- The influence of the p-alkyl substituent on the isomerization of o- quinones to p-quinone methides: Potential bioactivation mechanism for catechols
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Previously, we have shown that an additional bioactivation pathway for the hepatocarcinogen safrole (1-allyl-3,4-(methylenedioxy)benzene) exists which may contribute to its toxic effects: initial O-dealkylation of the methylenedioxy ring, forming the catechol, hydroxychavicol (HC, 1-allyl-3,4- dihydroxybenzene), 2-electron oxidation to the o-quinone (4-allyl-3,5- cyclohexadien-1,2-dione), and isomerization, forming the more electrophilic p-quinone methide (2-hydroxy-4-allylidene-2,5-cyclohexadien-1-one) [Bolton, J. L., Acay, N. M., and Vukomanovic, V. (1994) Chem. Res. Toxicol. 7, 443- 450]. In the present investigation, we explored the effects of changing π- conjugation at the 4-position on both the rate of isomerization of the initially formed o-quinones to the QMs and the reactivity of the quinoids formed from 4-propylcatechol (1), 2,3-dihydroxy-5,6,7,8-tetrahydronaphthalene (2), and 4-cinnamylcatechol (3). We selectively oxidized the catechols to the corresponding o-quinones or p-quinone methides and trapped these reactive electrophiles with glutathione (GSH). The GSH adducts were fully characterized by UV, NMR, and mass spectrometry. Microsomal incubations with the parent catechols in the presence of glutathione produced only o-quinone glutathione conjugates. However, if the trapping agent (GSH) was added after an initial incubation time, both o-quinone and p-quinone methide GSH conjugates were observed. The results indicate that extended π-conjugation at the para position enhances the rate of isomerization of the o-quinone to the quinone methide. Thus the half-life of the o-quinones decreased in the following order: the o-quinone of 1 > 2 > HC > 3. In support of this, AM1 semiempirical calculations also showed the same trend: an increase in stability of the quinone methide relative to the o-quinone with extending π- conjugation at the 4-position. Finally, kinetic studies showed that the reactivity of the quinone methides with water increases with decreasing π- conjugation. These data provide further evidence that formation of these electrophilic quinone methides from o-quinones may be a general bioactivation pathway for synthetic and naturally occurring 4-alkylcatechols.
- Iverson,Li Qing Hu,Vukomanovic,Bolton
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Read Online
- Renewable Thermoplastics Based on Lignin-Derived Polyphenols
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A series of renewable triphenylmethane-type polyphenols (TPs) were synthesized from lignin-derived guaiacols (methylguaiacol and propylguaiacol) and aldehydes (4-hydroxybenzaldehyde, vanillin, and syringaldehyde). By converting guaiacols to catechols through ortho-demethylation, the newly formed phenolic para site remarkably improved the reactivity as reflected by conversion of TPs. Optimized reagent molar ratios were aldehyde/catechol (1:4) and aldehyde/H2SO4 (1:3). A typical TP (VAN-M-CAT) was converted to glycidyl ether (GE-VAN-M-CAT) to examine its feasibility as precursor to epoxy thermosets. The resulting network exhibited excellent glassy modulus (12.3 GPa), glass transition temperature (167 °C), and thermal stability, which were attributed to the rigid triphenylmethane framework, high functionality (n = 5), and high cross-link density. A fully biobased epoxy comonomer (VAN-LIN-EPO), which was prepared by esterification of VAN-M-CAT with linoleic acid followed by epoxidation, could tune the material properties. This study widens the synthesis route of fully biobased polyphenols, which can yield polymers with excellent properties.
- Zhao, Shou,Abu-Omar, Mahdi M.
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Read Online
- Efficient demethylation of aromatic methyl ethers with HCl in water
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A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.
- Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
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supporting information
p. 1995 - 2009
(2021/03/26)
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- Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
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An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
- Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
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supporting information
p. 3063 - 3068
(2020/02/05)
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- Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal
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Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.
- Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan
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p. 6429 - 6440
(2020/07/14)
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- Selective ether bond breaking method of aryl alkyl ether
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The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.
