1616-52-0Relevant academic research and scientific papers
The first diastereoselective synthesis of cinerins A-C, PAF-antagonistic macrophyllin-type bicyclo[3.2.1]octane neolignans, using a novel Pd-catalysed oxyarylation
Coy B., Ericsson D.,Cuca S., Luis E.,Sefkow, Michael
, p. 2003 - 2005 (2010)
The first diastereoselective synthesis of PAF-antagonistic cinerins A-C, macrophyllin-type bicyclo[3.2.1]octane neolignans from Pleurothyrium cinereum, has been accomplished using a novel Pd-catalysed oxyarylation to afford a 2,3-dihydrobenzofuran as the key intermediate.
Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle
Horii, Toshihiro,Itagaki, Sawako,Kawano, Tomikazu,Miyoshi, Akihito,Murakami, Nobutoshi,Tamura, Satoru
, p. 784 - 790 (2020/09/18)
Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection “hot-spots,” medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure–activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.
Structure–activity relationships and docking studies of hydroxychavicol and its analogs as xanthine oxidase inhibitors
Nishiwaki, Keiji,Ohigashi, Kanae,Deguchi, Takahiro,Murata, Kazuya,Nakamura, Shinya,Matsuda, Hideaki,Nakanishi, Isao
, p. 741 - 747 (2018/07/05)
Hydroxychavicol (HC), which is obtained from the leaves of Piper betle LINN. (Piperaceae), inhibits xanthine oxidase (XO) with an IC50 value of 16.7μM, making it more potent than the clinically used allopurinol (IC50=30.7μM). Herein, a structure–activity relationship analysis of the polar part analogs of HC was conducted and an inhibitor was discovered with a potency 13 times that of HC. Kinetic studies have revealed that HC and its active analog inhibit XO in an uncompetitive manner. The binding structure prediction of these inhibitor molecules to the XO complex with xanthine suggested that both compounds (HC and its analog) could simultaneously form hydrogen bonds with xanthine and XO.
Palladium-catalyzed, triethylborane-promoted C-allylation of naphthols and benzene polyols by direct use of allyl alcohols
Kimura, Masanari,Fukasaka, Miki,Tamaru, Yoshinao
, p. 3611 - 3616 (2008/03/13)
The combination of a catalytic amount of Pd(0) species and triethylborane promotes the C-allylation of benzene polyols and naphthols at room temperature to 50 °C by the direct use of a variety of allylic alcohols; Exhaustive allylation of 1,3-benzenediol and 1,3,5-benzenetriol provides penta-allylation and hexa-allylation products, respectively, in good yields. Georg Thieme Verlag Stuttgart.
Regioselectivity in aromatic Claisen rearrangements
Gozzo, Fabio Cesar,Fernandes, Sergio Antonio,Rodrigues, Denise Cristina,Eberlin, Marcos Nogueira,Marsaioli, Anita Jocelyne
, p. 5493 - 5499 (2007/10/03)
Theoretical calculations and the isomeric product composition for a series of eight meta-substituted allyl aryl ethers confirm the reliability of a new 1H NMR methodology used to predict aromatic Claisen regioselectivity from ground-state confo
Base Catalysed Aromatic claisen Rearrengement of 3-Hydroxyphenyl Allyl Ethers
Harwood, Laurence M.,Oxford, Anona J.,Thomson, Colin
, p. 1615 - 1617 (2007/10/02)
The 3-hydroxyphenyl allyl ethers (1a-d) have been shown to undergo rearrangement in refluxing aqueous methanolic potassium hydroxide in the presence of oxygen, whereas no reaction occurs in the absence of base and oxygen, and the products formed are the result of accelerated sigmatropic processes in which moderate regioselection is operating; evidence is presented for the process being radical rather than anion mediated.
