodynamic processes. A mechanistic rationale is presented for the formation of the identified products.

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Section: Discussionsupporting

confidence: 87%

Section: Discussionmentioning

confidence: 94%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Oligomerization of indole-3-carbinol in aqueous acid

Grose

Bjeldanes²

1992

Chem. Res. Toxicol.

201

129

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“…The same conversion can be realized by ozonolysis 161 , acidic bromate 162 or by a chemiluminescent autoxidation of indigo 163 . N-Methylisatin is also obtained in the photooxidation of N-methylindole-3-acetic acid 164 .…”

Section: Synthesis Of Oxindoles and Dioxindolesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

847

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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