- Structure–activity relationships and docking studies of hydroxychavicol and its analogs as xanthine oxidase inhibitors
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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.
- Nishiwaki, Keiji,Ohigashi, Kanae,Deguchi, Takahiro,Murata, Kazuya,Nakamura, Shinya,Matsuda, Hideaki,Nakanishi, Isao
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p. 741 - 747
(2018/07/05)
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- Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation
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Hydroalkoxylation is a powerful and efficient method of forming C-O bonds and cyclic ethers in synthetic chemistry. In studying the biosynthesis of the fungal natural product herqueinone, we identified an enzyme that can perform an intramolecular enantios
- Gao, Shu-Shan,Garcia-Borràs, Marc,Barber, Joyann S.,Hai, Yang,Duan, Abing,Garg, Neil K.,Houk,Tang, Yi
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p. 3639 - 3642
(2017/03/20)
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- Stereoselective syntheses of the 2-isopropenyl-2,3-dihydrobenzofuran nucleus: Potential chiral building blocks for the syntheses of tremetone, hydroxytremetone, and rotenone
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(Chemical Equation Presented) The first enantioselective synthesis of the 2-isopropenyl-2,3-dihydrobenzofuran skeleton of tremetone and hydroxytremetone from (E)-4-(2-hydroxyphenyl)-2-methyl-2-butenyl methyl carbonate and (E)-4-(2,6-dihydroxyphenyl)-2-met
- Pelly, Stephen C.,Govender, Sameshnee,Fernandes, Manuel A.,Schmalz, Hans-Guenther,De Koning, Charles B.
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p. 2857 - 2864
(2008/02/01)
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- Palladium-catalyzed, triethylborane-promoted C-allylation of naphthols and benzene polyols by direct use of allyl alcohols
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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.
- Kimura, Masanari,Fukasaka, Miki,Tamaru, Yoshinao
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p. 3611 - 3616
(2008/03/13)
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- Regioselectivity in aromatic Claisen rearrangements
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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
- Gozzo, Fabio Cesar,Fernandes, Sergio Antonio,Rodrigues, Denise Cristina,Eberlin, Marcos Nogueira,Marsaioli, Anita Jocelyne
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p. 5493 - 5499
(2007/10/03)
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- Base Catalysed Aromatic claisen Rearrengement of 3-Hydroxyphenyl Allyl Ethers
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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.
- Harwood, Laurence M.,Oxford, Anona J.,Thomson, Colin
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p. 1615 - 1617
(2007/10/02)
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