Synthesis of Amidophosphates Based on 1-Ethynyl-1-Aminocyclohexane Upon Microwave Activation and their Biological Activity

Authors

  • B.J. Dzhiembaev Kazakh National Women’s Teacher Training University, 99, Aiteke bi str., Almaty, Kazakhstan
  • A.B. Kuandykova Kazakh National Women’s Teacher Training University, 99, Aiteke bi str., Almaty, Kazakhstan
  • N.I. Akylbekov A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8, Akad. Arbuzov str., Kazan, Tatarstan Republic, Russian Federation; Korkyt Ata Kyzylorda University, 29A, Aiteke bi str., Kyzylorda, Kazakhstan
  • A. Dobrynin A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8, Akad. Arbuzov str., Kazan, Tatarstan Republic, Russian Federation
  • A.R. Burilov A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8, Akad. Arbuzov str., Kazan, Tatarstan Republic, Russian Federation

DOI:

https://doi.org/10.18321/ectj1495

Keywords:

Atherton-Todd reaction, 1-ethynyl-1-aminocyclohexane, Dialkyl phosphorous acids, Microwave irradiation

Abstract

The researches for developing the methods for synthesizing new functionally substituted derivatives of alicyclic dialkylamidophosphates, establishing their structure, and searching for promising biologically active compounds in their series, are modern and relevant. The given study aimed to develop the synthesis of amidophosphates based on the example of phosphorylation of 1-ethynyl-1-aminocyclohexane with dialkyl phosphites in the presence of triethylamine in carbon tetrachloride in the Atherton-Todd reaction conditions using microwave irradiation of the reaction mixture. The reaction of 1-ethynyl-1-aminocyclohexane with dialkyl phosphites was carried out in a CCl4 excess at an equimolar ratio of reagents, triethylamine was used as an HCl acceptor. The highest yields of dialkyl- N-(1-ethynylcyclohexan-1-yl)amidophosphates were achieved by adding equimolar amounts of dialkyl phosphites to the mixture of 1-ethynyl-1-aminocyclohexane, triethylamine, and CCl4 followed by the subsequent activation of the mixture in a microwave reactor (MAS-II Plus MW) (MW 102 W, 115 °C, microwave irradiation time was 3‒5 min). The composition and structure of the obtained compounds were proved by elemental analysis, IR, 1H, 13C, 31P NMR spectroscopy, and X-ray diffraction analysis (XRD). The biological tests carried out in laboratory and field conditions allowed identifying diethyl-N-(1-ethynylcyclohexan-1-yl) amidophosphate among the synthesized compounds, which produces a high growth-regulating effect on the growth, development, and yield of agricultural crops.

References

(1). B.Zh. Dzhiembaev, α-oxy- and α-aminophos-phonates hexagonal (Ν, O, S, Se) heterocycles, Almaty, Kompleks, 2003, 234 p. [in Russian].

(2). E.E. Nifant’ev, Soros Educational Journal 7 (1996) 39‒46 [in Russian]. URL

(3). J. Romanowska, K. Kolodziej, M. Sobkowski, M. Rachwalak, et a., Eur. J. Med. Chem. 164 (2019) 47‒58. Crossref

(4). R. Bahadi, M. Berredjem, R. Redjemia, S. Bouacida, et al., Phosphorus, Sulfur, Silicon Relat. Elem. 197 (2022) 1248‒1254. Crossref

(5). A.V. Smolobochkin, A.S. Gazizov, K.A. Doszhanova, A.B. Kuandykova, et al., Russ. J. Gen. Chem. 90 (2020) 1100–1103. Crossref

(6). I. Romero-Estudillo, J.L. Viveros-Ceballos, O. Cazares-Carreño, A. González-Morales, et al., Bioorg. Med. Chem. 27 (2019) 2376‒2386. Crossref

(7). Patent KZ 35444. Application of N-(1- ethylcyclohexyl)amide O,O-diethyl phosphoric acid as a growth stimulator of vegetable crops. B.Zh. Dzhiembaev, A.B. Kuandykova, K.A. Doszhanova, A.A. Tleubaeva et al. Bull. #52, 2021.

