- ELECTROREDUCTION OF 2-OXAZOLINES
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The cathodic behavior of 2-phenyl-4,4-dimethyl-2-oxazoline (4), 2,4,4-trimethyl-2-oxazoline (7) and 2-(1,1-dimethylethyl)-4,4-dimethyl-2-oxazoline (8) at Hg electrodes was investigated.A reduction peak for 4 at -2.49V (SCE), was observed by cyclic voltamm
- Ryan, Christopher M.,Kariv-Miller, Essie
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- A new approach to the synthesis of N-arylakyl aminoalcohols
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N-arylmethyl substituted aminoalcohols were prepared by enantioselective reductive amination of different aromatic and heteroaromatic aldehydes using aminoalcohols and NaBH3CN as a catalyst. The reaction of optically active aminoalcohols afforded optically pure products.
- Leskovsek,Urleb
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- Structure-based drug design of novel potent and selective tetrahydropyrazolo[1,5-a]pyrazines as ATR inhibitors
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A saturation strategy focused on improving the selectivity and physicochemical properties of ATR inhibitor HTS hit 1 led to a novel series of highly potent and selective tetrahydropyrazolo[1,5-a]pyrazines. Use of PI3Kα mutants as ATR crystal structure surrogates was instrumental in providing cocrystal structures to guide the medicinal chemistry designs. Detailed DMPK studies involving cyanide and GSH as trapping agents during microsomal incubations, in addition to deuterium-labeled compounds as mechanistic probes uncovered the molecular basis for the observed CYP3A4 TDI in the series. (Chemical Equation Presented).
- Barsanti, Paul A.,Aversa, Robert J.,Jin, Xianming,Pan, Yue,Lu, Yipin,Elling, Robert,Jain, Rama,Knapp, Mark,Lan, Jiong,Lin, Xiaodong,Rudewicz, Patrick,Sim, Janet,Taricani, Lorena,Thomas, George,Xiao, Linda,Yue, Qin
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Read Online
- Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules
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An efficient catalytic method to convert an α-C-H bond of N-alkylamines into an α-C-alkynyl bond was developed. In the past, such transformations were carried out under oxidative conditions, and the enantioselective variants were confined to tetrahydroisoquinoline derivatives. Here, we disclose a method for the union of N-alkylamines and trimethylsilyl alkynes, without the presence of an external oxidant and promoted through cooperative actions of two Lewis acids, B(C6F5)3 and a Cu-based complex. A variety of propargylamines can be synthesized in high diastereo-and enantioselectivity. The utility of the approach is demonstrated by the late-stage site-selective modification of bioactive amines. Kinetic investigations that shed light on various mechanistic nuances of the catalytic process are presented.
- Chan, Jessica Z.,Yesilcimen, Ahmet,Cao, Min,Zhang, Yuyang,Zhang, Bochao,Wasa, Masayuki
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supporting information
p. 16493 - 16505
(2020/10/26)
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- HETEROARYL(HETEROCYCLYL)METHANOL COMPOUNDS USEFUL IN THE TREATMENT OF HYPERGLYCAEMIA
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There is herein provided a compound of formula I (I) or a pharmaceutically acceptable salt thereof, wherein the ring comprising Q1 to Q5, R1, m, X1 and ring A have meanings as provided in the description.
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Page/Page column 59; 60
(2020/10/09)
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- HETEROCYCLYL(PHENYL)METHANOL COMPOUNDS USEFUL IN THE TREATMENT OF HYPERGLYCAEMIA
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There is herein provided a compound of formula I or a pharmaceutically acceptable salt thereof, wherein X, R1, R2, R3, ring A, n and y have meanings as provided in the description.
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Page/Page column 67-68
(2020/10/09)
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- Microwave-Assisted CuCl-Catalyzed Three-Component Reactions of Alkynes, Aldehydes, and Amino Alcohols
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A microwave (MW)-assisted three-component coupling of amino alcohols, aldehydes, and alkynes is developed under catalysis by CuCl. Compared with thermal conditions, MW irradiation greatly increases the reaction efficiency. The reactions of various primary N -alkyl/arylamino alcohols, aliphatic/aromatic aldehydes, and alkynes are systematically investigated, affording the desired products in moderate to good yields. Notably, acetylene is also an effective reactant under the current MW-assisted conditions.
