Amino derivatives of glycyrrhetinic acid as potential inhibitors of cholinesterases

Schwarz, Štefan; Lucas, Susana D.; Sommerwerk, Sven; Csuk, René

doi:10.1016/j.bmc.2014.04.046

Cited by 52 publications

(34 citation statements)

References 39 publications

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“…Their absolute configuration at C-3 was deduced from their 1 H NMR spectra [coupling constant H-C (2)-H-C (3) and 2D-NOESY-NMR] as well as previous data reported in literature [26][27][28][29] . This reduction was not completely stereo-selective, but the epimers of opposite configuration at C-3 were only formed in minor amounts and could not be isolated [30][31][32][33][34] .…”

Section: Resultsmentioning

confidence: 91%

Synthesis and cytotoxicity of 3-amino-glycyrrhetinic acid derivatives

Sahn¹,

Grupe²,

Heller³

et al. 2018

Mediterr.J.Chem.,

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The aim of this study was to prepare 3-hydroximino- and 3-amino derivatives of glycyrrhetinic acid and derivatives to evaluate their in vitro cytotoxicity for a panel of human tumor cell lines. Thus, commercially available glycyrrhetinic acid (1) was acetylated or oxidized at position C-3 and transformed into a variety of different esters and amides followed by their conversion to 3-oximes and amines. While the parent compound was not cytotoxic at all, the 3-amino esters are highly cytotoxic. Interestingly, 3-amino amides were significantly less cytotoxic than 3-amino esters. The (3b, 18b, 20b) Benzyl 3-amino-11-oxoolean-12-en-30-oate was the most cytotoxic compound of this series showing an EC50 = 1.3 mM for 518A2 melanoma cells.

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Section: Resultsmentioning

confidence: 91%

Synthesis and cytotoxicity of 3-amino-glycyrrhetinic acid derivatives

Sahn¹,

Grupe²,

Heller³

et al. 2018

Mediterr.J.Chem.,

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“…Note that there are some published precedents where DCC-catalyzed esterification or amidation reactions stopped at the stage of intermediate product formation [20,21].…”

Section: Methodsmentioning

confidence: 99%

Functionalization of the double bond in the glycoside of the Stevia rebaudiana plant steviolbioside, as a way to macrocyclic glycosides

et al. 2015

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The С 16 =С 17 bond in the glycoside steviolbioside from the plant Stevia rebaudiana was oxidized for the first time. Ketone, thiosemicarbazone, and oxime of steviolbioside with a heptaacetylated sophorosyl fragment, as well as binuclear and tetranuclear macrocyclic derivatives of this rebaudioside were synthesized.The 1 Н NMR spectra of glycosides I-VI show characteristic signals of the С 20 Н 3 (0.99-1.23 ppm) and С 18 Н 3 protons (1.24-1.34 ppm), as well as the С 14 Н α proton as doublet at 2.70 ppm in stevioside I and as doublet of doublets at 2.46-2.56 ppm in glicosides II, IV. The anomeric protons of the sophorosyl fragment

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“…Both enzymes are widely distributed throughout the body; however, AChE remains the major cholinesterase within the human brain. BChE does not possess the same affinity for ACh as AChE does [1,2].…”

Section: Introductionmentioning

confidence: 91%

“…During the progress of AD, BChE activity is increased. Drugs which have been introduced into the treatment of AD are nonselective (rivastigmine) or AChE-selective inhibitors (galantamine or donepezil) [1,5]. In addition to the increased level of ACh, recent findings indicate that cholinesterase inhibitors can attenuate neuronal damage and protect them from cellular death, and therefore might affect AD pathogenesis and delay the progression.…”

Section: Introductionmentioning

confidence: 99%