Diazepine Derivatives Research Articles

ChemInform Abstract: AuCu and AgCu Bimetallic Nanoparticles Supported on Guanidine‐Modified Reduced Graphene Oxide Nanosheets as Catalysts in the Reduction of Nitroarenes: Tandem Synthesis of Benzo[b][1,4]diazepine Derivatives.

AbstractAuCu and AgCu bimetallic nanoparticles supported on guanidine‐grafted reduced graphene oxide nanosheets are synthesized and utilized as catalysts in the reduction of nitroarenes and the tandem synthesis of the title diazepine derivatives.

ChemInform Abstract: A Serendipitous Synthesis of 11a‐Hydroxy‐11,11a‐dihydrobenzo[e]indeno[2,1‐b] [1,4]diazepine‐10,12‐dione Derivatives by Condensation of 2‐Aminobenzamides with Ninhydrin in Water.

AbstractNinhydrin undergoes an unprecedented condensation reaction with benzamides (I) to give novel diazepine derivatives.

Synthesis, characterization and photophysical properties of novel 5,7-disubstituted-1,4-diazepine-2,3-dicarbonitriles

Three 5,7-disubstituted-1,4-diazepine-2,3-dicarbonitriles with bulky 2-(3,5-dibromophenyl)ethenyl, 2-(4-tert-butylphenyl)ethenyl and 2-(3,5-dibenzyloxyphenyl)ethenyl substituents were synthesized and characterized using UV–Vis, MS ES, elemental analysis and NMR spectroscopy. NMR data indicated that diazepine rings of all obtained compounds adopted 6H-tautomeric form. In addition, trans-isomerism within styryl substituents was observed. Experimental data for diazepine derivative containing 2-(4-tert-butylphenyl)ethenyl substituents were verified by X-ray crystallography. The obtained compounds were subjected to photophysical studies. In the UV–Vis absorption spectra two characteristic bands were found. In the solvatochromic study, the first band maxima were located in the range of 384–418 nm, whereas second band maxima in the range of 313–345 nm. Fluorescence intensity of novel diazepine derivatives was rather low in all solvents used with the values of fluorescence quantum yield ФF=10−4 for 2-(3,5-dibromophenyl)ethenyl, and 10−5 for 2-(4-tert-butylphenyl)ethenyl and 3,5-(dibenzyloxyphenyl)ethenyl 1,4-diazepine-2,3-dicarbonitriles.

Skeletally Diverse Synthesis of Indole-Fused Diazocine and Diazepine Frameworks by One-Pot, Two-Component Cascade Reaction.

An expeditious and novel strategy has been explored for the synthesis of structurally diverse indole-fused diazocine and diazepine derivatives. A substrate-based diversification approach of methyl-3-aminoindole/indoline benzoates coupled with the Pictet-Spengler reaction and three different reaction cascades furnished indolodiazepine and indoloquinoxalines. The formation of indolodiazocines proceeds through an initial condensation followed by intramolecular alkylation.

Design, Synthesis and Structure-Activity Relationship Study of Pyri-midine-Fused Diazepine Derivatives as L3MBTL3 Inhibitors

Design, Synthesis and Structure-Activity Relationship Study of Pyri-midine-Fused Diazepine Derivatives as L3MBTL3 Inhibitors

AuCu and AgCu bimetallic nanoparticles supported on guanidine-modified reduced graphene oxide nanosheets as catalysts in the reduction of nitroarenes: tandem synthesis of benzo[b][1,4]diazepine derivatives

AuCu and AgCu bimetallic nanoparticles supported on guanidine-grafted reduced graphene oxide nanosheets as reduction catalysts.

Synthesis, Characterization and Biological Evaluation of Benzo[b][1, 2, 4]triazolo [4, 3-d][1, 4]diazepine Derivatives

Heterocyclic compounds occur widely in nature and quite a few of these are essential to life processes. The literature on heterocyclic compounds is replete with examples of a large number of synthetic methods of naturally occurring systems which are pharmacologically active. The heterocyclic compounds containing nitrogen has expanded exponentially in the past decades due to their unique physical properties, specific chemical reactivity and their remarkable potential biological activities. A survey of literature on the nitrogen heterocyclic reveal that dia zepines are important constituents of a wide variety of natural products with pharmacodynamic application. The Structures of the Synthesized Compounds are Confirmed by IR, 1H NMR and 13C NMR Spectral data, Elemental Analysis, Mass spectral data. The compounds are also evaluated for their anti Oxidant activity by DPPH method, among them 13e and 13d are found as potent activity. The reaction proceeds efficiently under ambient conditions with good-to-excellent yields.