- Chen, Ning,Li, Xiang,Xu, Jiaxi
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supporting information
p. 3336 - 3344
(2019/08/28)
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- Selective Reductive Elimination at Alkyl Palladium(IV) by Dissociative Ligand Ionization: Catalytic C(sp3)?H Amination to Azetidines
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A palladium(II)-catalyzed γ-C?H amination of cyclic alkyl amines to deliver highly substituted azetidines is reported. The use of a benziodoxole tosylate oxidant in combination with AgOAc was found to be crucial for controlling a selective reductive elimination pathway to the azetidines. The process is tolerant of a range of functional groups, including structural features derived from chiral α-amino alcohols, and leads to the diastereoselective formation of enantiopure azetidines.
- Nappi, Manuel,He, Chuan,Whitehurst, William G.,Chappell, Ben G. N.,Gaunt, Matthew J.
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supporting information
p. 3178 - 3182
(2018/02/28)
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- AROMATIC COMPOUND
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Provided is a novel aromatic ring compound having a GPR40 agonist activity and a GLP-1 secretagogue action. A compound represented by the formula: wherein each symbol is as described in the DESCRIPTION, or a salt thereof has a GPR40 agonist activity and a GLP-1 secretagogue action, is useful for the prophylaxis or treatment of cancer, obesity, diabetes, hypertension, hyperlipidemia, cardiac failure, diabetic complications, metabolic syndrome, sarcopenia and the like, and affords superior efficacy.
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Paragraph 0937; 0938
(2016/05/19)
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- Synthesis and antibacterial activity of aromatic and heteroaromatic amino alcohols
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Two series of aromatic and heteroaromatic amino alcohols were synthesized from alcohols and aldehydes and evaluated for their antibacterial activities. All the octylated compounds displayed a better activity against the four bacteria tested when evaluated by the agar diffusion method and were selected for the evaluation of minimal inhibitory concentration. The best results were obtained for p-octyloxybenzyl derivatives against Staphylococcus epidermidis (minimal inhibitory concentrations = 32μm).
- de Almeida, Camila G.,Reis, Samira G.,de Almeida, Angelina M.,Diniz, Claudio G.,da Silva, Vania L.,Le Hyaric, Mireille
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p. 876 - 880
(2012/06/18)
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- Facile synthesis of β-amino disulfides, cystines, and their direct incorporation into peptides
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Herein, we report a simple and efficient methodology for the synthesis of β-amino disulfides by regioselective ring opening of sulfamidates with benzyltriethylammonium tetrathiomolybdate [BnNEt3] 2MoS4. Stability and reactivity of different protecting groups under the reaction conditions have been discussed. This methodology has also been extended to serine and threonine derived sulfamidates to furnish cystine and 3,3′-dimethyl cystine derivatives. Georg Thieme Verlag.
- Nasir Baig,Kanimozhi, Catherine K.,Sudhir, V. Sai,Chandrasekaran, Srinivasan
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scheme or table
p. 1227 - 1232
(2009/09/06)
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- 1,5-DIHETEROCYCLE-1H-TRIAZOLE DERIVATIVE
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The present invention relates to a compound represented by Formula (I): wherein Ar1, Ar2, R1 and R2 each represent a substituent, a salt thereof, or a solvate of the compound or the salt, and to a medicine containing the same. According to the present invention, a potent platelet aggregation suppressant which does not inhibit COX-1 and COX-2 is provided.
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(2010/11/27)
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- AMIDOPYRAZOLE DERIVATIVE
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A platelet coagulation inhibitor which inhibits neither COX-1 nor COX-2 is provided. The inhibitor is a compound represented by general formula (I): wherein Ar1 and Ar2 independently represent a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents, or a phenyl group optionally substituted with 1 to 3 substituents; R1 represents a lower acyl group, carboxyl group, a lower alkoxycarbonyl group, a lower alkoxy group, a lower alkyl group optionally substituted with 1 or 2 substituents, a carbamoyl group optionally substituted with 1 or 2 substituents, an oxamoyl group optionally substituted with 1 or 2 substituents, an amino group optionally substituted with 1 or 2 substituents, a 4- to 7-membered alicyclic heterocyclic group optionally substituted with 1 or 2 substituents, a phenyl group optionally substituted with 1 to 3 substituents, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents; and R2 represents hydrogen atom, a halogeno group, or the like.
