- A novel three-component reaction toward dihydrooxazolopyridines
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Isocyano dihydropyridones accessible via a recently reported multicomponent reaction react with aldehydes and amines to afford dihydrooxazolopyridines in high yield. The scope and limitations of this novel multicomponent reaction were investigated. The ef
- Scheffelaar, Rachel,Paravidino, Monica,Muilwijk, Daan,Lutz, Martin,Spek, Anthony L.,De Kanter, Frans J. J.,Orru, Romano V. A.,Ruijter, Eelco
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Read Online
- Selenoxide elimination triggers enamine hydrolysis to primary and secondary amines: A combined experimental and theoretical investigation
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We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).
- Bortoli, Marco,Gianoncelli, Alessandra,Ongaro, Alberto,Orian, Laura,Oselladore, Erika,Ribaudo, Giovanni,Zagotto, Giuseppe
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- Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
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The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
- Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
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supporting information
p. 6207 - 6227
(2021/05/06)
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- Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
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Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.
- Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong
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p. 2059 - 2067
(2021/09/02)
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- Half-sandwiched ruthenium complex containing carborane schiff base ligand and preparation and application thereof
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The invention relates to a half-sandwiched ruthenium complex containing a carborane schiff base ligand and a preparation and an application thereof. The preparation method specifically comprises the following steps; i) dissolving o-carborane formaldehyde and aromatic amine in an organic solvent, carrying out reaction at 60-100 DEG C for 8-12h, cooling to room temperature after the reaction; ii) adding n-butyllithium, carrying out reaction at room temperature for 1.5-2.5h; ii) adding phellandrene ruthenium chloride dimer, carrying out reaction at room temperature for 3-6h, and obtaining the half-sandwiched ruthenium complex through separation. The half-sandwiched ruthenium complex is applied to catalyze transfer hydrogenation reaction of nitrile compounds. Compared with the prior art, the complex of the present invention is not sensitive to air and water, has stable properties, and shows high-efficiency catalytic activity in catalyzing the transfer hydrogenation reaction of nitrile compounds. The preparation method of the complex is simple and green, high in yield, mild in reaction conditions and good in universality.
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Paragraph 0067-0071
(2020/12/09)
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- Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions
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The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).
- Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.
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supporting information
(2020/07/15)
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- Locking the Dynamic Axial Chirality of Biphenyl Crown Ethers through Threading
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This paper describes the syntheses of [2]rotaxanes comprising 23- and 26-membered biphenyl crown ethers as the macrocyclic components and secondary ammonium ions as the dumbbell-shaped components, and the locking of the dynamic axial chirality of the biph
- Kimura, Tomoya,Miyagawa, Shinobu,Takaya, Hikaru,Naito, Masaya,Tokunaga, Yuji
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p. 3897 - 3903
(2020/10/28)
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- Platinum-(phosphinito-phosphinous acid) complexes as bi-talented catalysts for oxidative fragmentation of piperidinols: An entry to primary amines
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Platinum-(phosphinito-phosphinous acid) complex catalyzes the oxidative fragmentation of hindered piperidinols according to a hydrogen transfer induced methodology. This catalyst acts successively as both a hydrogen carrier and soft Lewis acid in a one pot-two steps process. This method can be applied to the synthesis of a wide variety of primary amines in a pure form by a simple acid-base extraction without further purification.
- Membrat, Romain,Vasseur, Alexandre,Moraleda, Delphine,Michaud-Chevallier, Sabine,Martinez, Alexandre,Giordano, Laurent,Nuel, Didier
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p. 37825 - 37829
(2019/12/03)
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- Nano-Fe3O4@SiO2-SO3H: A magnetic, reusable solid-acid catalyst for solvent-free reduction of oximes to amines with the NaBH3CN/ZrCl4 system
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In this study, the immobilization of sulfonic acid on silica-layered magnetite was carried out by the reaction of ClSO3H with silica-layered magnetite. The prepared magnetic nanoparticles of Fe3O4@SiO2-SO3H were then characterized using scanning electron microscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, Fourier transform infrared spectroscopy, vibrating sample magnetometry, and transmission electron microscopy. The sulfonated nanocomposite exhibited excellent catalytic activity and reusability in the reduction of various aldoximes and ketoximes with NaBH3CN in the presence of ZrCl4. All reactions were carried out under solvent-free conditions (r.t. or 75–80°C) within 3–70 min to afford amines in high to excellent yields.