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Paragraph 0119-0123
(2020/09/16)
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- One-pot hydrodeoxygenation (HDO) of lignin monomers to C9 hydrocarbons co-catalysed by Ru/C and Nb2O5
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A physical mixture of Ru/C and Nb2O5 is an effective catalyst for upgrading lignin monomers under low H2 pressure at 250 °C to a clean cut of hydrocarbon liquid fuels. The reaction solvent is water with a small amount of methanol additive. Hydrodeoxygenation (HDO) was evaluated using dihydroeugenol (DHE) as an exemplary lignin monomer model. Under optimized conditions, 100% conversion of DHE and very high selectivity to propyl cyclohexane (C9 hydrocarbon) was achieved. Nb2O5 was prepared at a low temperature (450 °C) and was shown to contain acid sites that enhance the production of fully deoxygenated products. The methanol additive serves as a hydrogen source for the Ru/C catalysed reduction of the aromatic ring. In addition, when a substrate mixture of DHE, isoeugenol and 4-allylsyringol simulating lignin products was employed, 100% conversion to propyl cyclohexane (76%) and propyl benzene (24%) was observed, thereby suggesting the general applicability of this catalyst system for funneling lignin monomers into a clean cut of hydrocarbon liquid fuels. This study sheds light on the function of each catalyst component and provides a simple and green utilization of biomass monomers as a feedstock for renewable hydrocarbon fuels. This journal is
- Abu-Omar, Mahdi M.,Ford, Peter C.,Li, Simin,Liu, Baoyuan,Luo, Zhongyang,Truong, Julianne
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supporting information
p. 7406 - 7416
(2020/11/25)
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- Low-Temperature Catalytic Hydrogenolysis of Guaiacol to Phenol over Al-Doped SBA-15 Supported Ni Catalysts
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Selective hydrogenolysis of aromatic carbon-oxygen (Caryl?O) bonds is a key strategy for the generation of aromatic chemicals from lignin. However, this process is usually operated at high temperatures and pressures over hydrogenation catalysts, resulting in a low selectivity for aromatics and an extra consumption of hydrogen. Here, a series of Al-doped SBA-15 mesoporous materials with different Si/Al molar ratios (Al-SBA-15) were prepared via a post-synthesis method using NaAlO2 as the Al source, and then Al-SBA-15 supported Ni catalysts (Ni/Al-SBA-15) were prepared by a deposition-precipitation method using urea as the hydrolysis reagent. The prepared supports and catalysts were extensively characterized using various techniques such as XRD, N2 adsorption/desorption, TEM, 27Al NMR, NH3-TPD, XPS, H2-TPR, and pyridine-FT-IR, and the catalysts were evaluated in the hydrogenolysis of the Caryl?O bond in guaiacol and lignin derived compounds under mild conditions. The effects of the Si/Al ratio in catalyst and reaction parameters on guaiacol conversion and product distribution were investigated in detail, associated with solvent effect. The incorporation of Al into the framework of SBA-15 can improve the Lewis acidity and the dispersion of the supported Ni particles and yet modulate the metal-support interactions, which are propitious to the hydrogenolysis of the Caryl?O bond in guaiacol. The catalyst Ni/Al-SBA-15 with a Si/Al molar ratio of 10 shows the best performance with a guaiacol conversion of 87.4 % and a phenol selectivity of 76.9 % under the mild conditions conducted, because of its proper acidity, suitable metal-support interactions, and high dispersion of the active species. The present study would stimulate research and development in multi-functional catalysts for the generation of valuable chemicals from biomass.
- Wang, Qiuyue,Chen, Yufang,Yang, Guanheng,Deng, Ping,Lu, Xinqing,Ma, Rui,Fu, Yanghe,Zhu, Weidong
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p. 4930 - 4938
(2020/08/26)
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- Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle
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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.
- Horii, Toshihiro,Itagaki, Sawako,Kawano, Tomikazu,Miyoshi, Akihito,Murakami, Nobutoshi,Tamura, Satoru
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p. 784 - 790
(2020/09/18)
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- METHOD FOR THE DEACYLATION AND/OR DEALKYLATION OF COMPOUNDS
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The present invention in general relates to a method for the deacylation and/or dealkylation (both O-dealkylation as well as C-dealkylation) of compounds, more specifically of aromatic compounds. The method is characterized by contacting the compound with an acid-containing aqueous reaction mixture using high temperature and high pressure conditions. The invention also provides a method for preparing a compound suitable for further deacylation using the method of the invention.
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Page/Page column 23; 37
(2019/02/15)
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- Carbamate Synthesis Using a Shelf-Stable and Renewable C1 Reactant
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4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50–80 °C in the presence of a Lewis acid catalyst, such as Zn(OAc)2?2 H2O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.
- Dobi, Zoltán,Reddy, B. Narendraprasad,Renders, Evelien,Van Raemdonck, Laurent,Mensch, Carl,De Smet, Gilles,Chen, Chen,Bheeter, Charles,Sergeyev, Sergey,Herrebout, Wouter A.,Maes, Bert U. W.
