NEW N-BENZYLPIPERIDONE DERIVATIVES: SYNTHESIS AND PLANT GROWTH-STIMULATING ACTIVITY

Abstract

Introduction. Nitrogen-containing heterocycles are of significant importance due to their prevalence in nature and their role as scaffolds for numerous pharmacologically active compounds. Piperidine derivatives, especially N-benzylpiperidones, exhibit broad pharmacological potential and represent promising candidates for further chemical modification. The appeal of these compounds stems from the availability of starting materials and straightforward synthetic procedures, which facilitate the development of novel compounds with specific physicochemical and biological properties. The objective of this study is to synthesize a new series of benzylpiperidone derivatives, generate more complex nitrogen-containing heterocycles through structural modification, and evaluate their plant growth-stimulating activity. Results and discussion. N-benzylpiperidin-4-one was reacted with 1-(3-methoxypropyl)amine and paraformaldehyde to yield 3-benzyl-7-(3-methoxypropyl)-3,7-diazabicyclo[3.3.1]nonan-9-one. The resulting ketone was converted to the corresponding oxime with a 76% yield under oximation conditions. Subsequent acylation of the oxime with benzoyl chloride produced O-benzoyloxime in 65% yield. The resulting complex (KhZR-107) was assessed for its effects on the germination, growth, and development of wheat (variety Kazakhstan-10) and soybean (variety Zhansaya) seedlings at a concentration of 0.001%. Conclusion. The complex KhZR-107 exhibited a positive influence on wheat seed germination and seedling development. Further investigation under controlled and field conditions is warranted to assess its efficacy and microbiological stability.