- Sadighnia, Leila,Zeynizadeh, Behzad,Karami, Shiva,Abdollahi, Mohammad
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p. 535 - 542
(2019/01/04)
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- Compound and application thereof in resistance to arenavirus infection
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The invention provides a compound and application thereof in resistance to arenavirus infection. The structural formula of the compound is as shown in the figure (I) in the specification, wherein Ar is selected from an aromatic ring or aromatic heterocyct
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- A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin
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Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.
- Suthagar, Kajitha,Fairbanks, Antony J.
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supporting information
p. 713 - 715
(2017/01/13)
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- BENZAZEPINE DICARBOXAMIDE COMPOUNDS WITH TERTIARY AMIDE FUNCTION
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This invention relates to new benzazepine dicarboxamide compounds of the formula (I) wherein R1 to R 3 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.
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Page/Page column 50
(2017/12/29)
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- Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor
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The invention relates to a novel sulfonamide compound in a structure of a general formula I as shown in the specification, or pharmaceutically acceptable salt and a preparation method of the novel sulfonamide compound, and further relates to a drug composition containing the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound, and a use of the compound or the pharmaceutically acceptable salt for preparing a drug for preventing and/or treating symptoms or diseases such as hyperglycemia and diabetes mellitus type 2 since the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound has activity of inhibiting a protein tyrosine phosphatase 1B (PTP 1B).
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- 3. 4 - diphenyl - 4H - 1, 2, 4 - triazole derivative and its preparation method and application (by machine translation)
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The invention discloses 3, 4 - diphenyl - 4H - 1, 2, 4 - triazole derivative and its preparation method and application. In particular, the invention relates to the formula (I) structure of 3, 4 - diphenyl - 4H - 1, 2, 4 - triazole derivatives, its stereoisomers or its pharmaceutically acceptable salt, formula (I) in the definition of each substituent is as defined in the specification. These structure of novel compound with heat shock protein HSP90 inhibitory activity, can be used for treating cancer, neurodegenerative diseases, inflammatory diseases, autoimmune diseases, ischemic brain injury and the like, it has broad application prospects. (by machine translation)
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- Stereoelectronic effects in the reaction of aromatic substrates catalysed by: Halomonas elongata transaminase and its mutants
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A transaminase from Halomonas elongata and four mutants generated by an in silico-based design were recombinantly produced in E. coli, purified and applied to the amination of mono-substituted aromatic carbonyl-derivatives. While benzaldehyde derivatives were excellent substrates, only NO2-acetophenones were transformed into the (S)-amine with a high enantioselectivity. The different behaviour of wild-type and mutated transaminases was assessed by in silico substrate binding mode studies.
- Contente, Martina Letizia,Planchestainer, Matteo,Molinari, Francesco,Paradisi, Francesca
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p. 9306 - 9311
(2016/10/13)
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- One-pot reductive amination of carbonyl compounds with ammonia via ‘hydrogen borrowing’ using hydrido- and bis-ammine P,O(Me)-ruthenacycles
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The novel cationic [RuH{PPh2(2-OMeC6H4)}2]BPh4and neutral trans-[Ru(NH3)2{PPh2(2-OC6H4)}2] complexes were isolated from phosphine substitution reactions with [RuH(1,5-cod)(NH2NMe2)3]BPh4and [RuCl(1,5-cod)(NH3)2(NH2NMe2)]BPh4respectively. Ligand induced bisdemethylation of the pendent ether moieties of the phosphines occurred to give rise to the bis-phosphanylphenoxy moieties. Both complexes catalyzed the one-pot reductive amination of carbonyl compounds where excellent selectivity of aryl aldehydes over aryl ketones as precursors to the alcoholic species existed. Through substrate screening and1H NMR studies, both steric and electronic effects of the substrates were found to influence the hydrogenation/amination mechanistic pathway, as well as direct the alcohol:amine selectivity.
- Malan, Frederick P.,Noh, Ji-Hyang,Naganagowda, Gadada,Singleton, Eric,Meijboom, Reinout
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p. 139 - 145
(2016/11/18)
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- Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: An environmentally friendly approach
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A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al2O3, and reaction conditions, a very high selectivity of furfurylamine (~92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.
- Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime
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supporting information
p. 487 - 496
(2016/01/30)
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- Characterization of a selective inverse agonist for estrogen related receptor α as a potential agent for breast cancer
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The estrogen-related receptor α (ERRα) is an orphan nuclear receptor that plays a primary role in the regulation of cellular energy homeostasis and osteogenesis. It is reported that ERRα is widely expressed in a range of tissues and accumulating evidence has supported that the high expression of ERRα correlates with poor prognosis of various human malignancies, including breast, endometrium, colon, prostate and ovary cancers. Herein is described the discovery of a novel selective inverse agonist (HSP1604) of ERRα, but not of ERRβ and ERRγ, as determined using transient transfection luciferase reporter assay and a time-resolved fluorescence resonance energy transfer (TR-FRET) co-activator assay. HSP1604 potently inhibits ERRα transcriptional activity with IC50=1.47±0.17?μM in cell-based luciferase reporter assay and also decreases the protein level of ERRα and the mRNA levels of its downstream target genes such as pyruvate dehydrogenase kinase 4 (PDK4), pS2 and osteopontin. HSP1604 has also suppressed the proliferation of different human cancer cell lines and the migration of breast cancer cells with high expression of ERRα. Representative in vivo results show that HSP1604 suppresses the growth of human breast cancer xenograft in nude mice as doses at 30?mg/kg or 100?mg/kg administered every other day during 28-day period. HSP1604 thus has the potential both as a new agent to inhibit the growth of tumors and as a chemical probe of ERRα biology.
- Zhang, Liudi,Liu, Peihong,Chen, Haifei,Li, Qunyi,Chen, Lu,Qi, Huijie,Shi, Xiaojin,Du, Yongli
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p. 439 - 448
(2016/08/17)
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- Ruthenium(II) 9,10-phenanthrenequinone thiosemicarbazone complexes: Synthesis, characterization, and catalytic activity towards the reduction as well as condensation of nitriles
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The ligands 9,10-phenanthrenequinone-N4-substituted thiosemicarbazones (HL1-3) and their ruthenium(II) complexes were synthesized and characterized by elemental and spectroscopic methods. The ligands are tridentate, monobasic chelating ligands with O, N, and S as the donor sites and are in the thiol form in all the complexes. Catalytic studies showed that all the complexes displayed good catalytic activity towards the reduction of nitriles and also the condensation of nitriles with 2-aminoalcohol under solvent-free conditions.
- Anitha, Panneerselvam,Viswanathamurthi, Periasamy,Kesavan, Devarayan,Butcher, Ray Jay
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p. 321 - 334
(2015/10/20)
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- Meso-Methylhydroxy BODIPY: A scaffold for photo-labile protecting groups
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Here, we show that by installing a meso-methylhydroxy moiety, the boron dipyrromethene (BODIPY) scaffold can be converted into an efficient caging group, removable by green light. We describe caging and uncaging of important chemical functionalities and demonstrate green light mediated control over biological processes in cultured cell lines and neurons. This journal is
- Rubinstein, Naama,Liu, Pei,Miller, Evan W.,Weinstain, Roy
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supporting information
p. 6369 - 6372
(2015/04/14)
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- Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic
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Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated IRβ phosphorylation and insulin-stimulated glucose uptake.
- Liu, Peihong,Du, Yongli,Song, Lianhua,Shen, Jingkang,Li, Qunyi
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p. 7079 - 7088
(2015/11/11)
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- The efficient solvent-free reduction of oximes to amines with NaBH3CN catalyzed by ZrCl4/nano Fe3O4 system
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Reduction of various aldoximes and ketoximes to the corresponding amines was carried out easily and efficiently with NaBH3CN in the presence of ZrCl4/nano Fe3O4 system. The reactions were carried out under solvent-free conditions at room temperature or 75-80°C to afford amines in high to excellent yields.
- Sadighnia, Leila,Zeynizadeh, Behzad
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p. 873 - 878
(2015/03/18)
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- An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
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A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
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p. 34764 - 34767
(2014/11/08)
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- Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides
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A transition metal-free process, promoted by sodium borohydride, has been developed for convenient and selective hydration of nitriles to corresponding amides. The present process converts the aromatic, aliphatic, and heteroaromatic nitriles with wide functional group tolerance. The regioselective hydration of one nitrile moiety in the presence of an other nitrile group makes high impact in the present protocol.
