Novel Complexes of 3-[3-(1H-Imidazol-1-yl)propyl]-3,7-diaza-bispidines and β-Cyclodextrin as Coatings to Protect and Stimulate Sprouting Wheat Seeds

Kaldybayeva A.B. Yu V.K. Malmakova A.E. Li T. Ten A.Y. Seilkhanov T.M. Praliyev K.D. Berlin K.D.
November 2022 MDPI

Molecules
2022 #27 Issue 21

We report the syntheses and characterization of novel 3,7-bicycl[3.3.1]bispidines possessing an imidazolpropyl group attached to N-3, and at N-7 a Boc group, as well as a benzoylated-oximated group at C-9. These compounds were complexed with β-cyclodextrin [β-CD] and evaluated as seed protectors of selected wheat seedlings. Using strong acid, condensations of N-substituted piperidones with the appropriate imidazolpropyl groups at N-3 and N-7 led to bispidinones 6 and 7. These intermediates were reduced to the corresponding 3,7-diazabicyclo[3.3.1]nonane targets. The oxime at C-9 was benzoylated to yield 13. Heating these 3,7-diazabicyclo[3.3.1]nonanes in ethanol with β-CD generated the complexes required. We investigated the ability of such complexes as coatings on seedlings to protect and stimulate growth of three varieties of wheat, namely Kazakhstanskaya-10, Severyanka, and Miras. The complex of 3-[3-(1H-imidazol-1-yl)propyl]-7-(3-methoxypropyl)-3,7-diazabicyclo[3.3.1]nonane (2) promoted growth in the root systems of all three wheat varieties by more than 30% in Kazakhstanskaya-10, 30% in Severyanka and 8.5% in Miras. A complex of 3-Boc-7-[3-(1H-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane (9) increased both shoot and root length in only the Severyanka variety. The complex of 3-(3-butoxypropyl)-7-[3-(1H-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane (11) stimulated both shoot growth (0.8%, 12.3%, 13.5%) and root growth (12.3%, 9.4%, 21.7%) in all three varieties of wheat, respectively. The nature of substituents on the bispidine affect the activity. Solid complexes (1:1) were generated as powders which melted above 240 °C (dec) and were characterized via elemental analyses as 1:1 complexes.

1-[3-(1H-imidazol-1-yl)propyl]piperidine , 3-[3-(1H-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonanes , activity–complex correlations , growth-stimulating activity , β-cyclodextrin

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Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St, Almaty, 050010, Kazakhstan
Department of Chemistry and Technology of Organic Substances, Natural Compounds and Polymers, Al Farabi Kazakh National University, 71 Al-Farabi Ave, Almaty, 050040, Kazakhstan
Laboratory of Cell Engineering, Institute of Plant Biology and Biotechnology, 45, Timiryazev Str., Almaty, 050040, Kazakhstan
Laboratory of the Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau University, 76, Abay St., Kokshetau, 020000, Kazakhstan
Department of Chemistry, Oklahoma State University, Stillwater, 74078, OK, United States

Laboratory of Chemistry of Synthetic and Natural Medicinal Substances
Department of Chemistry and Technology of Organic Substances
Laboratory of Cell Engineering
Laboratory of the Engineering Profile of NMR Spectroscopy
Department of Chemistry

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