{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,13]],"date-time":"2026-07-13T19:40:14Z","timestamp":1783971614729,"version":"3.55.0"},"reference-count":27,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,11,1]],"date-time":"2022-11-01T00:00:00Z","timestamp":1667260800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan","award":["AP08856051"],"award-info":[{"award-number":["AP08856051"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 \u03b2-cyclodextrin [\u03b2-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 \u03b2-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 \u00b0C (dec) and were characterized via elemental analyses as 1:1 complexes.<\/jats:p>","DOI":"10.3390\/molecules27217406","type":"journal-article","created":{"date-parts":[[2022,11,1]],"date-time":"2022-11-01T06:01:28Z","timestamp":1667282488000},"page":"7406","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Novel Complexes of 3-[3-(1H-Imidazol-1-yl)propyl]-3,7-diaza-bispidines and \u03b2-Cyclodextrin as Coatings to Protect and Stimulate Sprouting Wheat Seeds"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2805-3633","authenticated-orcid":false,"given":"Altynay B.","family":"Kaldybayeva","sequence":"first","affiliation":[{"name":"Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"},{"name":"Department of Chemistry and Technology of Organic Substances, Natural Compounds and Polymers, Al Farabi Kazakh National University, 71 Al-Farabi Ave, Almaty 050040, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6508-707X","authenticated-orcid":false,"given":"Valentina K.","family":"Yu","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aigul E.","family":"Malmakova","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tamara","family":"Li","sequence":"additional","affiliation":[{"name":"Laboratory of Cell Engineering, Institute of Plant Biology and Biotechnology, 45, Timiryazev Str., Almaty 050040, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9607-050X","authenticated-orcid":false,"given":"Assel Yu.","family":"Ten","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0079-4755","authenticated-orcid":false,"given":"Tulegen M.","family":"Seilkhanov","sequence":"additional","affiliation":[{"name":"Laboratory of the Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau University, 76, Abay St., Kokshetau 020000, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kaldybay D.","family":"Praliyev","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry of Synthetic and Natural Medicinal Substances, A.B. Bekturov Institute of Chemical Sciences, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenneth D.","family":"Berlin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oklahoma State University, Stillwater, OK 74078, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"9","DOI":"10.47287\/cen-09926-scicon4","article-title":"Double coating nurtures seeds","volume":"99","author":"Harwitz","year":"2021","journal-title":"Chem. Eng. News"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1038\/s43016-021-00315-8","article-title":"Programmable design of seed coating function induces water-stress tolerance in semi-arid regions","volume":"2","author":"Zvinavashe","year":"2021","journal-title":"Nat. Food"},{"key":"ref_3","first-page":"572","article-title":"Improving squash plant growth and yielding ability under organic fertilization condition","volume":"6","author":"Ezzo","year":"2012","journal-title":"Aust. J. Basic Appl. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2","DOI":"10.3389\/fpls.2016.02049","article-title":"Biostimulants in Plant Science: A Global Perspective","volume":"7","author":"Yakhin","year":"2017","journal-title":"Front. Plant Sci."},{"key":"ref_5","first-page":"70","article-title":"Effect of foliar application of growth regulators (GA3 and Ethereal) on growth, sex expression and yield of summer squash plants (Cucurbita peop L.) under plastic house condition","volume":"9","author":"Shafeek","year":"2016","journal-title":"Int. J. ChemTech Res."},{"key":"ref_6","first-page":"428","article-title":"Newly-developed hybrid \u201cLadushka\u201d","volume":"4","author":"Donskaya","year":"2016","journal-title":"Veg. Crops Russia"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"119","DOI":"10.21608\/ejoh.2020.41337.1142","article-title":"Organic stimulant uses in natural plant production","volume":"47","author":"Yucel","year":"2020","journal-title":"Egypt. J. Horticult."},{"key":"ref_8","first-page":"48","article-title":"The role of gibberellins and brassinosteroids in the regulation of growth and development of Arabidopsis","volume":"6","author":"Golovatskaya","year":"2007","journal-title":"Bull. TSPU"},{"key":"ref_9","unstructured":"Tarakanov, G.I., and Mukhina, V.D. (2002). The role of physiologically active substances in the regulation of the growth and development of vegetable plants. Vegetable Growing, Kolos-Moscow. [2nd ed.]. (In Russian)."},{"key":"ref_10","first-page":"94","article-title":"Application of plant growth regulators on crops cucurbitaceae family","volume":"2","author":"Mamonov","year":"2012","journal-title":"Izv. TSHA"},{"key":"ref_11","first-page":"6","article-title":"Application of growth regulators in winter cultivation wheat in forest-steppe conditions of the middle Volga region","volume":"1","author":"Koshelyaev","year":"2017","journal-title":"Izv. Samara State Agric. Acad."