- Verma, Praveen Kumar,Kumar, Neeraj,Sharma, Upendra,Bala, Manju,Kumar, Vishal,Singh, Bikram
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p. 2867 - 2875
(2013/09/02)
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- Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseas
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- ARYL OR N-HETEROARYL SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives of Formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands of formula (I), to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and
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- AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to amine substituted methanesulfonamide derivatives of formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (R) bearing a phenyl moiety substituted with an N-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- Aryl or N-heteroaryl Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- Amine Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to amine substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions
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The rate constants for the reactions of a variety of nucleophiles reacting with substituted benzyl chlorides in liquid ammonia (LNH3) have been determined. To fully interpret the associated linear free-energy relationships, the ionization constants of phenols ions in liquid ammonia were obtained using UV spectra. These equilibrium constants are the product of those for ion-pair formation and dissociation to the free ions, which can be separated by evaluating the effect of added ammonium ions. There is a linear relationship between the pKa of phenols in liquid ammonia and those in water of slope 1.68. Aminium ions exist in their unprotonated free base form in liquid ammonia and their ionization constants could not be determined by NMR. The rates of solvolysis of substituted benzyl chlorides in liquid ammonia at 25 °C show a Hammett ρ of zero, having little or no dependence upon ring substituents, which is in stark contrast with the hydrolysis rates of substituted benzyl halides in water, which vary 107 fold. The rate of substitution of benzyl chloride by substituted phenoxide ions is first order in the concentration of the nucleophile indicative of a SN2 process, and the dependence of the rate constants on the pKa of the phenol in liquid ammonia generates a Bronsted βnuc = 0.40. Contrary to the solvolysis reaction, the reaction of phenoxide ion with 4-substituted benzyl chlorides gives a Hammett ρ = 1.1, excluding the 4-methoxy derivative, which shows the normal positive deviation. The second order rate constants for the substitution of benzyl chlorides by neutral and anionic amines show a single Bronsted βnuc = 0.21 (based on the aqueous pKa of amine), but their dependence on the substituent in substituted benzyl chlorides varies with a Hammett ρ of 0 for neutral amines, similar to that seen for solvolysis, whereas that for amine anions is 0.93, similar to that seen for phenoxide ion.(Figure Presented)
- Ji, Pengju,Atherton, John,Page, Michael I.
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supporting information; scheme or table
p. 1425 - 1435
(2011/04/23)
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- A new and convenient method for reduction of oximes to amines with NaBH3CN in the presence of MoCl5/NaHSO4? H2O system
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Various aldoximes and ketoximes were efficiently reduced to their corresponding amines with NaBH3CN in the presence of MoCl 5/NaHSO4?H2O system. Reduction reactions were carried out in refluxing EtOH or DMF within 0.3-3.8 h to afford the amines in high to excellent yields.
- Kouhkan, Mehri,Zeynizadeh, Behzad
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experimental part
p. 3323 - 3326
(2012/02/04)
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- A modified Curtius reaction: an efficient and simple method for direct isolation of free amine
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The Curtius rearrangement and related reactions are often used to convert carboxylic acids to the corresponding primary amines. However, this reaction often requires harsh conditions for hydrolysis of the isocyanate intermediates to amines, and can also be contaminated by the formation of corresponding ureas due to the reactive nature of the intermediates. We have discovered that by quenching the isocyanate intermediates with sodium trimethylsilanolate, the free amines can be isolated after aqueous workup. This mild and fast procedure provides free amines in one pot with good yields.
- Ma, Bin,Lee, Wen-Cherng
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experimental part
p. 385 - 386
(2010/03/03)
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- Photoactivatable HNO-releasing compounds using the retro-Diels-Alder reaction
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We synthesized hetero-Diels-Alder cycloadducts from acyl nitroso derivatives and 9,10-dimethylanthracene, to be photo-inducible HNO-releasing agents and found that introduction of conjugated nitroaromatic groups effectively enhanced the responsiveness of HNO release to UV-A irradiation; we confirmed photoinduced HNO formation by EPR and GCMS analysis. The Royal Society of Chemistry.
