Synthesis and biological activity of cyclohexylamine derivatives

Глушков, В. А.; P’yankova, O. S.; Аникина, Л. В.; Vikharev, Yu. B.; Фешина, Е. В.; Shklyaev, Yu. V.; Толстиков, А. Г.

doi:10.1007/s11094-006-0114-7

Cited by 6 publications

(9 citation statements)

References 11 publications

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“…Less stable and more reactive cation B (for carbinols 1c (R 1 = nBu) and 1 d (R 1 = CH 3 )) undergoes the Ritter reaction with nitriles 2a-n leading to C which then is followed by intramolecular electrophilic ipso-cyclization to give spiran intermediate ( � )S. Formation of ( � )S is diastereospecific, a single diastereomer having two new stereocenters in the cis-attachement of Cyring is observed. [39,40]…”

Section: Resultsmentioning

confidence: 99%

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Metal‐Free Rapid Diastereoselective Construction of Isocryptolepine Core via Elecrophilic Dearomatization ‐ Inramolecular Michael Addition Sequence

Morozov

Shklyaev

2022

ChemistrySelect

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A method for rapid construction of indolo [3,2-l]acridin-7-one systems bearing isocryptolepine scaffold is described. Metalfree condensation of (4-methoxyphenyl)cyclohexan carbinols with ortho-amino/hydroxybenzonitriles in concentrated sulfuric acid yields polyannulated compounds with four new stereo-genic centers in a highly diastereoselective manner. The reaction includes elecrophilic dearomatization of methoxyarene, formation of spirocyclic intermediate and intramolecular 1,4-nucleophilic addition sequence.

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Section: Resultsmentioning

confidence: 99%

“…Formation of ( ± ) S is diastereospecific, a single diastereomer having two new stereocenters in the cis ‐attachement of Cy‐ring is observed [39,40] . As a consequence, carbons C‐2 and C‐6 of cyclohexadienone ring become chemically distinct.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Rapid Diastereoselective Construction of Isocryptolepine Core via Elecrophilic Dearomatization ‐ Inramolecular Michael Addition Sequence

Morozov

Shklyaev

2022

ChemistrySelect

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“…The IR spectra were recorded on a Bruker Alfa spectrometer in the range of 400-3600 cm -1 . The 1 H, 13 C, and 31 P NMR spectra were recorded on a Bruker AVANCE II-400 spectrometer with an operating frequency of 400.13 MHz, relative to the residual proton signals from the deuterated solvent (CDCl 3 ). H 3 PO 4 , 85% was used as the external standard.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (400 MHz, Chloroform-d) δ 4.15-4.08 (m, 4H), 2.93 (d, J = 7.2 Hz, 1H), 2.40 (s, 1H), 2.02 (d, J = 5.9 Hz, 2H), 1.62 (dd, J = 20.8, 9.3 Hz, 7H), 1.34 (t, J = 7.1 Hz, 6H). 13…”

Section: Methodsmentioning

confidence: 99%

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

Dzhiembaev.

Kuandykova

Akylbekov

et al. 2023

Eurasian Chem.-Technol. J.

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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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“…In these works, two titanium catalysts were studied, tetrakis(dimethylamino)titanium [Ti(NMe 2 ) 4 ] and tetrabenzyltitanium [TiBn 4 ], and it was observed that a better stereoselectivity was achieved by using the first catalyst while a better yield was obtained when the second catalyst was applied (Scheme 8B). Although the authors did not explore any possible biological activity of the obtained products, some compounds bearing an N-substituted cyclohexylamine moiety are known to present antidepressant and analgesic activities (e.g., compounds 19, 20, and 21, Scheme 8A) [75]. Further studies could reveal other notable biological activities, thus justifying the need to develop new and accessible titanium catalysts.…”

Section: Titanium-catalyzed C-h Activationmentioning

confidence: 99%

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Carvalho¹,

Miranda²,

Nunes³

et al. 2021

Beilstein J. Org. Chem.

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Several valuable biologically active molecules can be obtained through C–H activation processes. However, the use of expensive and not readily accessible catalysts complicates the process of pharmacological application of these compounds. A plausible way to overcome this issue is developing and using cheaper, more accessible, and equally effective catalysts. First-row transition (3d) metals have shown to be important catalysts in this matter. This review summarizes the use of 3d metal catalysts in C–H activation processes to obtain potentially (or proved) biologically active compounds.

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Synthesis and biological activity of cyclohexylamine derivatives

Cited by 6 publications

References 11 publications

Metal‐Free Rapid Diastereoselective Construction of Isocryptolepine Core via Elecrophilic Dearomatization ‐ Inramolecular Michael Addition Sequence

Metal‐Free Rapid Diastereoselective Construction of Isocryptolepine Core via Elecrophilic Dearomatization ‐ Inramolecular Michael Addition Sequence

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

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

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