Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety

Abstract

Acylation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo [4,3-d) pyrimidin-7-one 1 with chloroacetylchloride in the presence of anyhydrous aluminium chloride affords 5-[(5-chloroacetyl-2-ethoxy)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one 2. The compound 2 condensed with various β-diketones/β-ketoesters compound, to obtain new β-diketones/ β-ketoesters 4a-i treated with ethylenediamine (EDA) gives 1H-1,4-diazepines. The compounds 5a-i has been screened for antimicrobial, antifungal and anthelmintic activities.

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“…TLC was used to monitor the completion of the reaction; the structures of products were assessed by interpretation of IR and NMR spectra obtained. The spectroscopic data of IR and 1 H-NMR are in agreement with the structure of fused 1, 4-diazepine derivatives 3,4,6,7,8,9,10 .…”

“…Besides being core unit of commercial drugs such as Diazepam, Oxazepam, Laurazepam, Anthramycin & Mazhethramycin; there are numerous Diazepines that are described with antiinflammatory, anticancer, anti-HIV, antibacterial, herbicidal and PAF receptor antagonist activities 1,2,3 . Investigators are motivated to continuously develop strategies for producing new diazepine-based compounds due to the surprisingly vast biological activities exhibited by diazepines 1 .…”

Triethylamine‐Catalyzed Synthesis of Oxazepine from Maleamic Acids

“…Seven‐membered ring systems containing two heteroatoms oxazepines (N and O) and their aryl‐annelated (benzoxazepines) and structural analogues diazepines (N and N) and thiazepines (N and S) occupy an important place in the realm of synthetic organic chemistry, as they account for a significant portion of widely prescribed azepine‐based drugs possessing/showing manifold biological activities like antidepressant , anticonvulsant , antiviral , antimicrobial , antifungal , anticancer , antithrombotic , antihistamines , nonnarcotic analgesic , sedatives, and hypnotics . They are also active in the treatment of Alzheimer's disease and type 2 diabetes .…”

Antimycobacterial Activity of Pyrimido[4,5‐b]diazepine Derivatives

“…In addition, new drugs are needed to combat the increasing number of multidrug‐resistant strains (MDR‐TB) and extensively drug‐resistant (XDR‐TB) strains and HIV epidemics, leading to an increased need to understand the molecular mechanisms of drug action and drug resistance, which should provide significant insights into the development of new compounds 2. In this effort, diazepine derivatives are scaffolds that have shown a broad spectrum of biological activities as anticancer, antibacterial, psychotropic, anticonvulsant, antiviral, and herbicidal agents; these facts present them as a promising source of new compound leaders 3. Benzodiazepines are an important class of psychotherapeutic compounds.…”