(8). I.H. Kim, Y.K. Park, H. Nishiwaki, B.D. Hammock, et al., Med. Chem. 23 (2015) 7199‒7210. Crossref

(9). F.M. Harassova, D.Sh. Safina, N-Amine Phosphorylation by Todd-Atterton. Review (N-Fosforilirovanie aminov po Toddu- Attertonu. Obzor. F.M. Harrasova, D.Sh. Safina, Dep. rukopisi. No 250. – HP 92 ot 5.08.92. RZhHim. 1993. 8 Zh 357 Dep.) [in Russian].

(10). R. Bahadi, R. Boughoula, M. Berredjem, K. Bachari, et al., Phosphorus, Sulfur, Silicon Relat. Elem. 197 (2022) 1150‒1156. Crossref

(11). R. Aissa, S. Guezane-Lakoud, L. Gali, M. Toffano, et al., J. Mol. Struct. 1247 (2022) 131336. Crossref

(12). L.A. Kosykhova, Yu.V.K. Pikshilingaite, A.S. Zaks, Yu.M. Rabotnikov, Pharm. Chem. J. 30 (1996) 330‒331. Crossref

(13). V.A. Glushkov, O.S. P’yankova, L.V. Anikina, Yu.B. Vikharev, et al., Pharm. Chem. J. 40 (2006) 298‒302. Crossref

(14). H.R. Hudson, Á.. Tajti, E. Bálint, M. Czugler, et al., Synth. Commun. 50 (2020) 1446‒1455. Crossref

(15). S. Poola, S. Nagaripati, S. Tellamekala, V. Chintha, et al., Synth. Commun 50 (2020) 2655‒2672. Crossref

(16). S.K. Tukanova, B.Zh. Dzhiembaev, B.M. Butin, Fosforilirovanie 1-jetinil-1-aminociklogeksana dialkilfosforistymi kislotami, Zh. obshh. himii. 59 (1989) 2633–2634 (in Russian).

(17). Patent KZ 35532. Application of 0,0-dieth-yl-1-(3,4-dimethoxyphenyl)-(1-ethynylcyclo-hexylaminomethyl) phosphonate as a growth stimulator of vegetable crops. B.Zh. Dzhiembaev, A.B. Kuandykova, K.A. Doszhanova, A.A. Tleubaeva et al. Bull. #8, 2022.

(18). A.B. Kuandykova, B.Zh. Dzhiembaev, K.A. Doszhanova, Bulletin of the National Engineering Academy of the Republic of Kazakhstan 4 (2019) 66‒72 [in Russian].

(19). L.I. Minaeva, L.S. Patrikeeva, M.M. Kabachnik, I.P. Beletskaya, Russ. J. Org. Chem. 46 (2010) 1579–1580. Crossref

(20). V.I. Krutikov, A.V. Erkin, V.V. Krutikova, Russ. J. Gen. Chem. 82 (2012) 822–826. Crossref

(21). Z. Rádai, N.Z. Kiss, Z. Mucsi, G. Keglevich, Phosphorus, Sulfur, Silicon Relat. Elem. 191 (2016) 1564‒1565. Crossref

(22). A. Adhikari, S. Bhakta, T. Ghosh, Tetrahedron 126 (2022) 133085. Crossref

(23). G.M. Sheldrick, T.R. Schneider, Methods Enzymol. 277 (1997) 319–343. PMID: 18488315

(24). A. Altomare, G. Cascarano, C. Giacovazzo, D. Viterbo, Acta Cryst. 47 (1991) 744‒748. Crossref

(25). G.M. Sheldrick, (1997) SHELXS97 and SHELXL97. Program for Crystal Structure Solution and Refinement. University of Göttingen, Göttingen. URL

(26). L.J. Farrugia J. Appl. Crystallogr. 32 (1999) 837‒838. Crossref

(27). APEX2 (Version 2.1) (2006). SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS Inc., Madison. Wisconsin. USA URL

(28). A.L. Spek, Acta Cryst. 65 (2009) 148‒155. Crossref

Downloads

Published

2023-03-20

How to Cite

Dzhiembaev, B., Kuandykova, A., Akylbekov, N., Dobrynin, A., & Burilov, A. (2023). Synthesis of Amidophosphates Based on 1-Ethynyl-1-Aminocyclohexane Upon Microwave Activation and their Biological Activity. Eurasian Chemico-Technological Journal, 25(1), 57–64. https://doi.org/10.18321/ectj1495

Issue

Section

Articles