Chemistry of 1,5-diketones: V. Hydrazination of acyclic and heterocyclic (poly)carbonyl compounds

Reactions of 2-(1-aryl-3-oxo-3-phenylpropylidene)-3,4-dihydronaphthalen-1(2H)-ones, 3-(1-aryl-3-oxo-3-phenylpropyl)-3,4-dihydro-2H-chromene-2,4-diones, and 3,3'-(arylmethylene)bis(3,4-dihydro-2H-chromene-2,4-diones) with hydrazine hydrate have been studied. Depending on the substrate structure, these reactions involve intramolecular heterocyclization with participation of the exocyclic double bond and sidechain carbonyl group or both oxo groups to give new pyrazole, indazole, and diazepine derivatives, as well as hydrazones.

ChemInform Abstract: Phosphine‐Catalyzed [4 + 3] Cycloaddition Reaction of Aromatic Azomethine Imines with Allenoates.

AbstractAn efficient access to a variety of highly valuable diazepine derivatives annulated with an isoquinoline, quinoline, or phenanthridine skeleton is developed.

CuI nanoparticles as a remarkable catalyst in the synthesis of benzo[b][1,5]diazepines: an eco-friendly approach.

Highly efficient CuI nanoparticles catalyzed one-pot synthesis of some benzo[b][1,5]diazepine derivatives via multi-component condensation of aromatic diamines, Meldrum's acid and isocyanides. The present approach creates a variety of benzo[b][1,5]diazepines as pharmaceutical and biologically active heterocyclic compounds in excellent yields and short reaction times. The salient features of the copper iodide nanoparticles are: easy preparation, cost-effective, high stability, low loading and reusability of the catalyst. The prepared copper iodide nanoparticles were fully characterized by XRD, EDX, FT-IR, SEM and TEM analysis.

An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents

A new series of chalcones 5a–f were synthesized from caffeine-based aldehyde 3 and substituted acetophenones 4a–f. Treatment of compounds 5a–f with hydrazine hydrate led to pyrazolines 6a–f, and their subsequent reaction with acetic anhydride or formic acid afforded the corresponding N-substituted pyrazolines 7a–f and 8a–f respectively. Additionally, the regioselective cyclocondensation reaction of chalcones 5a–f with 4,5-diaminopyrazole 9 afforded the diazepine derivatives 10a–f. Synthesis of the above novel compounds was carried out through a simple procedure involving an easy work-up and mild reaction conditions. In vitro antimalarial activity against Plasmodium falciparum was evaluated for the obtained compounds. Among of them, just pirazoline 6a showed an outstanding growth inhibition percentage 85.2 ± 5.4%, while diazepines 10a–f showed remarkable growth inhibitions in the range of 80.3 ± 13.5 to 94.2 ± 0.2% when were tested at 20 μg/mL. Compounds 5b, 5e, 7c and 7f showed remarkable activities against Leishmania panamensis with growth inhibition of 88.3 ± 1.5, 82.6 ± 2.2, 82.8 ± 1.7 and 87.6 ± 0.5% respectively, at 20 μg/mL. In vitro assays against Trypanozoma cruzi showed that pyrazoline 6d displayed a growth inhibition of 61.9 ± 7.8% at 20 μg/mL while chalcone 5f was considered especially active with a growth inhibition of 9.7 ± 1.5% for a very low concentration of 1.0 μg/mL.

Copper-Bronze Catalyst: An Efficient Green Approach for the Synthesis of Dibenzo[b,e][1,4]diazepine Derivatives

Dibenzo(b,e)(1,4)diazepine derivatives medicinally important hetero systems have been synthesized by green, efficient and convenient synthesis involving Cu-bronze as a novel catalyst by condensation of o-phenylenediamine with aromatic aldehydes. This method is advantageous because of high yield of product easy workup procedure. The synthesized compounds were characterized by 1 H NMR, Mass and IR spectral analysis.

