Highly Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Nitrile Oxides to 2,4‐Dimethyl‐3H‐1,5‐Benzodiazepines: Synthesis of Bis[1,2,4‐Oxadiazolo][1,5]Benzodiazepine Derivatives

Nabih, K.; Baouid, A.; Hasnaoui, A.; Kenz, Ahmed

doi:10.1081/scc-200031020

Cited by 21 publications

(4 citation statements)

References 14 publications

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“…In this way, oxadiazolo-1,4-diazepines, 233 [238], oxadiazole-1,5-benzodiazepines 234 [239], and oxadiazolotriazole-1,5-benzodiazepines 235 have been prepared [240] (Scheme 13.82).…”

Section: 24-oxadiazoles J1101mentioning

confidence: 99%

Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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“…In this way, oxadiazolo-1,4-diazepines, 233 [238], oxadiazole-1,5-benzodiazepines 234 [239], and oxadiazolotriazole-1,5-benzodiazepines 235 have been prepared [240] (Scheme 13.82).…”

Section: 24-oxadiazoles J1101mentioning

confidence: 99%

Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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“…Moreover, DZPs are widely used as synthons for the synthesis of triazole and oxadiazole derivatives. [14][15][16] In the last years, the dependence on the stereochemistry of the seven-membered DZP ring derivatives with biological activity have attracted remarkable interest. [17] The different tautomeric forms of 1,4-DZPs were studied by different experimental techniques such as X-ray diffraction (XRD), nuclear magnetic resonance (NMR), UV-visible spectroscopy, and theoretical calculations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes

et al. 2020

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A new series of CuII, NiII, CoII, and MnIII complexes have been synthesised from the (6Z)-6-(7-trifluoromethyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-ylidene)cyclohexa-2,4-dien-1-one (HDZP) ligand. These complexes were characterised by elemental, spectroscopic (IR and UV-vis), and thermal analysis. The crystal structure of Cu-DZP was solved by X-ray diffraction methods. The complex crystallises in the monoclinic P21/c space group, with two molecules per unit cell. The crystal lattice is stabilised by different intra and intermolecular interactions. Hirshfeld surface analysis was employed to obtain additional information about interactions that are responsible for the crystal packing. Quantitative examination of the fingerprint plots indicated the dominant contribution of H⋯H and H⋯X (X=O, F) interactions in the crystal packing. In addition, C–H⋯chelate ring (CR) and C–H⋯π interactions are described in detail and evaluated using DFT calculations. The antibacterial properties and the mechanism of inhibition of the main bacterial resistant mechanism, the biofilm, of the metal complexes and free ligand were investigated. [Mn(DZP)3]·2H2O was the most active complex against the Pseudomonas aeruginosa biofilm formation with an inhibition of 40%. However, none of the complexes inhibit more than 25% of the Gram negative bacteria microbial development. The most meaningful result was the bactericidal effect of [Co(DZP)2(H2O)2]·2H2O against the Gram positive bacteria, Staphylococcus aureus, which inhibits the bacterial development and significantly reduces the biofilm formation at low concentration.

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“…In the last decade, the area of biological interest of 1,5 and 1,4‐benzodiazepines has been extended to several diseases such as cancer, viral infection, and cardiovascular disorders . In addition,1,4‐benzodiazepines are key intermediates for the synthesis of various fused ring systems such astriazolo‐, oxadiazolo‐, oxazino‐ or furanobenzodiazepines . Besides, 1,4‐benzodiazepine derivatives are also of commercial importance as dyes for acrylic fibers in photography .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Characterization of 1, 3‐disubstituted‐1,4‐benzodiazepine Derivatives

Ghelani

Naliapara

2015

Journal of Heterocyclic Chem

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The 2‐amino‐4′‐flouro‐benzophenone (1) that was reacted with chloroacetylchloride to afford 2‐chloro‐N‐(2‐(4′‐fluorobenzoyl) phenyl)acetamide (2) was subsequently converted to 1,4‐benzodiazepines (3) by the modification of the known hexamethylenetetramine based cyclization reaction developed by Blazevic and Kajfez. Thus, obtained product (3) was reacted with a variety of alkyl halide using KOH in DMF to give 1‐substituted‐5‐(4‐fluorophenyl)‐1H‐benzo[e][1,4]diazepin‐2(3H)‐one (4a, 4b). To achieve 1, 3‐disubstituted 1, 4‐benzodiazepines (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, 5p, 5q, 5r, 5s, 5t), 1‐substituted‐5‐(4‐fluorophenyl)‐1H‐benzo[e][1,4]diazepin‐2(3H)‐one (4a, 4b) was treated with various aromatic aldehydes in the presence of KOH in toluene.

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Highly Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Nitrile Oxides to 2,4‐Dimethyl‐3H‐1,5‐Benzodiazepines: Synthesis of Bis[1,2,4‐Oxadiazolo][1,5]Benzodiazepine Derivatives

Cited by 21 publications

References 14 publications

Oxadiazoles

Oxadiazoles

Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes

Design, Synthesis, and Characterization of 1, 3‐disubstituted‐1,4‐benzodiazepine Derivatives

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