- Adachi, Yusuke,Nakagawa, Hidehiko,Matsuo, Kazuya,Suzuki, Takayoshi,Miyata, Naoki
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supporting information; experimental part
p. 5149 - 5151
(2009/03/11)
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- Structure-based design and synthesis of the first weak non-phosphate inhibitors for IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis
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In this paper, we describe the structure-based design, synthesis, and biological evaluation of cytosine derivatives and analogues that inhibit IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. This pathway is responsible for the biosynthesis of the C5 precursors to isoprenoids, isopentenyl diphosphate (IPP, 1) and dimethylallyl diphosphate (DMAPP, 2; Scheme 1). The non-mevalonate pathway is the sole source for 1 and 2 in the protozoan Plasmodium parasites. Since mammals exclusively utilize the alternative mevalonate pathway, the enzymes of the non-mevalonate pathway have been identified as attractive new drug targets in the fight against malaria. Based on computer modeling (cf. Figs. 2 and 3), new cytosine derivatives and analogues (Fig. 1) were selected as potential drug-like inhibitors of IspF protein, and synthesized (Schemes 2-5). Determination of the enzyme activity by 13C-NMR spectroscopy in the presence of the new ligands showed inhibitory activities for some of the prepared cytosine and pyridine-2,5-diamine derivatives in the upper micromolar range (IC50 values; Table). The data suggest that it is possible to inhibit IspF protein without binding to the polar diphosphate binding site and the side chain of Asp56′, which interacts with the ribose moiety of the substrate and substrate analogues. Furthermore, a new spacious sub-pocket was discovered which accommodates aromatic spacers between cytosine derivatives or analogues (binding to 'Pocket III') and rings that occupy the flexible hydrophobic region of 'Pocket II'. The proposed binding mode remains to be further validated by X-ray crystallography.
- Baumgartner, Corinne,Eberle, Christian,Diederich, Francois,Lauw, Susan,Rohdich, Felix,Eisenreich, Wolfgang,Bacher, Adelbert
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p. 1043 - 1068
(2008/03/13)
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- Study on the reactions of fluoroalkanesulfonyl azides with cycloalkenyl ether and aryl ynamines
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The reactions of fluoroalkanesulfonyl azides 1 with some electron-rich compounds have been studied in detail. Cycloalkenyl vinyl ethers reacted with 1 readily at 0°C to give the corresponding ring-contraction N-fluoroalkanesulfonyl amidine analogues 3. In
- He, Ping,Zhu, Shizheng
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p. 549 - 555
(2007/10/03)
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- Mechanistic studies on the conversion of arylamines into arylnitro compounds by aminopyrrolnitrin oxygenase: identification of intermediates and kinetic studies
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(Chemical Equation Presented) Rieske business! The Rieske N-oxygenase, aminopyrrolnitrin oxygenase (PrnD), catalyzes the unusual oxidation of arylamines to arylnitro compounds. Kinetic analysis has confirmed that PrnD catalyzes the conversion of the substrate pABA (4-aminobenzylamine) through at least three consecutive reactions: two monooxygenation steps and one dehydrogenation step (see scheme).
- Lee, Jungkul,Zhao, Huimin
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p. 622 - 625
(2007/10/03)
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- The facile preparation of primary and secondary amines via an improved Fukuyama-Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent
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An efficient modification of the Fukuyama-Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved technique was implemented in the synthesis of a complex lipopeptide designed to target α 9β1-integrin proteins predominant on upper airway epithelial cells. The Royal Society of Chemistry 2005.
- Guisado, Cristina,Waterhouse, Jodie E.,Price, Wayne S.,Jorgensen, Michael R.,Miller, Andrew D.
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p. 1049 - 1057
(2007/10/03)
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- First report for the efficient reduction of oximes to amines with zinc borohydride in the form of (Pyridine)(tetrahydroborato)zinc complex
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(Pyridine)(tetrahydroborato)zinc complex, (Py)Zn(BH4) 2, as a stable modification of zinc borohydride can easily reduce a variety of aromatic and aliphaticaldoximes or ketoximes to their corresponding amines in high to excellent yields in refluxing THF.
- Zeynizadeh, Behzad,Zahmatkesh, Karam
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p. 109 - 112
(2007/10/03)
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- Substituted indolines which inhibit receptor tyrosine kinases
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Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.
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Page column 42
(2008/06/13)
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- An efficient chemoselective production of amines from azides using AlCl3/NaBH4
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A practical reagent system AlCl3/NaBH4 is used for the preparation of amines from azides under mild reaction condition, in excellent yields.
- Raja Ram,Purushothama Chary,Salahuddin,Iyengar
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p. 935 - 937
(2007/10/03)
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- Glutaryl Acylases: One-Reaction Enzymes or Versatile Enantioselective Biocatalysts?
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A significant broad substrate specificity, that crosses over the usual β-lactam derivatives, has been observed with an industrial glutaryl-7-aminocephalosporanic acid acylase (GA). This enzyme possesses significant enantioselective amidase and even esterase activity, with a stereopreference for the S-enantiomer. The easy separation of products from unreacted reagents, possessing different physical-chemical properties, is achieved by solvent extraction, avoiding chromatography or distillation during reaction work-up.