Diazepine Derivative Compounds as Heat Shock Protein 90 Inhibitor in Oncology

Diazepine Derivative Compounds as Heat Shock Protein 90 Inhibitor in Oncology

Synthesis and biological evaluation of novel chiral diazepine derivatives as bombesin receptor subtype-3 (BRS-3) agonists incorporating an antedrug approach

Novel compounds based on the lead BRS-3 agonists from our HTS compounds 2a and 2b have been synthesized with the focus on obtaining peripheral BRS-3 agonists. To identify potent anti-obesity compounds without adverse effects on the central nerve system, a labile carboxylic ester with an antedrug functionality was introduced onto the terminal position. Through the extensive synthetic exploration and the pharmacokinetic studies of oral administration in mice, the phenol ester 17c was selected due to the most suitable pharmacological profile. In the evaluation of food intake suppression in B6 mice, 17c showed significant in vivo efficacy and no clear adverse effect on heart rate and blood pressure change in dog iv infusion. Our study paved the way for development of anti-diabetes and obesity drugs with a safer profile.

Influence of the nature of the substituent on the supramolecular synthon in crystals of benzo[b][1,4]diazepine derivatives

New benzo[b][1,4]diazepine derivatives, which differ only by the substituents in the positions 2 and 4 of the diazepine ring, were synthesized and studied by physicochemical methods. According to the X-ray diffraction data, the benzodiazepine moiety adopts a boat conformation in the crystal. The influence of the nature of the substituents on the type of the resulting supramolecular synthons was investigated.

Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety

Reactions of indole-2,3-dione 1 with 2-mercaptobenzimidazole, o-phenylenediamine, 2-aminophenol, 2-aminobenzothiazole, 2-aminobenzimidazole and 3-methyl-1-phenyl-2-pyrazolin-5-one were carried out to give compounds spiroindolethiazetobenzimidazole 2, spirobenzimidazole(oxazole)indoline 3a,b, benzothiazol(imidazol) iminoindolinone 4a,b and methyloxoindolylidenepyrazolone 5 respectively. Compound 5 was reacted with 2-aminophenol as well as o-phenylenediamine to give new spirooxazepine and diazepine derivatives 6a,b respectively. Reaction of 5 with nitrogen nucleophiles as well as carbon nucleophiles was investigated to furnish new spiro heterocycles 7-11. The reaction of 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile compound 12 with 3-methyl-1-phenyl-2-pyrazoline-5-one was carried out to give spiroindolopyranopyrazolo derivative 13. Compounds 4a,b was reacted with thioglycolic acid to give thiazolidinone derivatives 14a,b. Epoxidation of 5 using monoperoxyphthalic acid magnesium salt hexahydrate and hydrogen peroxide were executed to afford the novel dispiro (2-pyrazolin oxiraneindoline)dione compound 15. The chemical structures of the synthesized compounds were well established by elemental and spectral analyses. Keywords: Spiroheterocycles; Epoxidation; Diazapines, Oxazepines; Spirothiazolidinone. © 2014 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved. doi: http://dx.doi.org/10.3329/jsr.v6i2.17590 J. Sci. Res. 6 (2), 303-317 (2014)

Synthesis of thieno[2,3-e][1,4]diazepine derivatives

Synthesis of thieno[2,3-e][1,4]diazepine derivatives

Synthesis, Pharmacological, and Biological Screening of Novel Derivatives of Benzodiazepines

A series of novel 4‐(substituted phenyl)‐2‐(thiophen‐2‐yl)‐2,3‐dihydro‐1H‐benzo[b][1,4]diazepine have been synthesized from 3‐(substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one. 3‐(Substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one was prepared by condensing 2‐acetyl thiophene with various aromatic aldehydes in the presence of 20% NaOH as base. Different 3‐(substituted phenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one on cyclization with o‐phenylenediamine in the presence of NaOH as base resulted in 4‐(substituted phenyl)‐2‐(thiophen‐2‐yl)‐2,3‐dihydro‐1H‐benzo[b][1,4]diazepine derivatives. The structures of synthesized compounds are confirmed by IR, 1H NMR, mass spectra, and elemental analysis. All the compounds have been screened for their antimicrobial, analgesic, and anti‐inflammatory activities.

Synthesis and Spectral Studies of Novel Diazepine Derivatives and Study in Specific Reference to Tautomerization

Condensation of various 1,3-diketone derivatives (1a-1f ) with ethylene diamine and O-PDA in absolute ethanol led to synthesis of new 1,4-diazepines and 1,5-benzodiazepine derivatives. Structure of newly synthesized 1,4-diazepines ( 2a-2f ) and 1,5-benzodiazepine derivatives ( 3a-3f ) were established on the spectral studies viz : IR, 1 H NMR, 13 C NMR.

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.