- CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions
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Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
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- Metallo-supramolecular polymer engineered porous carbon framework encapsulated stable ultra-small nanoparticles: A general approach to construct highly dispersed catalysts
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The development of a general approach for fabricating stable ultra-small heterogeneous nanocatalysts has been intensively pursued. However, issues related to complex synthesis processes and structural stability have restricted their investigation and application. Here we report a facile organometallic conjunction strategy for the large-scale fabrication of porous carbon framework encapsulated highly dispersed sub-3 nm ultra-small nanoparticles (USMNPs@PCF). This methodology is based on the convenient aldol condensation reaction to manufacture a metallo-supramolecular polymer precursor and then consequent annealing to form the target nanocomposite. This technique was successfully applied to the preparation of varieties of USMNPs@PCF, including Fe, Co, Ni, Mo, Ru, Rh, Pd and Pt. As a representative application, the PCF encapsulated sub-3 nm Pd nanoparticles demonstrated remarkable durability and efficiency for chemoselective hydrogenation of nitroarenes to their corresponding anilines under ambient conditions with low catalyst loading. All hydrogenation reactions can complete in 4 min with >99% conversion and >99% chemoselectivity. The turnover frequency (TOF) was up to 11:400 h-1 for p-nitrophenol. This work provides a general, scalable and economical route for the manufacture of sub-3 nm and highly dispersed nanocomposites, which can be used in many other important fields, such as electrochemistry, energy science and environmental protection.
- Ai, Yongjian,He, Mengqi,Zhang, Feng,Long, Yang,Li, Yunzheng,Han, Qiang,Ding, Mingyu,Sun, Hong-Bin,Liang, Qionglin
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- Porous silica-encapsulated and magnetically recoverable Rh NPs: A highly efficient, stable and green catalyst for catalytic transfer hydrogenation with "slow-release" of stoichiometric hydrazine in water
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A core-shell structured nanocatalyst (Fe3O4@SiO2-NH2-RhNPs@mSiO2) that is encapsulated with porous silica has been designed and prepared for catalyzing the transfer hydrogenation of nitro compounds into corresponding amines. Rh nanoparticles serve as the activity center, and the porous silica shell plays an important role in the "slow-release" of the hydrogen source hydrazine. This reaction can be carried out smoothly in the green solvent water, and the atom economy can be improved by decreasing the amount of hydrazine hydrate used to a stoichiometric 1.5 equivalent of the substrate. Significantly, high catalytic efficiency is obtained and the turnover frequency (TOF) can be up to 4373 h-1 in the reduction of p-nitrophenol (4-NP). A kinetics study shows that the order of reaction is ~0.5 towards 4-NP, and the apparent active energy Ea is 58.18 kJ mol-1, which also gives evidence of the high catalytic efficiency. Additionally, the excellent stability of the catalyst has been verified after 15 cycles without any loss of catalytic activity, and it is easily recovered by a magnet after reaction due to the Fe3O4 nucleus.
- Zhou, Junjie,Li, Yunong,Sun, Hong-Bin,Tang, Zhike,Qi, Li,Liu, Lei,Ai, Yongjian,Li, Shuang,Shao, Zixing,Liang, Qionglin
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- Ultrafine FeCu Alloy Nanoparticles Magnetically Immobilized in Amine-Rich Silica Spheres for Dehalogenation-Proof Hydrogenation of Nitroarenes
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A novel core–shell structured nanocatalyst (Fe3O4@SiO2-NH2-FeCu nanoparticles) with ultrafine FeCu alloy NPs magnetically immobilized in porous silica has been fabricated. The obtained catalyst revealed excellent activity and chemoselectivity for catalyzing the hydrogenation of nitroarenes to corresponding anilines using hydrazine hydrate as the hydrogen source, and the reaction could be carried out smoothly in water, which is an environmentally friendly solvent. The FeCu alloy effectively prevented the dehalogenation of halonitroarenes, and X-ray photoelectron spectroscopy (XPS) study showed that it resulted from the electron-enrichment of Fe from Cu. A kinetics study indicated that the reaction order was about 1.5 towards 4-CNB and the apparent active energy (Ea) was 48.1 kJ mol?1, which is a relatively low value. Furthermore, the FeCu NPs are magnetically immobilized in the silica spheres (Fe3O4@SiO2), therefore the catalyst can be easily recovered by use of an external magnet and also possesses a long life time.