- Raimondi, Stefano,Monti, Daniela,Pagnoni, Ugo Maria,Riva, Sergio
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p. 783 - 789
(2007/10/03)
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- SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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- Tricyclic indole-2-carboxylic acids: Highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor
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A series of tricyclic indole-2-carboxylic acid derivatives were synthesized and evaluated by the radioligand binding assay and the anticonvulsant effects in the mouse NMDA-induced seizure model. Among them, derivatives of 3S-(-)-4 such as 3a, 3f, and 3g which had certain zwitterionic anilides showed high affinity to the NMDA-glycine binding site. The absolute configuration of 3S-(-)-4 was confirmed by X-ray crystallographic analysis. In particular, 3g (SM-31900) was found to be a highly active glycine antagonist for both in vitro and in vivo assays (Ki = 1.0 ± 0.1 nM, ED50 = 2.3 mg/kg, iv) and also showed high selectivity for the glycine site. In addition, 3g was soluble enough in aqueous media (> 10 mg/mL at pH 7.4) to use for medications by intravenous injection.
- Katayama, Seiji,Ae, Nobuyuki,Kodo, Toru,Masumoto, Shuji,Hourai, Shinji,Tamamura, Chika,Tanaka, Hiroyasu,Nagata, Ryu
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p. 691 - 701
(2007/10/03)
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- Chemoselective conversion of azides to t-butyl carbamates and amines
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Azides were converted to the corresponding carbamates using a system of 20 mol% of decaborane (B10H14) and 20 weight% of 10% Pd/C in methanol in the presence of di-tert-butyl dicarbonate at rt in high yields and to the corresponding amines using a system of 10 mol% of decaborane and 20 weight% of 10% Pd/C in methanol in the absence of di-tert-butyl dicarbonate at rt in high yields.
- Jung, Yeon Joo,Chang, Yu Mi,Lee, Ji Hee,Yoon, Cheol Min
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p. 8735 - 8739
(2007/10/03)
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- A novel, chemoselective and efficient production of amines from azides using ZrCl4/NaBH4
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A practical and cheaper reagent system ZrCl4/NaBH4 is used for the production of amines from azides is described.
- Purushothama Chary,Raja Ram,Salahuddin,Iyengar
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p. 3559 - 3563
(2007/10/03)
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- A novel and efficient production of amines from azides using LiCl/NaBH4
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A practical and efficient reagent system LiCl/NaBH4 is used for the production of amines from azides is described.
- Raja Ram,Purushothama Chary,Iyengar
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p. 4495 - 4500
(2007/10/03)
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- Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides
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Three 4-arylcarboxamidopyrrolo-2-carboxyanilides bearing different substituents on the pyrrole nitrogen were synthesized and evaluated for their capacities to bind to specific sequences within the minor groove of DNA and to inhibit human topoisomerases I and II in vitro. The cytotoxicity of the drugs correlates with their DNA binding affinities. The two drugs bearing a N-methyl or N-benzyl pyrrole stabilize topoisomerase I-DNA complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Dudouit, Fabienne,Goossens, Jean-Francois,Houssin, Raymond,Henichart, Jean-Pierre,Colson, Pierre,Houssier, Claude,Gelus, Nathalie,Bailly, Christian
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p. 553 - 557
(2007/10/03)
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- Anti-Helicobacter pylori agents. 4. 2-(Substituted guanidino)-4-phenylthiazoles and some structurally rigid derivatives
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In order to find a new class of anti-Helicobacter pylori (H. pylori) agents, a series of 4-[(3-acetamido)phenyl]-2-(substituted guanidino)thiazoles and some structurally rigid analoges were synthesized and evaluated for antimicrobial activity against H. pylori. Among the compounds obtained, high anti-H. pyrori activities were observed in benzyl derivative 34 (MIC = 0.025 μg/mL) and phenethyl derivatives 35 and 36 (MIC = 0.037 μg/mL and 0.017 μg/mL). Though alkyl derivatives generally showed lower activity, the 2-methoxyethyl derivative 28 preserved significant activity (MIC = 0.32 μg/mL) and also exhibited more potent gastric antisecretory activity than ranitidine. Structural restriction by bridging between the thiazole and the phenyl rings with an alkyl chain did not improve the activity in this series.
- Katsura,Tomishi,Inoue,Sakane,Matsumoto,Morinaga,Ishikawa,Takasugi
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p. 3315 - 3321
(2007/10/03)
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