},{"key":"ref_12","unstructured":"Muromtsev, G.S., Chkanikov, D.P., Kulaeva, O.P., and Gamburg, K.Z. (1987). Fundamentals of Chemical Regulation of Plant Growth and Productivity, Agropromizdat\u2013Moscow. (In Russian)."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"791033","DOI":"10.3389\/fpls.2021.791033","article-title":"Endophytic Fungi: Symbiosis Second. Metab. Commun. Or Vice Versa?","volume":"12","author":"Alam","year":"2021","journal-title":"Front. Plant Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"49","DOI":"10.18286\/1816-45-2017-4-49-54","article-title":"Efficiency of application of growth regulators and Humic of fertilizers for growth, development and yield of spring grain wheat","volume":"4","author":"Suldin","year":"2017","journal-title":"Vestn. Ulyanovsk State Agric. Acad."},{"key":"ref_15","first-page":"677","article-title":"The effectiveness of the use of growth regulators in the cultivation of spring wheat in the forest-steppe zone of the Middle Volga region","volume":"4","author":"Tkachuk","year":"2013","journal-title":"Young Sci."},{"key":"ref_16","first-page":"42","article-title":"1-(3-Aminopropyl)imidazol as a precursor of plant growth stimulators","volume":"4","author":"Malmakova","year":"2018","journal-title":"Chem. J. of Kazakhstan"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/j.jscs.2009.04.001","article-title":"Synthesis and properties of novel alkoxy- and phenoxyalkyl ethers of secondary and tertiary ethynyl-piperdin-4-ols possessing unusual analgesic, anti-bacterial, and anti-spasmotic activity as well as low toxicity","volume":"13","author":"Yu","year":"2009","journal-title":"J. Saudi Chem. Soc."},{"key":"ref_18","unstructured":"Praliev, K.D., Yu, V.K., Baymoldina, S.N., and Fomicheva, E.E. (1991). 1-(3-n-butoxypropyl)-4-oxopiperidine, as an Intermediate in the Synthesis of 1-(3-N- butoxypropyl)-4-phenyl-4-propionyloxypiperidine Hydrochloride, Possesses an Analgesic. (1833618 USSR.MKI5 C07D 211\/64, A61K 31\/445), Activity. Patent, (In Russian)."},{"key":"ref_19","first-page":"645","article-title":"Cyclodextrins as pharmacetical as solubilizers","volume":"59","author":"Brewster","year":"2007","journal-title":"Adv. Drug Discov. Solubilizers"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"100811","DOI":"10.1016\/j.cdc.2021.100811","article-title":"X-Ray and NMR study of cyclodextrin inclusion complexes with 1-methyl-4-ethynyl-4-hydroxypipidine","volume":"37","author":"Kemelbekov","year":"2021","journal-title":"Chem. Data Collect."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5704","DOI":"10.1021\/jo980506o","article-title":"A practical synthesis of bicyclo3.3.1nonan-9-one","volume":"63","author":"Taeschler","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1515\/znb-1987-0217","article-title":"Stereochemitry of Substituted isomeric 3-0xa-7-azabicyclo3.3.1nonan-9-ones","volume":"42b","author":"Kuppers","year":"1987","journal-title":"Naturforsch"},{"key":"ref_23","unstructured":"Silverstein, R.M., Bassler, G.C., and Morrill, T.C. (1991). Spectrometric Identification of Organic Compounds, John Wiley & Sons."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4199","DOI":"10.1021\/jo00334a019","article-title":"Chair-boat conformer in 2,4,6,8-tetraphenyl-3-aza-7-thiabicyclo3.3.1nonan-9-one. An X-ray diffractionanalysis of asingle crystal of thecompound","volume":"46","author":"Pantaleo","year":"1981","journal-title":"J. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Krut\u2019ko, D.P., Medved\u2019ko, A.V., Lyssenko, K.O., Churakov, A.V., Dalinger, A.I., Kalinin, M.A., Gudovannyy, A.O., Ponomarev, K.Y., Suslov, E.V., and Vatsadze, S.Z. (2022). Bispidine platform as a tool for studying amide configuration stability. Molecules, 27.","DOI":"10.3390\/molecules27020430"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Suslov, E.V., Ponomarov, K.Y., Patrusheva, O.S., Kuranov, S.O., Okhina, A.A., Rogachev, A.D., Munkuev, A.A., Ottenbacher, R.V., Dalinger, A.I., and Kalinin, M.A. (2021). Novel bispidine\u2014Monoterpene conjugates\u2014Synthesis and application as ligands for the catalytic ethylation of chalcones. Molecules, 26.","DOI":"10.3390\/molecules26247539"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"336","DOI":"10.15616\/BSL.2020.26.4.336","article-title":"Anticancer activity of bispidinone derivative by apoptosis","volume":"26","author":"Kwon","year":"2020","journal-title":"Biomed. Sci. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/21\/7406\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:07:09Z","timestamp":1760144829000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/21\/7406"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,1]]},"references-count":27,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2022,11]]}},"alternative-id":["molecules27217406"],"URL":"https:\/\/doi.org\/10.3390\/molecules27217406","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,1]]}}}