- Weak, bidentate chelating group assisted cross-coupling of C(sp3)-H bonds in aliphatic acid derivatives with aryltrifluoroborates
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A protocol of Pd(ii)-catalyzed, weak bidentate directing group assisted β-C(sp3)-H activation/cross-coupling with organoboron reagents has been achieved, affording arylation of aliphatic acid derivatives that contain α-hydrogen atoms in moderate to good yields. The potential of this method for an asymmetric β-C(sp3)-H arylation via desymmetrization was also presented.
- Cai, Zhihua,Li, Shangda,Gao, Yuzhen,Fu, Lei,Li, Gang
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supporting information
p. 12766 - 12769
(2018/11/23)
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- Substituents effects on activity of kynureninase from Homo sapiens and Pseudomonas fluorescens
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A series of substituted kynurenines (3-bromo-dl, 3-chloro-dl, 3-fluoro-dl, 3-methyl-dl, 5-bromo-l, 5-chloro-l, 3,5-dibromo-l and 5-bromo-3-chloro-dl) have been synthesized and tested for their substrate activity with human and Pseudomonas fluorescens kynureninase. All of the substituted kynurenines examined have substrate activity with both human as well as P. fluorescens kynureninase. For the human enzyme, 3- and 5-substituted kynurenines have k cat and kcat/Km values higher than l-kynurenine, but less than that of the physiological substrate, 3-hydroxykynurenine. However, 3,5-dibromo- and 5-bromo-3-chlorokynurenine have kcat and kcat/Km values close to that of 3-hydroxykynurenine with human kynureninase. The effects of the 3-halo substituents on the reactivity with human kynureninase may be due to electronic effects and/or halogen bonding. In contrast, for the bacterial enzyme, 3-methyl, 3-halo and 3,5-dihalokynurenines are much poorer substrates, while 3-fluoro, 5-bromo, and 5-chlorokynurenine have kcat and kcat/K m values comparable to that of its physiological substrate, l-kynurenine. Thus, 5-bromo and 5-chloro-l-kynurenine are good substrates for both human as well as bacterial enzyme, indicating that both enzymes have space for substituents in the active site near C-5. The increased activity of the 5-halokynurenines may be due to van der Waals contacts or hydrophobic effects. These results may be useful in the design of potent and/or selective inhibitors of human and bacterial kynureninase.
- Maitrani, Chandan,Phillips, Robert S.
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p. 4670 - 4677
(2013/07/26)
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- Synthesis of insecticidal fluorinated anthranilic diamides
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A series of highly active fluorinated anthranilic diamide insecticides have been prepared and their biological activity assessed on two aphid species in the search for systemically active compounds that control Hemiptera. In addition, we have demonstrated a new synthesis of N-aryl 3-fluoropyrazoles.
- Clark, David A.,Lahm, George P.,Smith, Ben K.,Barry, James D.,Clagg, Don G.
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p. 3163 - 3170
(2008/09/20)
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- Condensed pyrazole derivatives, process for producing the same and use thereof
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Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): or salts thereof.
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- Antimicrobial activity of fluorinated 1,2-benzisothiazol-3(2H)-ones and 2,2'-dithiobis(benzamides)
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Fluoro and trifluoromethyl derivatives of 1,2-benzisothiazol-3(2H)-ones and the 2,2'-dithiobis(benzamides) have been prepared and their antifungal and antibacterial activity evaluated. Several compounds were found highly active against fungi and Gram-positive microorganisms and a few derivatives displayed some activity against Gram-negative strains. Structure-activity relationships are proposed.
- Carmellino,Pagani,Pregnolato,Terreni,Pastoni
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p. 743 - 751
(2007/10/02)
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- Process for the preparation of 3- and/or 5-substituted anthranilic acids
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Anthranilic acids substituted in the 3- and/or 5-position are valuable intermediates for the production of agricultural chemicals. These substituted anthranilic acids can be obtained in good yield without undesirable isomeric byproducts by the oxidative r
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- Synthetic Entries to 6-Fluoro-7-substituted Indole Derivatives
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Three practical synthetic entries of functionalized 6-fluoro-7-substituted indole derivatives were developed in connection with the preparation of 7-fluoro-8-substituted-1,3,4,9-tetrahydropyranoindole-1-acetic acid derivatives 11.The first route, w
- McKittrick, Brian,Failli, Amedeo,Steffan, Robert J.,Soll, Richard M.,Hughes, Philip,et al.
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p. 2151 - 2163
(2007/10/02)
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- Certain 1,3-dihydro-1-[heterocyclic)imino]-furo-[3,4-b]quinoline 9-ol compounds having analgesic and anti-inflammatory activity
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A 4-hydroxy-3-quinoline-carboxamides of the formula STR1 wherein X is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CH3, --OCF3/su
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- AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF 3-FLUOROANTHRANILIC ACID
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3-Ffluoroanthranilic acid is derived in four steps from 3-nitrophthalic acid in 53percent overall yield.
- Milner, David J.
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p. 485 - 490
(2007/10/02)
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- 4-Hydroxy-3-quinoline-carboxylic acid derivatives
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Novel 4-hydroxy-3-quinoline-carboxamides of the formula STR1 wherein X is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF3, --OCF3
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- Method for the preparation of fluoroaniline
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A process for the preparation of fluoroaniline compounds comprises the steps of (A) reacting an ammonium fluorophthalamate or a fluorophthalamic acid of the formula STR1 where n is 1 or 2 with an alkali or an alkali earth metal hypochlorite to form the corresponding fluoroanthranilic acid; and (B) decarboxylating the fluoroanthranilic acid by reaction with a mineral acid to form the corresponding fluoroaniline of the formula STR2 where n is as previously defined.
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