133531-43-8Relevant articles and documents
Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides
Barder, Timothy E.,Buchwald, Stephen L.
, p. 2649 - 2652 (2004)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl- and heteroaryl chlorides with potassium aryl- and heteroaryltrifluoroborates have been accomplished with the supporting ligand S-Phos in good to excellent yield. Hindered biaryls and substrates containing a variety of functional groups can be prepared. Suzuki-Miyaura couplings of a 3-pyridyl boron-based nucleophile with aryl- and heteroaryl chlorides proceed in good to very good yield.
Selective Targeting of the TPX2 Site of Importin-α Using Fragment-Based Ligand Design
Holvey, Rhian S.,Valkov, Eugene,Neal, David,Stewart, Murray,Abell, Chris
supporting information, p. 1232 - 1239 (2015/07/07)
Protein-protein interactions are difficult therapeutic targets, and inhibiting pathologically relevant interactions without disrupting other essential ones presents an additional challenge. Herein we report how this might be achieved for the potential ant
Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
Luo, Bao-Tian,Liu, Huan,Lin, Zhi-Jie,Jiang, Jingxing,Shen, Dong-Sheng,Liu, Rui-Zhi,Ke, Zhuofeng,Liu, Feng-Shou
, p. 4881 - 4894 (2015/11/09)
In the present work, a series of α-hydroxyimine palladium complexes with bulky substituents (i.e., {[Ar-N=C(R)-C(R)2-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.
Ligand-less palladium-catalyzed direct 5-arylation of thiophenes at low catalyst loadings
Roger, Julien,Pozgan, Franc,Doucet, Henri
experimental part, p. 425 - 432 (2010/04/22)
Ligand-less Pd(OAc)2 provides a very efficient catalyst for the direct 5-arylation of thiophene derivatives. With this catalyst, a low palladium concentration (0.1-0.001 mol%) should be employed in order to obtain high yields of coupling products. At higher concentrations a fast formation of inactive "Pd black" generally occurs. Substrates/catalysts ratios up to 100000 can be employed with the most reactive aryl bromides. A very wide variety of functional groups is tolerated on both coupling partners. The major waste of this reaction is HBr associated with KOAc. Therefore this procedure is more economically and environmentally attractive than the traditional cross-coupling procedures employing organometallic derivatives.
Synthesis and antibacterial activity of novel C12 vinyl ketolides
Burger, Matthew T.,Lin, Xiaodong,Chu, Daniel T.,Hiebert, Christy,Rico, Alice C.,Seid, Mehran,Carroll, Georgia L.,Barker, Lynn,Huh, Kay,Langhorne, Mike,Shawar, Ribhi,Kidney, Jolene,Young, Kelly,Anderson, Scott,Desai, Manoj C.,Plattner, Jacob J.
, p. 1730 - 1743 (2007/10/03)
A novel series of C12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C12 modification involves replacing the natural C 12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C12 vinyl macrolide core, a series of C12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles of C12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.
SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
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Page/Page column 95, (2010/02/12)
Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.
5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6
Denton, Travis T.,Zhang, Xiaodong,Cashman, John R.
, p. 224 - 239 (2007/10/03)
A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2B6, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.
PIPERIDINES USEFUL FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
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Page 39; 42, (2008/06/13)
The invention relates to compounds which are substituted chiral or achiral derivatives of 3- or 4- aminopiperidine of the general formula (I). The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of general formula I and especially their use as inhibitors of β-secretases.
SUBSTITUTED 3- AND 4- AMINOMETHYLPIPERIDINES FOR USE AS BETA-SECRETASE IN THE TREATMENT OF ALZHEIMER’S DISEASE
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Page/Page column 48, (2008/06/13)
The invention relates to novel compounds, which are substituted chiral or achiral derivatives of 3- or 4- aminomethylpiperidine of the general formula (I). The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of general formula (I) and especially their use as inhibitors of beta-secretases for the treatment of Alzheimer’s disease.
Azabicyclic-substituted-heteroaryl compounds for the treatment of disease
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, (2008/06/13)
The invention provides compounds of Formula I: Azabicyclo-N(R1)—C(═X)—W??Formula I These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful
