Heterocyclische Verbindungen, II. Spektroskopische Konstitutions‐ und Konformations‐bestimmung am 5‐Äthyl‐1‐(3,4‐dimethoxyphenyl)‐7,8‐dimethoxy‐4‐methyl‐5<i>H</i>‐2,3‐benzodiazepin

Neszmélyi, András; Gács‐Baitz, Eszter; Horváth, Gyula; Láng, Tibor; Kőrösi, Jenő

doi:10.1002/cber.19741071220

Cited by 23 publications

(2 citation statements)

References 22 publications

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“…To our delight, a desired substitution reaction took place to afford Tofisopam ( 1 a ) in 60 % isolated yield (Scheme ). The structure of the obtained material was confirmed by comparison of its spectral data (IR and NMR) and melting‐point with those reported in literatures (See Supporting Information).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Tofisopam by Way of Photoinduced CO₂ Fixation

Masuda

Makita

Ishida

et al. 2019

Chemistry An Asian Journal

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Herein reported is a unique synthetic route of Tofisopam, an anxiolytic drug containing a 2,3‐benzodiazepine core structure. 3,4‐Dimethoxypropylbenzene and 3,4‐dimethoxybenzoic acid, which are both of plant origin, and CO2 constitute its carbon skeleton. These three renewable substances are united by two C−C bond forming reactions, i.e., a Friedel–Crafts acylation reaction and a photoinduced carboxylation reaction to construct the major carbon framework. Finally, a methyl group is introduced by a Kumada‐type cross‐coupling reaction to furnish Tofisopam. Various analogs of Tofisopam are readily synthesized by introducing other substituents than a methyl group at the last C−C bond forming step.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Tofisopam by Way of Photoinduced CO₂ Fixation

Masuda

Makita

Ishida

et al. 2019

Chemistry An Asian Journal

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“…1), the first 2,3-benzodiazepine derivative reported in literature, was synthesized in 1966 [28] but its correct structure was assigned only in 1974 [29,30]. This compound was introduced into therapy as a psychovegetative regulator in 1975 [31].…”

Section: Synthesis Of 1-aryl-5h-23-benzodiazepinesmentioning

confidence: 99%

synthesis and Structure-Activity Relationships of 2,3-Benzodiazepines as AMPA Receptor Antagonists

Zappalà

Grasso²,

Micale³

et al. 2001

MRMC

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There is increasing evidence of the potential therapeutic utility of glutamate receptor antagonists in the treatment of several neurodegenerative disorders, including stroke and epilepsy. In the last few years noncompetitive AMPA receptor antagonists have received considerable attention due to their therapeutic potentiality. The discovery of GYKI 52466, the prototype of noncompetitive AMPA receptor antagonists endowed with anticonvulsant and neuroprotective properties, induced growing interest on 2,3-benzodiazepine derivatives. This review covers the chemistry and pharmacology of this important class of AMPA receptor antagonists.

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