Diazepine Derivatives Research Articles

Synthesis of substituted (oxazepine, Diazepine, tetrazde) via Schiff Bases for 2- Aminobenzo Thaizole Derivatives

This work includs synthesis of several Schiff bases by condensation of 6- methoxy – 2- amino benzothiazole with some aldehydes and ketones (2- hydroxyl benzaldehyde, 4- hydroxyl benzaldehyde, 4- N,N –dimethy amino acetophenone, benzophenone) to abtain schiff bases (1-5). These schiff bases were found to react with phthalate anhydride to give oxazepine derivatives (6-10) that were reacted with primary aromatic amines to give Diazepine derivatives (11-15). Besides, we prepared new tetrazole derivatives (16-20) from the reaction of the prepared Schiff bases with sodium azide in the prepared compounds that were characterized by physical properties, FT-IR and some of the 1H-NMR and 13C –NMR spectroscopy.

Facile synthesis and coupling of 3,9-dibromo-6-aryl-5H-dibenzo[d,f][1,3]diazepine derivatives

A route has been developed to prepare 3,9-dibromo-6-aryl-5H-dibenzo[d,f][1,3]diazepine derivatives which undergo facile Suzuki coupling to generate extended conjugated moieties bearing this unit. Single crystal X-ray studies on three of the coupled products provide valuable information on the conformation and bulk packing of these materials.

ChemInform Abstract: One‐Pot Multicomponent Synthesis of Diazepine Derivatives Using Terminal Alkynes in the Presence of Silica‐Supported Superparamagnetic Iron Oxide Nanoparticles.

AbstractThe synthesis of a magnetically recoverable Fe3O4 material is described.

One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles

A new, efficient, one-pot multicomponent reaction for the synthesis of diazepine derivatives in excellent yields is described. The reactions of various 1,2-diamines, terminal alkynes, and an isocyanide take place in the presence of a catalytic amount of magnetically recoverable silica-supported superparamagnetic Fe3O4 nanoparticles in ethanol (as a green reaction medium) at ambient temperature.

ChemInform Abstract: Fe3O4/SiO2 Nanoparticles: An Efficient and Magnetically Recoverable Nanocatalyst for the One‐Pot Multicomponent Synthesis of Diazepines.

AbstractThe present new one‐pot multicomponent reaction of a diamine, a linear or cyclic ketone, and an isocyanide proceeds in the presence of a silica‐supported iron oxide catalyst affording diazepine derivatives in high yields.

Expeditious synthetic approach and photophysical properties of fluorescent benzimidazo[1,2-d]dibenzo[b,f][1,4]diazepine derivatives

A short and efficient synthetic route to novel benzimidazo[1,2-d]dibenzo[b,f][1,4]diazepines has been developed using a copper catalyzed intramolecular Ullmann type C–N bond forming reaction as a key step. Copper iodide and 1,10-phenanthroline furnished the desired compounds in good yield. The products are intensely fluorescent with appreciably long lifetimes. Looking at their prospective use as markers for biomacromolecules and in biochemical analysis, we have explored the photophysical properties of these compounds. The spectrophotometric and spectrofluorometric studies reveal that while the absorbance maxima of the compounds are in the UV region, the emission maxima fall in the visible (blue-green) region.

ChemInform Abstract: Synthesis of New Di‐, Tetra‐, and Hexahydropyrazolo[3,4‐e][1,4]diazepine Derivatives.

AbstractAn efficient procedure for the synthesis of N‐substituted 5‐aminopyrazole‐4‐carboxamides capable to suffer intramolecular diazepine ring closure is given.

Exploration of Newer Possibilities to the Synthesis of Diazepine and Quinoline Carboxylic Acid Derivatives

Heterocyclic systems containing benzothiazoles, carbazole (and azacarbazole) moieties have attracted the attention of chemists owing to these nuclei having been identified in the literature as most promising pharmacophores in drug design and synthesis. Based on these observations, it could be anticipated that incorporation of the bioactive azepine moiety and quinoline moiety into the molecular framework of benzothiazoles fused to carbazole (and azacarbazoles) could produce interesting series of compounds 9–12 with enhanced biological activities, whose structure was unequivocally established from its microanalyses and spectral data.

Fe3O4/SiO2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines

In this research, a new protocol for the one-pot multicomponent synthesis of diazepine derivatives using a 1,2-diamine, a linear or cyclic ketone, and an isocyanide in the presence of a catalytic amount of silica-supported iron oxide (Fe3O4/SiO2) nanoparticles at ambient temperature in excellent yields is described.

A novel one-pot pseudo-five-component condensation reaction towards bifunctional diazepine-tetrazole containing compounds: synthesis of 1H-tetrazolyl-1H-1,4-diazepine-2,3-dicarbonitriles and 1H-tetrazolyl-benzo[b][1,4]diazepines

A novel and efficient method has been developed for the one-pot synthesis of bifunctional diazepine-tetrazole containing compounds. 1H-Tetrazolyl-1H-1,4-diazepine-2, 3-dicarbonitrile and 1H-tetrazolyl-benzo[b][1,4]diazepine derivatives were synthesized in good yields using 2,3-diaminomaleonitrile or an aromatic diamine, ketones, trimethylsilyl azide, and an isocyanide in the presence of p-toluenesulfonic acid as a catalyst in methanol at room temperature.

