259267-38-4Relevant academic research and scientific papers
Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts
Schmidt, Bernd,Wolf, Felix
, p. 4386 - 4395 (2017/04/28)
The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.
Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor
Gargaro, Marco,Epifano, Francesco,Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Pirro, Matteo,Turco, Antonella,Puccetti, Paolo,Schmidt-Weber, Carsten B.,Fallarino, Francesca
, p. 1939 - 1943 (2017/06/28)
The aryl hydrocarbon receptor (AhR) is a transcription factor activated by a vast array of natural and synthetic ligands. It plays a pivotal role in numerous physiological and pathological responses, such as cell proliferation and differentiation, induction of xenobiotic metabolizing enzymes, response to environmental toxins, and several others. In this study, we investigated the ability of some natural compounds (oxyprenylated ferulic acid and umbelliferone derivatives) and their semisynthetic analogues (e.g., differently substituted 7-Alkoxycoumarins) to activate AhR, using a reporter luciferase assay. Among them, we found that 7-isopentenyloxycoumarin was the best AhR activator. Boropinic acid, 7-but-2′-enyloxycoumarin, 7-(2′,2′-dimethyl-n-propyloxy)coumarin, 7-benzyloxycoumarin, and 7-(3′-hydroxymethyl-3′-methylallyloxy)coumarin were also active, although to a lesser extent. All the compounds were also analyzed for their ability to inhibit AhR activation, using a reference ligand, 6-formylindolo[3,2-b]carbazole. Data recorded in the present investigation pointed out the importance of a 3,3-dimethylallyloxy side chain attached to the coumarin ring core as a key moiety for AhR activation.
Convenient synthesis of (E)-methyl O-alkylferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza
Mahajan, Rajesh P.,Patil, Shamkant L.,Mali, Raghao S.
, p. 328 - 331 (2007/10/03)
A convenient two step stereoselective synthesis of (E)-methyl O-alkylferulate 5a-c is described from vanillin 1. Reaction of vanillin 1 with allyl-, prenyl- or geranyl- bromide 2a-c has afforded alkyl ethers 3a-c which on reaction with phosphorane 4, under microwave irradiation, gives (E)-methyl O-alkylferulates 5a-c in high yield. In an alternative approach vanillin 1 on reaction with phosphorane 4 provides (E)-methyl ferulate 6 which on reaction with the corresponding bromides 2a-c gives (E)-methyl O-alkylferulates 5a-c.
In vitro inhibitory activity of boropinic acid against Helicobacter pylori
Epifano, Francesco,Menghini, Luigi,Pagiotti, Rita,Angelini, Paola,Genovese, Salvatore,Curini, Massimo
, p. 5523 - 5525 (2007/10/03)
In this study, we assessed in vitro minimum inhibitory concentration (MIC) values of some natural geranyloxycoumarins, geranyloxy- and isopentenyloxy acids against growth of Helicobacter pylori. Boropinic acid, active principle isolated from Boronia pinnata (Fam. Rutaceae), was seen to be the most effective compound with a MIC value of 1.62 μg/mL.
