Abstract
Objective: Derivatives of 3,7-diazabicyclo[3.3.1]nonan-9-one attract considerable attention from pharmacists for the treatment of a wide rangeof diseases. According to this interest, the novel derivatives of 3-cyclopropanmethyl-7-alkoxyalkyl-3,7-diazabicyclo[3.3.1]nonan-9-one withisopropoxypropyl and ethoxypropyl substituents in the position 7 had been synthesized to study their biological activity and toxicity. The practicalsignificance of the work is in the accumulation and development of scientific representations about diazabicyclic compounds, methods for theirsynthesis, structure, and properties, which can subsequently be used in a targeted design and identification of even more complex systems, as wellas in the development of further research in the field of 3,7-diazabicyclo[3.3.1]nonanes. For this purpose, complexes of the synthesized compoundswith β-cyclodextrin are obtained and their biological activity is investigated at the Department of Pharmacology of S.D. Asfendiyarov Kazakh NationalMedical University with the aid of the pharmacological tests.Methods: An experimental study of local anesthetic activity on the models of infiltration, conduction anesthesia, and acute toxicity of synthesizedmolecules was carried out using primary screening methods.Results: As a result of pharmacological screening, it has been found that the compounds exhibit local anesthetic activity and low toxicity and wasrecommended for in-depth study of their pharmacological properties.Conclusion: It turned out that a nature of the N-alkoxyalkyl radical does not affect the toxicity of cyclopropanmethyl- substituted bispidines. In theseries of O-benzoyloximes of bispidinones, the isopropoxypropyl- substituted analog is 1.3 times less toxic than ethoxypropyl- one.
Highlights
An analysis of current trends in the medical use of drugs indicates the ongoing gradual replacement of obsolete drugs with more effective and safe drugs of novel generations
As a result of pharmacological screening, it has been found that the compounds exhibit local anesthetic activity and low toxicity and was recommended for in-depth study of their pharmacological properties
It turned out that a nature of the N-alkoxyalkyl radical does not affect the toxicity of cyclopropanmethyl- substituted bispidines
Summary
An analysis of current trends in the medical use of drugs indicates the ongoing gradual replacement of obsolete drugs with more effective and safe drugs of novel generations. Research on the search for novel potentially biologically active substances is relevant. The aim of research is the synthesis of novel potentially pharmacologically active derivatives of 3-cyclopropanmethyl-7alkoxyalkyl-3,7-diazabicyclo[3.3.1]nonan-9-one, as well as the establishment of the structure and evaluation of their biological activity. The interest of chemists in the study of heteroanalogs of bicyclo[3.3.1] nonane is due to the unique properties of these compounds, which makes them valuable from a theoretical and practical point of view [1-10]. It is known that methylenecyclopropane residue is a valuable structural unit of bioactive compounds, opiate antagonists [11,12]. 1-(3-Isopropoxypropyl- and 3-ethoxypropyl-)-4-oxopiperidine (1, 2) as starting substrates was used to obtain the target bispidines (3-14) according to Fig. 1. The reaction products were obtained with high yields as viscous oils. Monitoring of the progress of the reaction was carried out by TLC on alumina. The structure of bispidinone derivatives (3-10) was determined by nuclear magnetic resonance (NMR) and infrared (IR) spectroscopies
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