121817-65-0Relevant articles and documents
Synthesis of zanthoxylamide protoalkaloids and their in silico ADME-Tox screening and in vivo toxicity assessment in zebrafish embryos
Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.
, p. 291 - 299 (2018/11/24)
Inspired by the simple and attractive structure of zanthoxylamide protoalkaloids: armatamide, rubecenamide, lemairamin, rubemamine and zanthosine; isolated from plants of the genus Zanthoxylum. We report the synthesis of a series of 29 substituted N-pheny
New Umami Amides: Structure-Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in Zanthoxylum piperitum
Frerot, Eric,Neirynck, Nathalie,Cayeux, Isabelle,Yuan, Yoyo Hui-Juan,Yuan, Yong-Ming
, p. 7161 - 7168 (2015/09/01)
A series of aromatic amides were synthesized from various acids and amines selected from naturally occurring structural frameworks. These synthetic amides were evaluated for umami taste in comparison with monosodium glutamate. The effect of the substituti
N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors
Michalet, Serge,Cartier, Gilbert,David, Bruno,Mariotte, Anne-Marie,Dijoux-franca, Marie-Genevieve,Kaatz, Glenn W.,Stavri, Michael,Gibbons, Simon
, p. 1755 - 1758 (2007/10/03)
As part of an ongoing project to identify plant natural products as efflux pump inhibitors (EPIs), bioassay-guided fractionation of the methanolic extract of Mirabilis jalapa Linn. (Nyctaginaceae) led to the isolation of an active polyphenolic amide: N-trans-feruloyl 4′-O-methyldopamine. This compound showed moderate activity as an EPI against multidrug-resistant (MDR) Staphylococcus aureus overexpressing the multidrug efflux transporter NorA, causing an 8-fold reduction of norfloxacin MIC at 292 μM (100 μg/mL). This prompted us to synthesize derivatives in order to provide structure-activity relationships and to access more potent inhibitors. Among the synthetic compounds, some were more active than the natural compound and N-trans-3,4-O-dimethylcaffeoyl tryptamine showed potentiation of norfloxacin in MDR S. aureus comparable to that of the standard reserpine.
AMIDES FROM ZANTHOXYLUM RUBESCENS
Adesina, Simeon K.,Reisch, Johannes
, p. 839 - 842 (2007/10/02)
The stem bark of Zanthoxylum rubescens has furnished two new amides identified as N-methyl,N-(3,4-dimethoxyphenylethyl)-3',4'-dimethoxycinnamamide (rubemamide) and N-(3,4-dimethoxyphenylethyl)-3,4'-dimethoxycinnamamide (rubemamin).Two other novel amides, N-methyl,N-(3,4-methylenedioxyphenylethyl)-3',4'-methylenedioxycinnamamide (dioxamide) and N-(3,4-methylenedioxyphenylethyl)-3',4'-methylene dioxycinnamamide (dioxamin) were isolated from the roots.The structural assignments of these amides were confirmed by synthesis.Both the root and stem barks furnished the known aromatic amide, N-methyl,N-(3,4-methylenedioxyphenylethyl)-cinnamamide (zanthomamide).In addition, lupeol and arnottianamide were isolated and characterized from the roots. - Key Word Index - Zanthoxylum rubescens; Rutaceae; stem bark; rubemamin; rubemamide; dioxamin; dioxamide; zanthomamide; arnottianamide; lupeol; unsaturated aromatic amides; pungent principles; synthesis.