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p. 3103 - 3114
(2019/06/24)
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- Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide
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Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
- Sang, Dayong,Tian, Juan,Tu, Xiaodong,He, Zhoujun,Yao, Ming
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p. 704 - 712
(2019/01/23)
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- Ether bond cracking method of phenylalkyl ether
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The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.
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Paragraph 0084-0089
(2018/11/26)
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- METHOD OF PREPARING AROMATIC COMPOUNDS FROM LIGNIN
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The invention relates to a method of preparing monocyclic aromatic compounds from lignin and to the use of the method and/or the aromatic compounds obtained by the method according to the invention in the production of fuels, electronic components, plastic polymers, rubber, medicines, vitamins, cosmetic products, perfumes, foodstuffs, synthetic threads and fibres, synthetic leathers, adhesives, pesticides and fertilizers. The invention also relates to a method of producing fuels, electronic components, plastic polymers, rubber, medicines, vitamins, cosmetic products, perfumes, foodstuffs, synthetic threads and fibres, synthetic leathers, adhesives, pesticides and fertilizers, including a step of preparing aromatic compounds from lignin using the method according to the invention.
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Paragraph 0267
(2017/06/12)
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- Pyridine Improves Aluminum Triiodide Induced Selective Cleavage of Alkyl o -Hydroxyphenyl Ethers: A Practical and Efficient Procedure for the Preparation of Hydroxychavicol by Demethylation of Eugenol
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Demethylation of eugenol with aluminum triiodide is complicated by an unexpected hydrogenation side reaction. The hydrogenation proceeds through a cascade deprotonation, hydroiodination, and hydrogen-halogen exchange process, and can be prevented by suppressing the hydroiodination in advance. A practical demethylation procedure is thus developed that delivers hydryoxychavicol in essentially quantitative yield by using pyridine as an additive. The method is selective towards cleaving alkyl o-hydroxyphenyl ethers and is compatible with a variety of functional groups.
- Sang, Dayong,Yao, Ming,Tian, Juan,Chen, Xiaoman,Li, Li,Zhan, Hongju,You, Linhong
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p. 138 - 142
(2016/12/26)
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- Conversion of Simple Cyclohexanones into Catechols
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A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.
- Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Zou, Miancheng,Tang, Conghui,Liang, Yujie,Song, Song,Jiao, Ning
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supporting information
p. 12271 - 12277
(2016/09/28)
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- Chemo- and Regioselective Hydrogenolysis of Diaryl Ether C-O Bonds by a Robust Heterogeneous Ni/C Catalyst: Applications to the Cleavage of Complex Lignin-Related Fragments
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We report the chemo- and regioselective hydrogenolysis of the C-O bonds in di-ortho-substituted diaryl ethers under the catalysis of a supported nickel catalyst. The catalyst comprises heterogeneous nickel particles supported on activated carbon and furnishes arenes and phenols in high yields without hydrogenation. The high thermal stability of the embedded metal particles allows C-O bond cleavage to occur in highly substituted diaryl ether units akin to those in lignin. Preliminary mechanistic experiments show that this catalyst undergoes sintering less readily than previously reported catalyst particles that form from a solution of [Ni(cod)2].
- Gao, Fang,Webb, Jonathan D.,Hartwig, John F.
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supporting information
p. 1474 - 1478
(2016/02/12)
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- SUBSTITUTED CATHECHOLS AS INHIBITORS OF IL-4 AND IL-5 FOR THE TREATMENT BRONCHIAL ASTHMA
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The present invention relates to compounds of general formula 1 for the treatment of bronchial asthma by inhibition of IL-4 or IL-5 pathway inhibition. The present invention also relates to the use of compound of general formula 1 for the treatment of bronchial by inhibition of IL-4 or IL-5 pathway. The present invention also relates to the method of treating asthma by inhibition of IL-4 or IL-5 pathway by administration of compound or said composition through oral, intranasal, route or by inhalation to a mammal in need thereof. Compound of general formula 1 may be used for reducing perivascular and peribronchial inflammation.
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- PROCESS FOR THE CONVERSION OF LIGNIN TO LIQUID HYDROCARBONS
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Process for the conversion of lignin to liquid hydro-carbons comprising: subjecting the lignin to hydrogenolysis in the presence of at least one hydrogenolysis catalyst, at a temperature ranging from 250° C. to 350° C., preferably ranging from 290° C. to 320 ° C., so as to obtain depolymerized lignin; subjecting said depolymerized lignin to hydrotreating so as to obtain a mixture of liquid hydrocarbons. Said liquid hydrocarbons can be used as such (biofuels) for the production of reformulated gasolines, or they can be used for the production of gasolines or of gas oils through conventional refining processes.