- Bao, Hongjie,Li, Yunong,Liu, Lei,Ai, Yongjian,Zhou, Junjie,Qi, Li,Jiang, Ruihang,Hu, Zenan,Wang, Jingting,Sun, Hongbin,Liang, Qionglin
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- Salicylanilides Reduce SARS-CoV-2 Replication and Suppress Induction of Inflammatory Cytokines in a Rodent Model
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SARS-CoV-2 virus has recently given rise to the current COVID-19 pandemic where infected individuals can range from being asymptomatic, yet highly contagious, to dying from acute respiratory distress syndrome. Although the world has mobilized to create antiviral vaccines and therapeutics to combat the scourge, their long-term efficacy remains in question especially with the emergence of new variants. In this work, we exploit a class of compounds that has previously shown success against various viruses. A salicylanilide library was first screened in a SARS-CoV-2 activity assay in Vero cells. The most efficacious derivative was further evaluated in a prophylactic mouse model of SARS-CoV-2 infection unveiling a salicylanilide that can reduce viral loads, modulate key cytokines, and mitigate severe weight loss involved in COVID-19 infections. The combination of anti-SARS-CoV-2 activity, cytokine inhibitory activity, and a previously established favorable pharmacokinetic profile for the lead salicylanilide renders salicylanilides in general as promising therapeutics for COVID-19.
- Beutler, Nathan,Blake, Steven,Eubanks, Lisa M.,Janda, Kim D.,Ji, Henry,Manning, John T.,Maruyama, Junki,Paessler, Slobodan,Shaabani, Namir,Teijaro, John R.
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p. 2229 - 2237
(2021/08/24)
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- Salicylanilide Analog Minimizes Relapse of Clostridioides difficile Infection in Mice
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Clostridioides difficile infection (CDI) causes serious and sometimes fatal symptoms like diarrhea and pseudomembranous colitis. Although antibiotics for CDI exist, they are either expensive or cause recurrence of the infection due to their altering the colonic microbiota, which is necessary to suppress the infection. Here, we leverage a class of known membrane-targeting compounds that we previously showed to have broad inhibitory activity across multiple Clostridioides difficile strains while preserving the microbiome to develop an efficacious agent. A new series of salicylanilides was synthesized, and the most potent analog was selected through an in vitro inhibitory assay to evaluate its pharmacokinetic parameters and potency in a CDI mouse model. The results revealed reduced recurrence of CDI and diminished disturbance of the microbiota in mice compared to standard-of-care vancomycin, thus paving the way for novel therapy that can potentially target the cell membrane of C. difficile to minimize relapse in the recovering patient.
- Blake, Steven,Thanissery, Rajani,Rivera, Alissa J.,Hixon, Mark S.,Lin, Mingliang,Theriot, Casey M.,Janda, Kim D.
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p. 6898 - 6908
(2020/07/28)
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- Novel Deazaflavin Analogues Potently Inhibited Tyrosyl DNA Phosphodiesterase 2 (TDP2) and Strongly Sensitized Cancer Cells toward Treatment with Topoisomerase II (TOP2) Poison Etoposide
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Topoisomerase II (TOP2) poisons as anticancer drugs work by trapping TOP2 cleavage complexes (TOP2cc) to generate DNA damage. Repair of such damage by tyrosyl DNA phosphodiesterase 2 (TDP2) could render cancer cells resistant to TOP2 poisons. Inhibiting TDP2, thus, represents an attractive mechanism-based chemosensitization approach. Currently known TDP2 inhibitors lack cellular potency and/or permeability. We report herein two novel subtypes of the deazaflavin TDP2 inhibitor core. By introducing an additional phenyl ring to the N-10 phenyl ring (subtype 11) or to the N-3 site of the deazaflavin scaffold (subtype 12), we have generated novel analogues with considerably improved biochemical potency and/or permeability. Importantly, many analogues of both subtypes, particularly compounds 11a, 11e, 12a, 12b, and 12h, exhibited much stronger cancer cell sensitizing effect than the best previous analogue 4a toward the treatment with etoposide, suggesting that these analogues could serve as effective cellular probes.
