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Synthesis of New α-Aminophosphonates Based on Cyclohexylamine
(Pleiades Publishing, 2020-06-01)
Аndrey V. Smolobochkin
;
Almir Sabirovich Gazizov
;
K. A. Doszhanova
;
A. B. Kuandykova
;
Б. Ж. Джиембаев
Abstract A series of new α-aminophosphonates was synthesized based on the acid-catalyzed Kabachnik–Fields reaction involving diethyl phosphite, cyclohexylamine and substituted benzaldehyde. Structure of the reaction products was established by IR, NMR spectroscopy, and mass spectrometry methods.
Цитирования (OpenAlex) 4Цитирования (OpenCitations) 4
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СИНТЕЗ НОВЫХ α-АМИНОФОСФОНАТОВ НА ОСНОВЕ ЦИКЛОГЕКСИЛАМИНОВ В УСЛОВИЯХ РЕАКЦИИ КАБАЧНИКА-ФИЛДСА
(2021-04-17)
K. A. Doszhanova
;
A. B. Kuandykova
;
Б. Ж. Джиембаев
;
Alexander Romanovich Burilov
New α-aminophosphonates were synthesized and characterized by the interaction of cyclohexylamine and 1-ethynyl-1-amino-cyclohexane with various benzaldehydes and diethyl phosphite under the conditions of the Kabachnik-Filds reaction. The composition and structure of the synthesized compounds were confirmed by IR, NMR 1 H and 31P spectroscopy References [1] Cherkasov R.A., Galkin V.I. Reakcija Kabachnika-Fildsa: Sinteticheskij potencial i problem mehanizma // Usp. himii. 1998. Vol. 67, vyp. 10. P. 940-968. [2] Kosyhova L.A., Pikshilingajte Ju.-V.K., Zaks A.S., Rabotnikov Ju.M. Sintezi protivo vospalitel'naja aktivnost' diamidofosforil'nyh proizvodnyh aminociklogeksana // Him-farm. zh. 1996. No. 5. P. 45-46. [3] Dzhiembaev B.Zh. α-оksi- α-aminofosfonatyshestichlennyh (N, O, S, Se) geterociklov. Almaty: Kompleks, 2003. 234 p. [4] Cherkasov R.A., Galkin V.I, Galkina I.V., Garifzjanov A.R., Sobanov A.A. Aminofosfo-naty: mehanizmy obrazovanija, reakcionnaja sposobnost' i analiticheskie svojstva // Butlerovskie soobshhenija. 2005. Vol. 6. P. 30-36. [5] Glushkov V.A., P'yankova O.S., Anikina L.V., Vikharev Yu.B., Feshina Ye.V., Shklyayev Yu.V., Tolstikov A.G. Sintez i neyrotropnaya aktivnost' proizvodnykh tsiklogeksilamina // Khim.-farm. registr. 2006. Vol. 40, No. 6. P. 80-84. [6] Pawel Kafarski, Micha Gornyvel Gorniak and Iga Andrasiak Kabachnik-Fields Reaction Under Green Conditions – A Critical Overview // Current Green Chemistry. 2015. 2. P. 218-222. [7] Mucha A., Kafarski P., Berlicki Ł. Remarkable Potential of ther-Aminophosphona-te/Phosphinate Structural Motif in Medicinal Chemistry J. Med. Chem. 2011. 54. 5955. [8] Adam Tajti, Erika Balint, Gyorgy Keglevich Micro wave-assisted synthesis of α-amino-phosphonates and related derivatives by the Kabachnik-Fields reaction // Phosphorus, Sulfur, and Silicon and the Related Elements. 2019. 194:4-6. P. 379-381. [9] Romanowska J., Kolodziej K., Sobkowski M., Rachwalak M., Jakubowski T., Golebiewska J., Kraszewski A., Boryski J., Dabrowska A., Stawinski J. Aryl H-phosphonates. 19. New anti-HIV pronucleotidephosphoramidatediesters containing amino- and hydroxypyridineauxiliaries // Eur. J. Med. Chem. 2019. 164. 47. [10] Romero-Estudillo I., Viveros-Ceballos J.L., Cazares-Carreno O., Gonzalez-Morales A., de Jesus B.F., Lopez-Castillo M., Razo-Hernandez R.S., Castaneda-Corral G., Ordonez M. 000Synthesis of new α-aminophosphonates: Evaluation as antiinflammatory agents and QSAR studies Bioorg. Med. Chem. 2019. 27. 2376. [11] Smolobochkin A.V., Gazizov, A.S. Doszhanova K.A., Dzhiyembayev B.Zh., Kuandyko-va A.B., Burilov A.R., Pudovik M.A Sintez novykh a-aminofosfonatov na osnove tsiklogeksilamina // Zhurnal organicheskoy khimii. 2020. Vol. 90, No. 6. P. 980-984. [12] Kuandykova A.B., Doszhanova K.A., Myrzakhmetova N.O., Kishibayev K.O. Sintez novykh a-aminofosfonatov v usloviyakh reaktsii Pudovika // Khimicheskiy zhurnal Kazakhstana. 2020. No. 1(69). P. 198-204.
