ChemInform Abstract: ISOMERISIERUNG 3‐SUBSTITUIERTER INDOLE, BENZOFURANE UND BENZOTHIOPHENE

Кост, А. Н.; Budylin, V. A.; Matveeva, E. D.; Sterligov, D. O.

doi:10.1002/chin.197047187

Cited by 4 publications

(6 citation statements)

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“…Although 5-OHRA was first synthesized by Grese et al (37), we used a different synthetic procedure. The synthesis of differently substituted benzo[b]thiophene moieties was performed by the cyclization rearrangement induced by PPA, which has been described in the literature by Kost et al (38).…”

Section: Discussionmentioning

confidence: 99%

Oxidation of Raloxifene to Quinoids: Potential Toxic Pathways via a Diquinone Methide and o-Quinones

Liu

et al. 2004

Chem. Res. Toxicol.

134

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Raloxifene was approved in 1997 by the FDA for the treatment of osteoporosis in postmenopausal women, and it is currently in clinical trials for the chemoprevention of breast cancer. Before widespread use as a chemopreventive agent in healthy women, the potential cytotoxic mechanisms of raloxifene should be investigated. In the current study, raloxifene was incubated with GSH and either rat or human liver microsomes, and the metabolites and GSH conjugates were characterized using liquid chromatography-tandem mass spectrometry. Raloxifene was converted to raloxifene diquinone methide GSH conjugates, raloxifene o-quinone GSH conjugates, and raloxifene catechols. For comparison, three raloxifene catechols were synthesized and characterized. In particular, 7-hydroxyraloxifene was found to oxidize to the 6,7-o-quinone. As compared with raloxifene diquinone methide, which has a half-life of less than 1 s in phosphate buffer, the half-life of raloxifene 6,7-o-quinone was much longer at t 1/2 ) 69 ( 2.5 min. The stability offered by raloxifene 6,7-o-quinone implies that it may be more toxic than raloxifene diquinone methide. Cytotoxicity studies in the human breast cancer cell lines S30 and MDA-MB-231 showed that 7-hydroxyraloxifene was more toxic than raloxifene in both cell lines. These results suggest that raloxifene could be metabolized to electrophilic and redox active quinoids, which have the potential to cause toxicity in vivo.

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Section: Discussionmentioning

confidence: 99%

Oxidation of Raloxifene to Quinoids: Potential Toxic Pathways via a Diquinone Methide and o-Quinones

Liu

et al. 2004

Chem. Res. Toxicol.

134

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“…It was found that the action of trifluoroacetic acid or polyphosphoric acid on the 2-acyl derivatives of these heterocycles led to intramolecular isomerization to the corresponding 3-isomers and of the 3-alkyl and 3-aryl derivatives to the 2-isomers [75][76][77]. It was found that the action of trifluoroacetic acid or polyphosphoric acid on the 2-acyl derivatives of these heterocycles led to intramolecular isomerization to the corresponding 3-isomers and of the 3-alkyl and 3-aryl derivatives to the 2-isomers [75][76][77].…”

Section: Five-membered Heterocycles With One Heteroatom and Their Conmentioning

confidence: 99%

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Yurovskaya

2005

Chem Heterocycl Compd

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“…1,31–32 The mechanism is widely thought to involve concomitant cyclization and 1,2 aryl ring migration. The regioisomers in this example result from initial cyclization occurring either ortho or para to the methoxy group on the aryl ring of the sulfide.…”

Section: Introductionmentioning

confidence: 99%

“…The regioisomers in this example result from initial cyclization occurring either ortho or para to the methoxy group on the aryl ring of the sulfide. 1,31–32 …”

Section: Introductionmentioning

confidence: 99%

Mechanistic considerations in the synthesis of 2-aryl-indole analogues under Bischler–Mohlau conditions

MacDonough

Shi

Pinney

2015

Tetrahedron Letters

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Mechanistic insight into the pathway of the Bischler-Mohlau indole formation reaction is provided by isotopic labeling utilizing judicious incorporation of a 13C atom within the α-bromoacetophenone analogue reactant. The resulting rearranged 2-aryl indole, isolated as the major product, located the 13C isotope label at the methine carbon of the fused five-membered heterocyclic ring, which suggested that the mechanistic pathway of cyclization, in this specific example, required two equivalents of the aniline analogue reactant partner and proceeded through an imine intermediate rather than by direct formation of the corresponding 3-aryl indole accompanied by a concomitant 1,2-aryl shift rearrangement.

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ChemInform Abstract: ISOMERISIERUNG 3‐SUBSTITUIERTER INDOLE, BENZOFURANE UND BENZOTHIOPHENE

Abstract: Die 3‐Methyl‐ bzw. 3‐Phenyl‐indole, ‐benzofurane und ‐benzothiophene (I) gehen bei 15 ‐420minütiger Erwärmung mit Pyrophosphorsäure auf 100 bis 150°C in die 2‐substituierten Isomeren (IV) (Ausbeute 10‐90%) über.

Cited by 4 publications

References 0 publications

Oxidation of Raloxifene to Quinoids: Potential Toxic Pathways via a Diquinone Methide and o-Quinones

Oxidation of Raloxifene to Quinoids: Potential Toxic Pathways via a Diquinone Methide and o-Quinones

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Mechanistic considerations in the synthesis of 2-aryl-indole analogues under Bischler–Mohlau conditions

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