- Kankanala, Jayakanth,Ribeiro, Carlos J. A.,Kiselev, Evgeny,Ravji, Azhar,Williams, Jessica,Xie, Jiashu,Aihara, Hideki,Pommier, Yves,Wang, Zhengqiang
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p. 4669 - 4682
(2019/05/17)
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- Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes
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Control of chemoselectivity is a special challenge for the reduction of nitroarenes bearing one or more unsaturated groups. Here, we report a flower-like Rh/α-FeOOH catalyst for the chemoselective hydrogenation of nitrostyrene to vinylaniline over full conversion, which benefits the new functionalized aminostyrene because the multisubstituted aminostyrenes are usually commercially unavailable. This catalyst does not only show desirable selectivity for the vinylanilines, but also exhibits the inertness to various other reducible groups over wide reaction duration. The catalytic selectivity for the reduction of the nitro group towards vinyl group was investigated by the control experiments and FT-IR analysis. We have found that the abundant hydroxyl groups in the α-FeOOH may contribute to the improvement of catalytic activity and selectivity. Furthermore, the catalyst exhibits excellent stability and keeps its catalytic performance even after 6 cycles. (Figure presented.).
- Hu, Zenan,Ai, Yongjian,Liu, Lei,Zhou, Junjie,Zhang, Gang,Liu, Hongqi,Liu, Xiangyu,Liu, Zhibo,Hu, Jianshe,Sun, Hong-bin,Liang, Qionglin
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supporting information
p. 3146 - 3154
(2019/05/10)
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- Synthesis, SAR and molecular docking study of novel non-β-lactam inhibitors of TEM type β-lactamase
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The novel classes of acylated phenoxyanilide and thiourea compounds were investigated for their ability to inhibit TEM type β-lactamase enzyme. Two compounds 4g and 5c reveal the inhibition potency in micromolar range and show their action by non-covalent binding in the vicinity of the TEM-171 active site. The structure activity relationship around carbon chain length and different substituents in ortho- and para-positions of acylated phenoxyanilide as well as molecular modelling study has been performed.
- Antipin, Roman L.,Beshnova, Daria A.,Petrov, Rostislav A.,Shiryaeva, Anna S.,Andreeva, Irina P.,Grigorenko, Vitaly G.,Rubtsova, Maya Yu.,Majouga, Alexander G.,Lamzin, Victor S.,Egorov, Alexey M.
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p. 1588 - 1592
(2017/03/17)
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- Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein
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Structure-based drug design was utilized to develop novel, 1-hydroxy-2-naphthoate-based small-molecule inhibitors of Mcl-1. Ligand design was driven by exploiting a salt bridge with R263 and interactions with the p2 pocket of the protein. Significantly, target molecules were accessed in just two synthetic steps, suggesting further optimization will require minimal synthetic effort. Molecular modeling using the Site-Identification by Ligand Competitive Saturation (SILCS) approach was used to qualitatively direct ligand design as well as develop quantitative models for inhibitor binding affinity to Mcl-1 and the Bcl-2 relative Bcl-xL as well as for the specificity of binding to the two proteins. Results indicated hydrophobic interactions in the p2 pocket dominated affinity of the most favourable binding ligand (3bl: Ki = 31 nM). Compounds were up to 19-fold selective for Mcl-1 over Bcl-xL. Selectivity of the inhibitors was driven by interactions with the deeper p2 pocket in Mcl-1 versus Bcl-xL. The SILCS-based SAR of the present compounds represents the foundation for the development of Mcl-1 specific inhibitors with the potential to treat a wide range of solid tumours and hematological cancers, including acute myeloid leukemia.
- Lanning, Maryanna E.,Yu, Wenbo,Yap, Jeremy L.,Chauhan, Jay,Chen, Lijia,Whiting, Ellis,Pidugu, Lakshmi S.,Atkinson, Tyler,Bailey, Hala,Li, Willy,Roth, Braden M.,Hynicka, Lauren,Chesko, Kirsty,Toth, Eric A.,Shapiro, Paul,MacKerell, Alexander D.,Wilder, Paul T.,Fletcher, Steven
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p. 273 - 292
(2016/03/22)
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- Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors
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Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is
- Yang, Liuqing,Liu, Wei,Mei, Hanbing,Zhang, Yuan,Yu, Xiaojuan,Xu, Yufang,Li, Honglin,Huang, Jin,Zhao, Zhenjiang
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p. 671 - 676
(2015/04/27)
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- ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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Disclosed are compounds of Formula (I), and salts thereof, wherein R1, RA2, RA3 and RA4, are defined herein, which have properties for positive allosteric modulation of mGluR-4 receptor sites. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating Parkinson's disease and related disorders using the same.
