Silyl modification of biologically active compounds. 11. Synthesis, physico‐chemical and biological evaluation of <i>N</i>‐(trialkoxysilylalkyl)tetrahydro(iso,silaiso) quinoline derivatives

Zablotskaya, Alla; Segal, Izolda; Belyakov, Sergey; Lukevics, É.

doi:10.1002/aoc.1014

Cited by 20 publications

(2 citation statements)

References 24 publications

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“…and exhibit interesting biochemical activities [3,14] . For example, 2‐methyl‐tetrahydroquinoline ( 2 , R=H, R 1 =CH 3 , Scheme 1) is naturally occurring in human brain, and its derivatives ( 2 , R=OH, R 1 =alkyl) have been discussed as affine ligands for CNS receptors [14] possessing sedative and antinociceptive activities [14c,d] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons

2022

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Novel 2‐perfluoroalkylmethyl,4‐arylamino substituted tetrahydroquinolines (THQ) were expeditiously synthesized from perfluoroalkyl iodides RF−I and monosubstituted anilines. First, radical bis‐addition of vinyl acetate on RF−I afforded gem‐iodoacetoxy derivatives (newly characterized by NMR and MS) being actually masked/activated aldol synthons. Their reaction in 1 : 4 ratio with arylamines afforded title THQ under mild conditions in good yields (60–95 %) and diastereoselectivities (65 : 35–95 : 5 cis/trans isomer ratio); m‐substituted anilines regiospecifically lead to 7‐substituted THQ. Mechanistic investigation suggested the THQ formation to proceed through Michael then imine addition of two aniline units on an RF‐substituted crotonaldehyde intermediate, then through the cyclization of the resulting bis(arylamino/imino) intermediate through electrophilic aromatic substitution. Various RF (C6, C2, C4) and arylamine substitutions (p‐,o‐,m‐ alkyl, alkoxyl, halogen…) were thus exemplified.

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Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons

2022

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“…To overcome the problem of colloid system stability the parent alkanolamine has been modified by introduction of organosilicon substituent and by preparing of salt of silyl modified substance. Introduction of organosilicon substituent into the molecule of alkanolamine is an attractive and original approach to the lipophilicity increase [12][13][14][15] interaction with lipophilic chains of the first coating. The transformation of the compounds into salts in many cases causes activity increase, but also changes (increases) the solubility of the compounds in water, that is very significant for preparing and stabilization of water bilayer colloid systems, used for biological purposes.…”

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confidence: 99%

Synthesis and characterization of nanoparticles with an iron oxide magnetic core and a biologically active trialkylsilylated aliphatic alkanolamine shell

Zablotskaya

Segal

Maiorov

et al. 2007

Journal of Magnetism and Magnetic Materials

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Silyl modification of biologically active compounds. 12. Silyl group as true incentive to antitumour and antibacterial action of choline and colamine analogues

Zablotskaya

Segal

Popelis

et al. 2006

Applied Organom Chemis

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A series of triorganylsilyl(β-dialkylaminoethoxy)silanes was prepared and characterized by elemental analysis, 1 H, 13 C, 29 Si NMR and mass spectroscopy. Comparative study of 29 Si resonance of newly synthesized compounds showed correlation between its value and substituent nature at the silicon atom, and is shifted upfield for β-triorganyl(N,N-dialkylaminoethoxy)silanes in comparison with corresponding methiodides, revealing weak N ... Si interaction for proper silanes. In vitro antitumour and antimicrobial properties were investigated. The biological activity data exhibited a marked enhancement of inhibitory activity on trialkylsilylation against tumour cell lines and all the test bacterial/fungal strains.

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Silyl modification of biologically active compounds. 11. Synthesis, physico‐chemical and biological evaluation of N‐(trialkoxysilylalkyl)tetrahydro(iso,silaiso) quinoline derivatives

Cited by 20 publications

References 24 publications

Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons

Diastereoselective Synthesis of Perfluoroalkylmethyl‐Substituted 1,2,3,4‐Tetrahydroquinolines Derivatives through 1‐Iodo‐1,3‐bis(acetoxy) Synthons

Synthesis and characterization of nanoparticles with an iron oxide magnetic core and a biologically active trialkylsilylated aliphatic alkanolamine shell

Silyl modification of biologically active compounds. 12. Silyl group as true incentive to antitumour and antibacterial action of choline and colamine analogues

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