10403-73-3Relevant academic research and scientific papers
Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition
Wang, Hailei,Ma, Yuping,Tian, Heng,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
, p. 2669 - 2673 (2014/04/03)
Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.
PROCESS FOR PRODUCTION OF HYDROXYTYROSOL USING ORGANOMETALLIC COMPOUNDS
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Page/Page column 15, (2012/02/02)
Disclosed is a process for the production of a 4-(2-hydroxyalkyl)-1,2-benzenediol, comprising the steps of (a) providing protected 1,2-benzenediol having the 1,2-hydroxyl groups protected, (b) halogenating the protected 1,2-benzenediol to obtain a protected 4-halo-1,2-benzenediol having the 1,2-hydroxyl groups protected, (c) reacting, in the presence of a metal or organometallic compound, the protected 4-halo-1,2-benzenediol to protected 4-(2-hydroxyalkyl)-1,2-benzenediol having the 1,2-hydroxyl groups protected, and (d) deprotecting the protected 4-(2-hydroxyalkyl)-1,2-benzenediol to obtain the 4-(2-hydroxyalkyl)-1,2-benzenediol. Also disclosed is the use of 1,2-benzenediol for the production of hydroxytyrosol.
First total synthesis of salvianolic acid C, tournefolic acid A, and Tournefolal
Shen, Si-Da,Zhang, Gui-Ping,Lei, Min,Hu, Li-Hong
experimental part, p. 204 - 213 (2012/06/01)
First total synthesis of the natural product salvianolic acid C, tournefolal and tournefolic acid A has been described. The key benzofuran skeletons are prepared via selective iodination and Sonogashira reaction. ARKAT-USA, Inc.
Synthesis and structure-function analysis of Fe(II)-form-selective antibacterial inhibitors of Escherichia coli methionine aminopeptidase
Wang, Wen-Long,Chai, Sergio C.,Ye, Qi-Zhuang
scheme or table, p. 1080 - 1083 (2009/08/07)
Methionine aminopeptidase (MetAP) is a promising target for the development of novel antibacterial, antifungal and anticancer therapy. Based on our previous results, catechol derivatives coupled with a thiazole or thiophene moiety showed high potency and selectivity toward the Fe(II)-form of Escherichia coli MetAP, and some of them clearly showed antibacterial activity, indicating that Fe(II) is likely the physiologically relevant metal for MetAP in E. coli and other bacterial cells. To further understand the structure-function relationship of these Fe(II)-form selective MetAP inhibitors, a series of catechol derivatives was designed and synthesized by replacement of the thiazole or thiophene moiety with different five-membered and six-membered heterocycles. Inhibitory activities of these newly synthesized MetAP inhibitors indicate that many five- and six-membered rings can be accommodated by MetAP and potency on the Fe(II)-form can be improved by introducing substitutions on the heterocyles to explore additional interactions with the enzyme. The furan-containing catechols 11-13 showed the highest potency at 1 μM on the Fe(II)-form MetAP, and they were also among the best inhibitors for growth inhibition against E. coli AS19 strain. These findings provide useful information for the design and discovery of more effective MetAP inhibitors for therapeutic applications.
Total synthesis of 5,5′,6,6′-tetrahydroxy-3,3′-biindolyl, the proposed structure of a potent antioxidant found in beetroot (Beta vulgaris)
Mee, Simon P. H.,Lee, Victor,Baldwin, Jack E.,Cowley, Andrew
, p. 3695 - 3712 (2007/10/03)
5,5′,6,6′-Tetrahydroxy-3,3′-biindolyl, the proposed structure of a phenolic antioxidant isolated from the red beetroot (Beta vulgaris), has been synthesised. The spectroscopic data of the synthetic material is not consistent with that reported for the natural product.
Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy
Hu, Mougang,Brasseur, Nicole,Zeki Yildiz,Van Lier, Johan E.,Leznoff, Clifford C.
, p. 1789 - 1802 (2007/10/03)
A series of benzyl-substituted phthalonitriles, substituted at the 3-, 4-, and 4,5-positions, underwent varied condensations with phthalonitrile to give a series of protected (monohydroxy- and polyhydroxyphthalocyaninato)zinc(II) derivatives which were readily cleaved to give several hydroxyphthalocyanines (ZnPc) (phthalocyanine phenol analogues). Their efficacy as sensitizers for the photodynamic therapy (PDT) of cancer was evaluated on the EMT-6 mammary tumor cell line. In vitro, the 2-hydroxy ZnPc (32) was the most active, followed by the 2,3- and 2,9- dihydroxy ZnPc (39 and 45), with the 2,9,16-trihydroxy ZnPc (33) exhibiting the least activity. In vivo, the monohydroxy derivative 32 and the 2,3- dihydroxy derivative 39 were both efficient in inducing tumor necrosis at 1 μmol kg-1, but complete tumor regression was poor, even at 2 μmol/kg. In contrast, the 2,9-dihydroxy isomer 45, at 2 μmol kg-1, induced tumor necrosis in all animals treated, with 75% complete regression. These results underline the importance of the position of the substituents on the Pc macrocycle to optimize tumor response and confirm the PDT potential of the unsymmetrical Pcs bearing functional groups on adjacent benzene rings.
Highly Efficient and Convenient Methods for the Direct Conversion of Aryl Silyl Ethers and Aryl Acetates into Aryl Alkyl Ethers
Oriyama, Takeshi,Noda, Kojiro,Yatabe, Kaori
, p. 701 - 703 (2007/10/03)
Direct conversion of aryl trialkylsilyl ethers and aryl acetates into the corresponding alkyl-protected phenols such as benzyl and allyl ethers can be conveniently performed by the reaction with alkyl halide in the presence of cesium fluoride and sodium methoxide, respectively, in a one-pot procedure.
HETEROCYCLIC HYDRAZIDE DERIVATIVES OF MONOCYCLIC BETA-LACTAM ANTIBIOTICS
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, (2008/06/13)
Antibacterial activity has been found in compounds of the formula. Compounds having the formula and pharmaceutically acceptable salts thereof, wherein: A is a bond or alkylene; Q completes a 5- or 6-membered saturated or unsaturated(including aromatic) heterocyclic ring having one or two, hetero atoms in the ring selected from nitrogen sulfur or oxygen; X is attached to an available carbon atom in the heterocyclic ring and is hydrogen or oxo; Y is attached to an available carbon atom in the heterocyclic ring and is hydrogen, amino, hydroxyl, halogen, carboxamide, nitrile, or carboxyl, except that Y is not carboxyl when the bicyclic ring completed by Q is 2-quinolyl, 3-quinolyl, or quinoxalyl; and the remaining symbols are as defined in the specification
1,5-EPOXY-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINS AND USE IN TREATMENT OF ULCERS
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, (2008/06/13)
The synthesis of epoxybenzazepin compounds is described. The novel compounds have anti-ulcer activity.
