Synthesis, characterisation, stereochemistry and antimicrobial activity of N 5-piperazino- and N 5-morpholinoacetyl-2,2,4-trimethyl-1, 5-benzodiazepines

Abstract

Three 1,5-benzodiazepines viz., N 5-chloroacetyl-, N 5-piperazinoacetyl-and N 5-morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepines have been synthesized. The structural characterisation and the conformational preferences of the compounds have been carried out using IR, 1D and 2D NMR spectral data. The NMR spectral data show that the N-acetyltetrahydro-1,5-benzodiazepines prefer to exist in boat conformation with exo orientation of >C=OatN 5 position in the solution state. The X-ray crystal structure of N 5morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepine also supports boat conformation in the solid state. The antimicrobial activity for N-acetyltetrahydro-1,5-benzodiazepines have been carried out. N-morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepine demonstrated better antibacterial and antifungal activities.

The complete 1H and 13C NMR spectra assignments of N‐(2‐nitrobenzoyl)‐1,5‐benzodiazepin‐2‐one and dihydroquinazolino[3,2‐α]benzodiazepine derivatives

“…The bulk of the reported NMR spectral data for these compounds have been found in publications devoted to the synthesis and research into their biological properties. However, reports of full structural characterization by NMR have been rare . Nevertheless, a few publications with the complete NMR spectra assignments for this class of compounds were noted …”

Highly diastereoselective synthesis of rigid 3-enamino-1,5-benzodiazepines

“…They have been repeatedly reported to possess different clinical uses as anticonvulsant, anxiolytic and sedative agents. 2 More recently, different studies have shown new important biological properties of these compounds such as anti-HIV, anti-neuroinflammatory, 3 antioxidant, 4 antimicrobial, 5 and antitumor, 6 which have led to considerable interest in their synthesis and biological study. These biological properties are correlated with the benzodiazepine structural changes in particular by introduction of a stereogenic unit at C-3 of the benzodiazepine core.…”

Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent

“…Thus, development of new types of antibacterial agents or enhancement of the activity of existing drugs is an urgent need in combating such pathogenic strains. Researchers throughout the world are engaged to develop potential antimicrobial lead compounds via chemical synthesis [7][8][9][10][11][12][13][14][15][16] as well as via the structural modulation of plant secondary metabolites [17][18][19][20]. It is well established that natural products, particularly heterocyclic compounds viz.…”