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.
Molecules. 2022 Nov 1;27(21):7406. doi: 10.3390/molecules27217406.
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 and . These intermediates were reduced to the corresponding 3,7-diazabicyclo[3.3.1]nonane targets. The oxime at C-9 was benzoylated to yield . 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-(1-imidazol-1-yl)propyl]-7-(3-methoxypropyl)-3,7-diazabicyclo[3.3.1]nonane () 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-(1-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane () increased both shoot and root length in only the Severyanka variety. The complex of 3-(3-butoxypropyl)-7-[3-(1-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane () 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.
我们报告了新型 3,7-双环[3.3.1]双哌啶的合成与表征，其分子中 N-3 位连接有一个咪唑丙基，N-7 位连接有 Boc 基团，C-9 位连接有苯甲酰氧基肟基团。这些化合物与β-环糊精[β-CD]络合，并作为所选小麦幼苗的种衣剂进行了评价。使用强酸，将 N-取代的哌啶酮与 N-3 和 N-7 位的合适咪唑丙基进行缩合，得到双哌啶酮和。这些中间体被还原为相应的 3,7-二氮杂双环[3.3.1]壬烷目标物。C-9 位的肟被苯甲酰化，得到。将这些 3,7-二氮杂双环[3.3.1]壬烷在乙醇中与β-CD 加热生成所需的配合物。我们研究了这些作为种衣剂的复合物保护和刺激三种小麦品种（哈萨克斯坦-10、塞瓦扬卡和米拉）生长的能力。3-[3-(1-咪唑-1-基)丙基]-7-(3-甲氧基丙基)-3,7-二氮杂双环[3.3.1]壬烷（）的复合物促进了哈萨克斯坦-10 中三种小麦品种根系生长超过 30%，塞瓦扬卡中 30%，米拉中 8.5%。3-Boc-7-[3-(1-咪唑-1-基)丙基]-3,7-二氮杂双环[3.3.1]壬烷（）的复合物仅增加了塞瓦扬卡品种的茎叶和根长。3-(3-正丁氧基丙基)-7-[3-(1-咪唑-1-基)丙基]-3,7-二氮杂双环[3.3.1]壬烷（）的复合物分别刺激了三种小麦品种的茎叶生长（0.8%、12.3%、13.5%）和根生长（12.3%、9.4%、21.7%）。双哌啶上取代基的性质影响其活性。作为粉末生成的固体配合物（1:1）在 240°C（分解）以上熔融，并通过元素分析确认为 1:1 配合物。
