1-(3-AMINOPOPOPYL)IMIDAZOL AS A PRECURSOR OF PLANT GROWTH STIMULATORS

Abstract

Novel imidazole derivatives had been synthesized. The possibility of using 1-(3aminopropyl)imidazole as a starting reagent is synthetically justified for the preparing of piperidone-4 with following conversion into a bicyclic ketone. The reduction of mono- and bicyclic ketones had been carried out under Kizner-Wolf reaction conditions to imidazole-containing piperidine and bispidine, whose β-cyclodextrin complexes stimulate the growth of agricultural plants. The composition and structure of the compounds are confirmed by elemental analysis, IR and 13C NMR spectra.

References

[1] Popov S.Ja. Dorozhkina L.A., Kalinin V.A. Osnovy himicheskoj zashhity rastenij / Pod red. professora S. Ja Popova. M.: Art-Lion, 2003. 208 P.
[2] Tjuterev S.L. Himicheskie protraviteli. Protravlivanie semjan zernovyh kolosovyh kul'tur // Zashhita i karantin rastenij. 2005. P. 106-109.
[3] Wahbi Y., Tournaire C., Caujolle R., Payard M., Linas M.D., Seguela J.P. Aliphatic ethers and esters of 1-(2,4-dichlorophenyl)-2-(IH-imidazolyl)ethanol: study of antifungal activity against yeasts and hydrophobic character // Eur. J. Med. Chem. 1994. 29. P. 701-706.
[4] De Vita D., Scipione L., Tortorella S., Mellini P., Di Rienzo B., a Simonetti G., D'Auria F.D., Panella S., Cirilli R., Di Santo R., Palamara A.T. Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives // Eur. J. Med. Chem. 2012. 49. P. 334-342
[5] EP1675833A1. 1H-imidazole derivatives as cannabinoid receptor modulators / Josephus H.M. Lange, Cornelis G. Kruse Stuivenberg Herman H. VanHiskias G. Keizer. 2011-01-26.
[6] WO 2005/095354 20051013. Proizvodnye imidazola, aktivnye v otnoshenii receptora SV1/ Cheng Lejfeng, Lindstedt-Al'stermark Jeva-Lotte, Boije Anna Marija Persdotter. 27.12.2009. [7] http://www.findpatent.ru/patent/235/2354650.html
[8] https://www.eurolab.ua/medicine/atc/list/555/
[9] Yu V., Praliyev K., Nagimova A., Zazybin A. A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids // Tetrahedron Letters. 2015. Vol. 56. P. 1631-1634. (Impact Factor: 2.39) (Scopus).
[10] Yu V.K., Kabdraissova A.Zh., Praliyev K.D., Shin S.N., Berlin K.D. Synthesis and properties of novel alkoxy- and phenoxyalkyl ethers of secondary and tertiary ethynyl-piperdin-4ols possessing unusual analgesic, anti-bacterial, and anti-spasmotic activity as well as low toxicity //Journal of Saudi Chemical Society. 2009. 13. P. 209-217.
[11] Pichkhadze G. M., Smagulova G.S., Kadyrova D.M., Praliev K.D., Yu V.K. Local Anesthetic Activity of a Promising Piperidine Derivative (LAS-54) in Combination with Epine-phrine // Pharmaceutical Chemistry Journal December 2016. Vol. 50, Issue 9. P. 600–602. DOI 10.1007/s11094-016-1498-7. IF 0,461.
[12] Berlin K.D., Iskakova T.K., Faskhutdinov M.F., Praliyev K.D., Ch. P. Lee, Ten A Yu., Malmakova A. Unusual Conformational Behavior of 3,7-Dihetera(N,N-;N,O-;N,S-)bicyclo[3.3.1]nonan-9-ols in CDCl3 Phosphorus, Sulfur, and Silicon and the Related Elements. 2014. Vol. 189, N 7-8. P. 864-872.
[13] Astahova A.V., Demina N.B. Sovremennye tehnologii lekarstvennyh form: poluchenie, issledovanie i primenenie kompleksov vkljuchenija lekarstvennyh veshhestv s ciklodekstrinami // Him.-farmac. zhurn. 2004. Vol. 38, N 2. P. 46-49.
[14] Sharipov R.A. , Sharapov K.S., Kemelbekov U.S. , Volynkin V.A., Yu V.K., Panyushkin. The structure and pharmacological properties of the 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine inclusion complex with β-cyclodextrin // Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2016. 20 December. P. 1-8. DOI 10.1007/s10847-016-0685-1.
[15] Tkachuk O.A., Pavlikova E.V., Orlov A.N. Jeffektivnost' primenenija reguljatorov rosta pri vozdelyvanii jarovoj pshenicy v uslovijah lesostepnoj zony Srednego Povolzh'ja // Molodoj uchenyj. 2013. N 4. P. 677-679.