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Synthesis of Amidophosphates Based on 1-Ethynyl-1-Aminocyclohexane Upon Microwave Activation and their Biological Activity
(2023-03-20)
Б. Ж. Джиембаев
;
A. B. Kuandykova
;
Nurgali Akylbekov
;
Alexey B. Dobrynin
;
Alexander Romanovich Burilov
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.
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Synthesis of New Symmetrical Diamidophosphates Based on meta-Phenylenediamine under Microwave Irradiation
(Pleiades Publishing, 2023-06-01)
A. B. Kuandykova
;
Б. Ж. Джиембаев
;
Alexander Romanovich Burilov
;
Nurgali Akylbekov
;
Elena Chugunova
Abstract A new series of diphosphorylated amidophosphates was obtained as a result of the reaction of meta-phenylenediamine with dialkyl phosphites in the presence of CCl4 and triethylamine (Atherton–Todd reaction) under microwave irradiation. Structure of all the obtained amidophosphates was established on the basis of 31P, 1H, 13C NMR, IR spectroscopy and mass spectrometry methods, as well as single crystal X-ray diffraction and elemental analysis data.
Цитирования (OpenAlex) 5Цитирования (OpenCitations) 2
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Synthesis of new symmetrical diamidophosphates based on meta-phenylenediamine under microwave irradiation
(Pleiades Publishing, 2023-06-15)
A. B. Kuandykova
;
Б. Ж. Джиембаев
;
Alexander Romanovich Burilov
;
Nurgali Akylbekov
;
Elena Chugunova
A new series of diphosphorylated amidophosphates was obtained as a result of the reaction of meta -phenylenediamine with dialkylphosphites in the presence of CCl4 and triethylamine (Atherton-Todd reaction) under microwave irradiation. Structure of all the obtained amidophosphates was established on the basis of 31P, 1H, 13C NMR, IR spectroscopy and mass spectrometry methods, as well as single crystal X-ray diffraction and elemental analysis data.
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New Derivatives of Coumarin-3-carboxylic Acid Containing a Furopyridine Fragment: Synthesis and Some Properties
(Pleiades Publishing, 2025-08-01)
Alexey Vladimirovich Trifonov
;
Nurbol Orynbasaruly Appazov
;
R. Kh. Bagautdinova
;
Lyudmila K. Kibardina
;
Michail A. Pudovik
Abstract As a result of this study, the first representative of coumarin-3-carboxylic acid containing a furopyridine fragment was obtained. It was demonstrated that this coumarin-3-carboxylic acid readily forms salts with various organic amines, diamines, as well as with alkali metal cations (Na, K) and ammonia. Testing of all obtained compounds against tumor cell lines M-HeLa and HuTu 80 revealed that a number of salt structures (specifically those based on 2-aminopyridine, 2,6-diaminopyridine, or sodium) exhibit cytotoxicity comparable to the reference drug, 5-fluorouracil.
Цитирования (OpenAlex) 1Цитирования (OpenCitations) 1

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