A series of novel O-triazolyl-1,5-benzodiazepin-2-ones 6aeo and O-isoxazolyl-1,5benzodiazepin-2-ones 7aeo was synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne eazide coupling reaction of N-substituted-1,5-benzodiazepineealkyne derivatives 3aec with various aromatic azides 4aee and nitrile oxides 5aee, respectively. The chemical structures of synthesized compounds were determined using 1 H NMR, 13 C NMR, heteronuclear multiple bond correlation (HMBC), high-resolution mass spectra, as well as elemental analysis and was further confirmed by an X-ray diffraction analysis for compound 7d.
A variety of new (3-Z)-3-((alkyl/aryl)aminomethylene)-4-(2-hydroxyphenyl)-1,3-dihydro-2H-1,5-benzodiazepin-2-ones were synthesized via addition of primary amines on the benzopyrano[4,3-c]-1H-1,5-benzodizepin-2one. High yields with excellent diastereoselectivity were obtained. The structure of cis-β-enamino-1,5benzodiazepine derivatives was characterized by 1D and 2D NMR and confirmed by an X-Ray diffraction analysis. All prepared compounds were evaluated for their in vitro antibacterial activities and promising results were given.
Diazo compounds derived from aromatic aldehydes were reacted with derivatives of (Z)-2-arylidene-2H-benzofuran-3-ones to give new highly substituted heterocyclic pyrazoles. The structures of the synthesised compounds were determined on the basis of their elemental analyses and spectroscopic data.
Novel 1,2,3-triazolo-linked-1,5-benzodiazepinones were designed and synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC). The chemical structures of these compounds were confirmed by 1H NMR, 13C NMR, HMBC, HRMS, and elemental analysis. The compounds were screened for their in vitro antibacterial and antifungal activities. Several compounds exhibited good to moderate activities compared to those of established standard drugs. Furthermore, the binding interactions of these active analogs were confirmed through molecular docking.
Benzodiazepines are pharmaceutically important synthetic materials. Reaction of the 4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-one with 2-diazopropane (DAP) gave a mixture of the 2-isopropylether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine and 1-isopropyl-4-(2-hydroxyphenyl)-3H-1,5-benzodiazepin-2-one. Whilst diphenyldiazomethane (DPDM) gave 1-benzhydryl-4-(2-hydroxyphenyl)-3H-1,5-benzodiazepin-2-one. Reaction of the corresponding thione with DAP led to the 2-isopropylthioether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine and 1-isopropyl-4-(2-hydroxyphenyl)-1,5-benzodiazepine-2-thione while the reaction with DPDM gave the 2-benzhydrylthioether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine. The characterisation of these prepared - N, - O and - S alkylated benzodiazepines involved 1D and 2D-NMR techniques, mass spectrometry and elemental analysis.
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