Synthesis and electrochemical evaluation of substituted imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine scaffolds

Substituted 4-(2,5-dihydro-1H-pyrrol-3-yl)-1H-imidazoles were prepared from 5-amino-1-aryl-4-cyanoformimidoylimidazoles and cyanoacetamide, under mild experimental conditions. The pyrrolyl-imidazoles were cyclized to the corresponding 7,8-dihydroimidazo[4,5-b]pyrrolo[3,4-d]pyridines by reflux in ethanol, with catalysis by DBU. The same pyrrolyl-imidazoles were reacted with orthoesters, at room temperature and in the presence of sulfuric acid, to generate 3,7-dihydro-8H-imidazo[4,5-d]pyrrolo[3,2-f]diazepines in very good yield. Electrochemical studies of the imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine derivatives were carried out. The reduction potential of 7-ethyl-3-(4-methoxyphenyl)-8-oxo-7,8-dihydro-3H-imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine-9-carbonitrile was in the adequate range for presenting bioreduction properties.

Design, synthesis and biological evaluation of new molecules inhibiting epidermal growth factor receptor threonine790→ methionine790 mutant

A series of 5,8-dioxo-pyrimido[4,5-e][1,4]diazepine derivatives were designed and synthesized as new inhibitors against wild-type EGFR and a panel of mutants, including the clinical resistance related T790M mutants. One of the most potent compounds 2l inhibited all forms of EGFR evaluated with low nM IC50 values. It also strongly suppressed the proliferation of H1975 and HCC827 non-small cell lung cancer cells with IC50 values of 69 and 71 nM, respectively.

ChemInform Abstract: [4 + 2 + 1] Domino Cyclization in Water for Chemo‐ and Regioselective Synthesis of Spiro‐Substituted Benzo[b]furo[3,4‐e][1,4]diazepine Derivatives.

AbstractAll products are purified by being merely filtered and then washed with ethanol.

Synthesis of Dibenzo[b,e][1,4]Diazepine Derivatives

The reaction of ( Z)-2-amino- N‘-arylbenzamidines with both 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 2,3,5,6-tetrachloro-1,4-benzoquinone have been studied. The reactions were carried at room temperature overnight in dry ethyl acetate and proceed via a charge transfer complexe to give dibenzo[ b,e][1,4]diazepine derivatives in 35–44% yield. Benzodiazepine derivatives have anti-inflammatory, antiviral, antimicrobial, antileukaemic, antiplatelet, anticonvulsant, antianxiety, antidepressive and antitumour activities. The products were fully characterised according to their spectral analyses.

An Efficient Three-component Tandem Reaction Leading to Pentacyclic Isoindole-fused Benzo[b,e][1,4]diazepines in Water

Abstract An efficient methodology for the synthesis of highly functionalized pentacyclic isoindole-fused benzo[b,e][1,4]diazepine derivatives from readily available common reactants in water has been developed. The tandem reaction resulted in efficient assembly of two new rings and four σ bonds including three C–N bonds in a one-pot operation.

Solid-phase synthesis of 2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine derivatives

We have developed an efficient solid-phase synthetic approach for the synthesis of 2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine derivatives. The methodology is of value for high throughput synthesis of these potentially bioactive molecules.

4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives

New regio- and chemoselective [4+2+1] domino cyclization consisting of the formation of two spiro rings and five σ bonds has been developed for the synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives. The reaction is a multicomponent domino green process and can be readily performed by reacting inexpensive starting materials of benzene-1,2-diamines, tetronic acid and 2,2-dihydroxy-2H-indene-1,3-dione in aqueous solution under microwave irradiation. The present synthesis shows attractive characteristics, such as the use of water as reaction media, convenient one-pot operation, short reaction periods of 10–18 min and reduced waste production without the use of any strong acids or metal promoters. This synthesis serves as a nice addition to GAP (Group-Assistant-Purification) chemistry in which purificationviachromatography and recrystallization can be avoided, and the pure products were obtained simply by washing the crude products with 95% EtOH.

Interaction of clozapine and its nitrenium ion with rat D2 dopamine receptors: in vitro binding and computational study

The interaction of diazepine analogues like clozapine or olanzapine with D2 receptor was greatly affected by a mixture of HRP/H(2)O(2) known to induce the formation of nitrenium ion. Unlike diazepine derivatives, the oxidative mixture had low impact on the affinity of oxa- and thiazepine derivatives such as loxapine, clothiapine or JL13 for the D2 receptor. Molecular docking simulations revealed a huge difference between the mode of interaction of clozapine nitrenium ion and the parent drug. Electronic and geometric changes of the tricyclic ring system caused by the oxidation appeared to prevent the compound finding the correct binding mode and could therefore explain the difference observed in binding affinities.

ChemInform Abstract: Synthesis of Novel 8,9‐Dihydro‐5H‐pyrimido[4,5‐e][1,4]diazepin‐7(6H)‐ones.

AbstractBis‐electrophilic pyrimidines such as (I), (VII), (X), and (XII) and aliphatic or aromatic amines or ammonia give the title diazepine derivatives bearing a 4‐chloro substituent (25 examples).

ChemInform Abstract: Synthesis and Reactivity of Monothiooxamides of the Aminonitroarenes Series.

AbstractThe synthesis of monothiooxamides containing aminonitrobenzene and aminonitropyridine fragments and their conversion into thioesters, fused imidazole and diazepine derivatives are described.