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- ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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Formula (I), and salts thereof, wherein R1, RA2, RA3 and RA4, are defined herein, which have properties for positive allosteric modulation of mGluR-4 receptor sites. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating Parkinson's disease and related disorders using the same.
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- Quinolin-4(1 H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria
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We present a novel series of quinolin-4(1H)-imines as dual-stage antiplasmodials, several-fold more active than primaquine in vitro against Plasmodium berghei liver stage. Among those, compounds 5g and 5k presented low nanomolar IC50 values. The compounds are metabolically stable and modulate several drug targets. These results emphasize the value of quinolin-4(1H)-imines as a new chemotype and their suitable properties for further drug development.
- Rodrigues, Tiago,Da Cruz, Filipa P.,Lafuente-Monasterio, Maria J.,Gon?alves, Daniel,Ressurrei??o, Ana S.,Sitoe, Ana R.,Bronze, Maria R.,Gut, Jiri,Schneider, Gisbert,Mota, Maria M.,Rosenthal, Philip J.,Prude?ncio, Miguel,Gamo, Francisco-Javier,Lopes, Francisca,Moreira, Rui
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p. 4811 - 4815
(2013/07/19)
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- Discovery of novel and potent aryl diamines as leukotriene A4 hydrolase inhibitors
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The synthesis and biological evaluation of a series of aryl diamines as inhibitors of LTA4-h inhibitors are described. The optimization which led to the identification of the optimal para-substitution on the diphenyl ether moiety and diamine spacer is discussed. The resulting compounds such as 3l have excellent enzyme and cellular potency as well as desirable pharmacokinetic properties.
- Khim, Seock-Kyu,Bauman, John,Evans, Jarred,Freeman, Beverly,King, Beverly,Kirkland, Thomas,Kochanny, Monica,Lentz, Dao,Liang, Amy,Mendoza, Lisa,Phillips, Gary,Tseng, Jih-Lie,Wei, Robert G.,Ye, Hong,Yu, Limei,Parkinson, John,Guilford, William J.
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scheme or table
p. 3895 - 3898
(2009/04/07)
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- Inhibitors of protein kinases
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Compounds that inhibit protein kinases, compositions containing the compounds and methods of treating diseases using the compounds are disclosed.
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Page/Page column 19
(2010/11/27)
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- Novel glycine transporter type-2 reuptake inhibitors. Part 1: α-amino acid derivatives
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A variety of α-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [ 14C]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) was evaluated. An array of substituents at the chiral center was studied and overall, L-phenylalanine was identified as the preferred amino acid residue. Compounds prepared from L-amino acids were more potent GlyT-2 inhibitors than analogs derived from the corresponding D-amino acids. Introducing an achiral amino acid such as glycine, or incorporating geminal substitution in the α-position, led to a significant reduction in GlyT-2 inhibitory properties.
- Wolin, Ronald L.,Venkatesan, Hariharan,Tang, Liu,Santillán Jr., Alejandro,Barclay, Tristin,Wilson, Sandy,Lee, Doo Hyun,Lovenberg, Timothy W.
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p. 4477 - 4492
(2007/10/03)
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- Phenoxyphenyl sulfone N-formylhydroxylamines (Retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors
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A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1′ substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a.highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.