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Paragraph 0153-0168
(2013/03/26)
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- INHIBITORS OF PHOSPHATIDYLINOSITOL-3-KINASE (PI3) AND INDUCERS OF NITRIC OXIDE (NO)
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The present invention relates to compounds of general formula 1 for the treatment of malignancy by inhibition of PI3-Akt pathway and or induction of NO. The present invention also relates to the use of compound of general formula 1 for the treatment of malignancy by inhibition of PI3-Akt pathway and or induction of NO. The present invention further relates to a method of treating malignancy by inhibition of PI3-Akt pathway and or induction of NO by administration of compound or said composition to a mammal in need thereof.
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(2010/08/04)
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- Synthesis of new potential chelating agents: Catechol-bisphosphonate conjugates for metal intoxication therapy
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In a quest for better chelating therapy drugs for the treatment of intoxication by Fe, Al, or actinides, three new series of bisphosphonates conjugated with catechol were synthesized.
- Xu, Guangyu,Yang, Chunhao,Liu, Bo,Wu, Xihan,Xie, Yuyuan
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p. 251 - 257
(2007/10/03)
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- A stabilized formulation of IBX (SIBX) for safe oxidation reactions including a new oxidative demethylation of phenolic methyl aryl ethers
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(Matrix presented) SIBX is a nonexplosive formulation of IBX that can be used as a suspension in a variety of standard organic solvents such as refluxing EtOAc and THF to oxidize safely alcohols into aldehydes and ketones. The use of hot THF is limited to the oxidation of allylic and benzylic alcohols. Most yields are comparable to those obtained with IBX or DMP. SIBX can also be used to perform oxygenative demethylation of 2-methoxyarenols into orthoquinones and catechols.
- Ozanne, Aurelie,Pouysegu, Laurent,Depernet, Dominique,Francois, Bruno,Quideau, Stephane
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p. 2903 - 2906
(2007/10/03)
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- Process for synthesis of 5-alkylbenzodioxoles
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The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, comprising the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.
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- Process for the synthesis of 5-allybenzodioxoles
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The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, consisting in the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.
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- Substrate selective catalysis by rhodium metallohosts
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A novel supramolecular catalyst functioning according to the principles of enzymatic catalysis is described. It consists of a basket-shaped molecule to which a catalytically active Rh(I) complex is attached. The catalyst selectively hydrogenates and isomerizes allyl-substituted dihydroxyarene substrates that are bound in its cavity. The reactivity of this supramolecular catalyst and its affinity for several substrates is compared with that of the corresponding catalyst without a binding site. Features known from enzymatic catalysis, e.g. Michaelis-Menten kinetics and rate enhancement by cooperative binding, are described and discussed.
- Coolen, Hein K. A. C.,Meeuwis, Johannes A. M.,Van Leeuwen, Piet W. N. M.,Nolte, Roeland J. M.
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p. 11906 - 11913
(2007/10/03)
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- Catechol diacetate derivatives for inducing the production of nerve growth factor to treat degenerative diseases in the central nervous system
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A pharmaceutical composition for the treatment of regressive disorders of the central nervous system treatable by inducing the production and secretion of nerve growth factor, containing as an active ingredient a catechol derivative of the formula STR1 where R6 is a lower alkyl group having 2 to 5 carbon atoms. The catechol derivatives provide preventative and remedial effects for regressive disorders in the central nervous system including senile dementia of the alzheimer type.
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- Hair dyeing composition containing an aryldiamine and a substituted catechol
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A composition for use in the dyeing of keratinous fibre such as hair includes an aqueous anaerobic solution of an aryldiamine and a substituted catechol. Optionally, an aromatic coupling agent can also be incorporated in the composition to modify the shade of color produced. Anaerobic storage conditions can, for example, be maintained by packing the composition in an aerosol container with a halocarbon propellant.
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- Selective Demethylenation and Dimerisation of Compounds Containing Methylenedioxyphenyl Group by Boron Trifluoride-Etherate
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Compounds containing methylenedioxyphenyl group undergo selective benzo-1,3-dioxole ring opening with BF3-etherate.The methylene group thus formed can cause dimerisation of the unchanged or other activated molecules present in the reaction mixture.The reaction is of a general nature.
- Tomar, S. S.,Walia, Suresh,Mukerjee, S. K.
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p. 792 - 793
(2007/10/02)
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