Design, Synthesis and Evaluation of Genistein-polyamine Conjugates as Multi-functional Anti-Alzheimer Agents

Luo, Wen

doi:10.4172/2161-0444.1000203

Cited by 6 publications

(10 citation statements)

References 17 publications

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“…The use of unconventional MW-US factors supporting the chemical reaction has been successful in achieving the planned compound in a direct way. The only derivative obtained was 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yloxy) acetic acid ( 31 ), similarly to in other literature reports [ 34 ]. Nipagins, i.e., the esters of p-hydroxybenzoic acid ( 5 and 6 ) are monophenols, which in the reaction with chloroacetic acid give their ether derivatives 20 and 21 .…”

Section: Resultssupporting

confidence: 86%

“…The identity of the compounds obtained was confirmed by physicochemical method and by MS spectrometry. The physicochemical and spectral data of all compounds obtained ( 17 – 20 , 23 – 27 , 29 – 31 ) have been confirmed by literature data [ 34 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. The identities of compounds 17 , 21 – 23 and 28 were confirmed by additional spectral analysis.…”

Section: Methodssupporting

confidence: 82%

“…Despite the presence of more than one phenolic group in their molecules, monoether derivatives were only obtained by the reaction with chloroacetic acid under the conditions used. This is partly known from references [ 32 , 33 , 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…As a result of the reaction with chloroacetic acid 16 , only the monosubstituted ether derivative 31 is formed. However, under standard conditions, genistein is easily reacted with halogenoacetic acid ethyl ester in acetone and a catalytic amount of iodine or potassium iodide, leading to the corresponding monosubstituted ether derivative with an ester group [ 34 ]. Under the above classical conditions, the product of direct reaction of genistein 15 and free halogenoacetic acid was not obtained.…”

Section: Resultsmentioning

confidence: 99%

“…2-[5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yloxy)] acetic acid ( 31 ) [ 34 ]: in the reaction of 15 and 16 the product 31 , after column chromatography, was obtained as a light-brown fine crystals (41%); m.p. 257–259 °C; R f sub = 0.45; R f prod = 0 (CHCl 3 : MeOH 9:1); MS m / z (%): 328.0 (100.0) [M + ], 283.0 (21.1), 269.0 (63.4), 241.0 (21.1), 148.9 (12.1), 123.9 (10.4), 88.8 (2.3).…”

Section: Methodsmentioning

confidence: 99%

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Microwave (MW), Ultrasound (US) and Combined Synergic MW-US Strategies for Rapid Functionalization of Pharmaceutical Use Phenols

et al. 2018

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Increasingly stringent regulations aimed at protection of the natural environment have stimulated the search for new synthetic methodologies in organic and medicinal chemistry having no or minimum harmful effect. An interesting approach is the use of alternative activation factors, microwaves (MW) or ultrasounds (US) and also their cross-combination, which has been tested in the fast and efficient creation of new structures. At present, an easy and green hybrid strategy (“Lego” chemistry) is generally recommended for the design of new substances from different chemistry building blocks. Often, selected biologically active components with specific chemical reactivities are integrated by a suitably designed homo- or heterodifunctional linker that modifies the functionality of the starting structure, allowing easy covalent linkage to another molecule. In this study, a fast introduction of heterodifunctional halogenoacidic linker to selected mono-, di- and triphenolic active substances, allowing their functionalization, was investigated. Nucleophilic substitution reaction was chosen to produce final ethers with the reactive carboxylic group from phenols. The functionalization was performed using various green factors initiating and supporting the chemical reactions (MW, US, MW-US). The benefits of the three green supporting methods and different conditions of reactions were analyzed and compared with the results of the reaction performed by conventional methods.

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Section: Resultssupporting

confidence: 86%