- Wada,Holms,Curtin,Dai,Florjancic,Garland,Guo,Heyman,Stacey,Steinman,Albert,Bouska,Elmore,Goodfellow,Marcotte,Tapang,Morgan,Michaelides,Davidsen
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p. 219 - 232
(2007/10/03)
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- 3-cycloalkyl-prop-2-enamides
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A compound selected from the group consisting of a compound of the formula STR1 wherein R1 is hydrogen or alkyl of 1 to 3 carbon atoms, W is selected from the group consisting of --O--, --S--, --SO-- and --SO2 --, Z and Y are --CH-- or one is --CH-- and the other is --N--, R2, R3, R4, R5 and R6 are individually selected from the group consisting of hydrogen, halogen, methoxy, methylthio, alkyl of 1 to 4 carbon atoms, --WCF3, --CF3, --NO2, --CN--, --W--(CH2)n --CF3, --W--(CF2)n --CF3, --(CF2)n --CF3 and --(CH2)n --CX3, is an integer from 1 to 3, X is a halogen or R3 and R4 together are --O--(CH2)--O-- and R2, R5 and R6 are as defined above, R7 and R8 are individually hydrogen or alkyl of 1 to 6 carbon atoms, R9 is cycloalkyl of 3 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable salts with bases.
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- Phenylcarboxylic acid derivatives
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Phenylcarboxylic acid derivatives having the formula: STR1 wherein R1 and R2 are each H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, --O--D--R5 (D is alkylene, R5 is H, amino, morpholino, carboxyl, phthalimido, phenyl, epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl, or both form alkylenedioxy; R3 is H, --E--R6 (E is alkylene, R6 is H, carboxyl, cyano, OH, phenylalkoxy, or halogen-substituted phenyl, or phenylcarbamoyl), --CO--G--R7 (G is alkylene, R7 is H, substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl, or halophenyl; R4 is H or alkyl; A is alkylene, alkylene condensed with cycloalkyl ring, or alkenylene; B is alkylene or alkenylene; l is 0 or 1. Said compounds have fatty acid synthesis-inhibitory activity, cholesterol synthesis-inhibitory activity and are useful as antilipidemic agent, prophylactic and treating agent of artherosclerosis, prophylactic and treating agent of obesity, antidiabetics.
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- Glycosides of N-Hydroxy-N-arylamine Derivatives. Part 3. Kinetic and Mechanistic Studies on the Degradation Reaction of O-Glycosides of N-Hydroxy-N-arylamines and their Acetohydroxamic Acids in Acidic and Alkaline Media
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Good first-order kinetics of the degradation reaction of 1--1-deoxy-β-D-glucopyranoses (1a-d), 1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose (2a) and sodium 1--1-deoxy-β-D-glucopyranuronate (3a) in aqueous acidic solutions have been observed.Compounds (1a-d) and (3a) were fairly stable in neutral solution, but in aqueous acidic solutions at 20 deg C these compounds decomposed to the corresponding arylamino derivatives (4a-d) and D-gluconic acid (5) .The compound (2a) decomposed ca. 7400 times faster than compound (1a) to the same products (4a) and (5) in the same conditions.In an alkaline solution, compounds (1a)-(3a) gave the corresponding azoxybenzene.In the acid-catalysed redox degradation reaction, the hydrolysis of the N-acetyl group of compounds (1a-d) and (3a) is considered to be the rate-determining step.The effects of pH and additives on the reaction rate are reported.The mechanism of the acid-catalysed redox fission of the N-O linkage in the above O-glycosides is discussed.
- Yoshioka, Tadao,Uematsu, Takayoshi
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p. 1377 - 1382
(2007/10/02)
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- Sulphur- and oxygen-containing diaryl compounds
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The sulphur- and oxygen-containing diaryl compounds of the formula: STR1 in which A and B, which may be the same or different, represent O, S, SO or SO2, Alk is a C1 -C4 hydrocarbon radical with a straight or branched chain, R represents COOH, an esterified COOH group, a carboxylic amide group, OH, O-SO2 CH3, NH2, NHR1, NR1 R2, NHZOH, NHZNR1 R2, C(=NH)NH2, C(=NH)NHOH or 2-Δ2 -imidazolinyl, Z is a C2 -C4 hydrocarbon radical with a straight or branched chain, and R1 and R2 each represent a C1 -C3 lower alkyl group, or together form, with the nitrogen atom to which they are linked, a N-heterocyclic group of 5 to 7 ring atoms which can be substituted and can comprise a second hetero-atom, and their addition salts with bases when R is COOH, and their addition salts with acids when R is a basic radical, are useful pharmacological agents in the treatment of circulatory complaints such as cardio-vascular illnesses.
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