- Synthesis and evaluation of novel monosubstituted sulfonylurea derivatives as antituberculosis agents
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A series of novel monosubstituted sulfonylurea derivatives 10a-y were synthesized and characterized by 1H NMR, 13C NMR and HRMS. These compounds were evaluated against Mycobacterium tuberculosis H37Rv in vitro. The results showed compounds 10f, 10k and 10s exhibited moderate antituberculosis activities with MIC values in the range of 20-100 mg/L. Compounds 10b and 10o displayed good antituberculosis activities (MIC 10 mg/L), which were comparable with that of the sulfometuron methyl. Both of the two compounds showed little cytotoxicities, with an IC50 against THP-1 cells greater than 100 mg/L.
- Pan, Li,Jiang, Ying,Liu, Zhen,Liu, Xing-Hai,Liu, Zhuo,Wang, Gang,Li, Zheng-Ming,Wang, Di
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scheme or table
p. 18 - 26
(2012/07/01)
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- Synthesis and properties of β-ethoxyvinyl polyfluoroalkyl ketones
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A number of β-ethoxyvinyl polyfluoroalkyl ketones were synthesized by acylation of ethyl vinyl ether with acid chlorides containing polyfluoroalkyl groups of different composition and structure. Some typical nucleophilic reactions of the title compounds with amines were carried out. Two new fluoro-containing pyrimidinoles were synthesized by the reaction of β- ethoxyvinyl polyfluoroalkyl ketones with urea.
- Gorbunova, Marine G.,Gerus, Igor I.,Kukhar, Valery P.
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p. 738 - 742
(2007/10/03)
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- Multiple pathways in cyclodextrin-catalyzed hydrolysis of perfluoroalkylamides
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The hydrolysis of p-nitroanilide of perfluoroalkanoic acids, CF3(CF2)nCO-, with n = 1, 2, 3, 5, 6, and 7, 1a-f, was studied in the presence of β-cyclodextrin (CD). All reactions were catalyzed by CD through the formation of a 1:1 and 1:2 inclusion complexes. The association equilibrium constants for the 1:1 complexes were dependent on the number of carbons of the fluoroalkyl chain, whereas those of the 1:2 complexes were almost independent. These results indicate that, in the former case, the perfluoroalkyl chain is included, while in the latter, the CD unit encloses the aryl ring. For compounds 1a,b both complexes were more reactive than the substrate itself. The ratio of the reaction of complexed to uncomplexed substrate had its highest value for 1a in the case of the 1:1 complex, and for 1b, the 1:2 complex. This is attributed to the geometry of the complexes. Although compounds 1c-e reacted at the same rates in the free or 1:1 complexed form, CD accelerated the reactions because of an increase of the pKa of the substrate, which results in a higher concentration of the neutral reactive substrate at the same pH. Compound 1f formed aggregates even at 10-6 M concentration, and CD-induced deaggregation resulted in catalysis of the reaction.
- Granados, Alejandro,De Rossi, Rita H.
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p. 3690 - 3696
(2007/10/02)
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- REGIOSPECIFIC PREPARATION OF α,α-DIHALOFLUOROMETHYL PERFLUOROALKYL KETONES.
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Acylation of F-phosphoranium salts with F-acyl chlorides gives the corresponding Z-perfluoro betaine in high yield.Subsequent chlorination or bromination regiospecifically yields the α,α-dihalofluoromethyl perfluoroalkyl ketones.
- Jeong, In Howa,Burton, Donald J.,Cox, Daryl G.
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p. 3709 - 3712
(2007/10/02)
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- The Decomposition of t-Butyl Heptafluoroperoxybutyrate in Aromatic and Aliphatic Solvents
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Kinetical studies and products analyses of the thermal decomposition of t-butyl heptafluoroperoxybutyrate (TBH) in benzene, octane, nitrobenzene, pyridine, and methoxybenzene have been carried out.In benzene and octane, the decoposition appears to be entirely a radical process.In nitrobenzene and pyridine, the reactions are found to give ionic decomposition proudcts exclusively.On the other hand, the decomposition of TBH in methoxybenzene is characteristic of mixed ionic and radical cleavages.
- Sawada, Hideo,Hagii, Hidehiko,Aoshima, Kazuyoshi,Yoshida, Masato,Kobayashi, Michio
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p. 3448 - 3452
(2007/10/02)
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- Thermal Decomposition of Some Perfluoro- and Polyfluorodiacyl Peroxides
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Seven polyfluoroacyl peroxides were synthesized, some of them by a new procedure involving the direct interaction of an acyl fluoride with hydrogen peroxide.In the temperature range of 20-40 deg C, all these peroxides undergo first-order decomposition in dilute 1,1,2-trichloro-1,2,2-trifluoroethane (Freon-113) solutions (F-RF.Differing from other perfluoro or polyfluoro radicals, the perfluoro-α-isopropoxyethyl radicals (10) undergo substantial β scission to form perfluoroisopropyl radicals (11) during their lifetime.The ΔHexc. values for the perfluoroacyl peroxides are about 24 kcal mol-1, or about 5 kcal lower than that of the nonfluorinated diacyl peroxides (ca. 29 kcal mol-1).Apparently, the higher relative rates for 3 and 7 are caused by different factors.The latter peroxide (7) decomposes with a more favorable ΔSexc. term, whereas the former (3) decomposes with lower values of both ΔHexc. and ΔSexc..Thus, weakening of the peroxide bond by H bonding of the peroxide oxygen atom with the acidic ω-hydrogen atom seems to be implicated in the decomposition of 3.With a half-life of 81 min at 20 deg C, 3 may become a useful low-temperature initiator for free-radical reactions and polymerization.
- Chengxue, Zhao,Renmo, Zhou,Heqi, Pan,Xiangshan, Jin,Yangling, Qu,et al.
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p. 2009 - 2013
(2007/10/02)
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- PERFLUOROACYLFLUOROSULFONYLFLUOROACETIC ESTERS
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In the presence of triethylamine the esters of fluorosulfonylfluoroacetic acid are acylated by the chlorides and anhydrides of perfluorinated carboxylic acids to form previously unknown esters of perfluoroacylfluorosulfonylfluoroacetic acids.A characteristic feature of the latter is the presence of carbonyl, alkoxycarbonyl, and fluorosulfonyl groups at one carbon atom.
- Eleev, A. F.,Ermolov, A. F.,Kutepov, A. P.,Sokol'skii, G. A.,Chekholin, V. K.
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p. 1467 - 1471
(2007/10/02)
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- SYNTHESE ET CARACTERISTIQUES SPECTRALES DE F-ALKYL-2-DIHYDRO-3,4 OXO-4 QUINAZOLINES
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In this paper we report the preparation of a series of 4(3H) quinazolinones substituted in the 2 position by a linear perfluoroalkyl-chain with RF as Cn F2n+1 (n=1,3,5,7).These compounds are obtained in two steps, action of F-acid chlorides on 2-aminobenzonitrile which affords the corresponding F-amides followed by cyclization of this intermediate with alkaline hydrogen peroxide.We isolated a reaction intermediate in the cyclization of N-(2-cyanophenyl)F-octanamide.All compounds were identified by the usual spectroscopic methods (IR, NMR 1H, 19F, mass spectrometry).
- Greiner, Jacques,Pastor, Raphael,Cambon, Aime
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p. 185 - 196
(2007/10/02)
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