Synthesis of novel furo, thieno, and benzazetoazepines and evaluation of their cytotoxicity

Martinez, L.; Zarraga, Jose Gustavo Avila; Duran, Ma Esther; Apam, M. Teresa Ramirez; Cañas, Roberto

doi:10.1016/s0960-894x(02)00232-9

Cited by 18 publications

(7 citation statements)

References 6 publications

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“…5-Methoxy-1-tetralone oxime 12 in polyphosphoric acid gave the aryl-migration lactam 22; no alkyl-migration lactam 17 was observed. This confirmed results reported in the majority of the literature, [41,42] yet disputes the claim made by Martinez et al [43] that the alkyl migration should predominate. In contrast, the Beckmann rearrangement of 12 in thionyl chloride gave mostly the alkyl-migration product 17.…”

Section: Resultssupporting

confidence: 88%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4.

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Section: Resultssupporting

confidence: 88%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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“…However, the effects shown by the different concentrations of 1 tested were not significantly different; the same was true for 2 and 4. These results indicated a constant production of Martı´nez et al (2002). NO, at least for 1, 2 and 4 at the concentrations tested.…”

Section: No Production In Peritoneal Macrophagessupporting

confidence: 51%

Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes

Chávez

Apan

Martínez‐Vázquez³

2005

Journal of Pharmacy and Pharmacology

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Hexane extract from the bark of Amphipterygium adstringens, as well as its principal constituents, masticadienonic acid and 3alpha-hydroxymasticadienolic acid, inhibited the growth of five human cancer cell lines. Derivatives of, namely 24,25 S-dihydromasticadienonic acid and masticadienolic acid, were also evaluated. The results showed that both and had greater activity than on colon cancer cell lines. The effects of on the production of nitric oxide (NO) from both resting and lipopolysaccharide-activated macrophages were determined. It was found that and caused an increase in NO release from resting macrophages; in lipopolysaccharide-activated macrophages, only and caused an increase in NO production.

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“…The results from the screening are shown in Table . The Paal–Knorr thiophene synthesis of 19 using Lawesson’s reagent (LR) in THF yielded both 21 and 22 in a 7.4:1 ratio (Table , entry 1), which agrees with the study of Minetto et al Notably, changing LR to other sulfating reagents, i.e., Davy reagent or P 4 S 10 (Table , entries 2 and 3, respectively), did not improve the ratio. In contrast, diluting the concentration of 19 in the reaction mixture and increasing the reaction temperature were effective (Table , entries 1, 4, and 5).…”

Section: Resultssupporting

confidence: 86%

“…The Paal–Knorr thiophene synthesis is a valuable synthetic method for the production of substituted thiophenes, although its application to large-scale preparation is challenging. A furanyl byproduct was reported to be generated along with the desired thiophene product in this reaction . Therefore, the reaction conditions were first optimized to suppress the formation of furanyl byproduct 22 .…”

Section: Resultsmentioning

confidence: 99%

Efficient and Scalable Synthesis of Glucokinase Activator with a Chiral Thiophenyl-Pyrrolidine Scaffold

Fujieda

Maeda

Kato

2018

Org. Process Res. Dev.

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Herein we describe the practical synthesis of a potent glucokinase activator (1) that has a chiral thiophenylpyrrolidine scaffold. The key to the successful synthesis was the application of a telescoped chiral-pool synthesis from a commercially available L-proline methyl ester derivative to introduce the chirality of the thiophenyl-pyrrolidine moiety. This second-generation synthesis of 1 provided several advantages over the previous method including an operational simplicity and avoidance of purification by column chromatography. The industrial relevance of this synthetic method in large-scale preparation was demonstrated by the production of 54.6 kg of 1 with an excellent chemical and optical purity.

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Synthesis of novel furo, thieno, and benzazetoazepines and evaluation of their cytotoxicity

Cited by 18 publications

References 6 publications

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes

Efficient and Scalable Synthesis of Glucokinase Activator with a Chiral Thiophenyl-Pyrrolidine Scaffold

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