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Page/Page column 83-84
(2010/11/23)
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- EPR study of dialkyl nitroxides as probes to investigate the exchange of solutes between the ligand shelf of monolayers of protected gold nanoparticles and aqueous solutions
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EPR spectroscopy has been used to study the interaction of para-substituted benzyl hydroxyalkyl nitroxides with the monolayer of water-soluble protected gold cluster made by a short alkyl chain and a triethylene glycol monomethyl ether unit. The inclusion
- Lucarini, Marco,Franchi, Paola,Pedulli, Gian Franco,Pengo, Paolo,Scrimin, Paolo,Pasquato, Lucia
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p. 9326 - 9329
(2007/10/03)
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- AROYL-PIPERAZINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS TACHYKININ ANTAGONISTS
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This invention relates to piperazine derivatives of formula (I), wherein Y is bond or lower alkylene, R1 is aryl which may have substituent(s), R2 is aryl or indolyl, each of which may have substituent(s), R3 is hydrogen or lower alkyl, and R4 is as defined in the description, and its pharmaceutically acceptable salt, to processes for preparation thereof, to pharmaceutical composition comprising the same, and to a use of the same for treating or preventing Tachykinin-mediated diseases in human beings or animals. 1
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- Improved syntheses of fluorinated tertiary butylamines
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Two new and efficient methods using cyclic sulfamidate and nitrone chemistry were developed for the synthesis of the sterically congested 1,1- dimethyl-2-fluoroethylamine (1), 2-fluoro-1-(fluoromethyl)-1-methylethylamine (2) and 2-fluoro-1,1-bis-(fluoromethyl)-ethylamine (3).
- Ok, Dong,Fisher, Michael H.,Wyvratt, Matthew J.,Meinke, Peter T.
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p. 3831 - 3834
(2007/10/03)
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- Bicyclic and tricyclic compounds with β-amino alcohol groups as chiral ligands in the enantioselective reaction of diethylzinc with aldehydes
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Reduction of the enantiomerically pure allyloxy esters 9 or ent-9 with DIBAH afforded the corresponding aldehydes which were treated in situ with chiral or achiral hydroxylamines 8 to give nitrones 10. These underwent a spontaneous intramolecular 1,3-dipolar cycloaddition, affording the bicyclic compounds 11 and 12, respectively. In an analogous manner, a mixture of the tricyclic compounds 14 and 15 was prepared. Treatment of compound 16 with cyclohexene oxide afforded a mixture of diastereomers 17 and 18. Diastereomers 14 and 15 as well as 17 and 18 could be separated by chromatography. X-ray analyses of compounds 11Ff, 17, and 11Af · HCI were performed. The bicyclic and tricyclic compounds were used as chiral ligands in the reaction of diethylzinc with aldehydes 19, in particular with benzaldehyde (19a). Using bicyclic compounds with a tertiary β-hydroxyalkyl substituent at the N atom as ligands, ee's in the range of 78 to 95% were found. Whereas for the best ligands 11Ae and Af the enantioselectivity in the reaction of 4-tolualdehyde was only slightly decreased, with the aliphatic aldehydes 19c and d distinctly lower enantioselectivities were determined. VCH Verlagsgesellschaft mbH, 1997.
- Aurich, Hans Guenter,Biesemeier, Frank,Geiger, Michael,Harms, Klaus
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p. 423 - 434
(2007/10/03)
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- Reductive Cleavage of Aryl Oxazolines to Benzaldehydes and Substituted Toluenes
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Aryl oxazolines have been converted to their corresponding benzaldehydes and toluenes by several routes by passing through the intermediate amino alcohols.The transformations proceeded under mild conditions and were shown to be generally applicable to a variety of substitutions on the aromatic nucleus.
- Meyers, A. I.,Himmelsbach, Richard J.,Reuman, Michael
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p. 4053 - 4058
(2007/10/02)
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- PYRIDYLOXYALKYLENEAMINO-PHENOXY-PROPANOL-2-COMPOUNDS
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Compounds of the formula STR1 WHEREIN Ar 1 and Ar 2 denote an optionally substituted aromatic hydrocarbon radical or a monocyclic, monoazacyclic or diazacyclic radical of aromatic character and Alk represents lower alkylene, or salts thereof, exhibit β-receptor-blocking, blood pressure-lowering and vasodilatory effects and are useful for example in the treatment of arrythmias and angina pectoris, and as blood pressure-lowering agents.
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