- Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions
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Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.
- Li, Jiaming,Li, Jian,Ji, Xiaoliang,He, Runfa,Liu, Yang,Chen, Zebin,Huang, Yubing,Liu, Qiang,Li, Yibiao
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supporting information
p. 7412 - 7417
(2021/10/01)
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- Improved flavodoxin inhibitors with potential therapeutic effects against Helicobacter pylori infection
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Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.
- Galano, Juan J.,Alías, Miriam,Pérez, Reyes,Velázquez-Campoy, Adrian,Hoffman, Paul S.,Sancho, Javier
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p. 6248 - 6258
(2013/09/02)
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- Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues
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In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 μM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl]caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 μM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.
- Mostert, Samantha,Mentz, Wayne,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.
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p. 7040 - 7050
(2013/01/15)
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- Synthesis of raphanuside, an unusual oxathiane-fused thioglucoside isolated from the seeds of Raphanus sativus L.
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Raphanuside (1), an unusual oxathiane-fused thioglycoside isolated from the seeds of Raphanus sativus L., was synthesized via 10 steps and in 11% overall yield.{A figure is presented}.
- Yang, Fei,Lian, Gaoyan,Yu, Biao
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experimental part
p. 309 - 314
(2010/03/26)
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- SYNTHESIS OF 1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-2,6-EPITHIO-3-BENZAZOCINE
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In anticipation of diminishing narcotism of 1,2,3,4,5,6-hexahydro-8-hydroxy-2,6-methano-3-benzazocine opioids, the corresponding 2,6-epithio-3-benzazocines (2) have been synthesized by intramolecular cyclization of 1-(2-aminoethyl)-3,4-dihydro-1H-2-benzothiopyrans (9) with tert-butyl hypochlorite, and subsequent treatment of the 5-membered cyclic aminosulfonium salts (17) with NaOH.
- Hori, Mikio,Ozeki, Hiroyuki,Iwamura, Tatsunori,Shimizu, Hiroshi,Kataoka, Tadashi,Iwata, Noriyuki
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- PHENOL ETHERS
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The invention provides phenol ethers of the formula: STR1 wherein R is branched C 3-4 alkyl, C 3-4 cycloalkyl, branched cyano(C 3-4 alkyl), phenyl(C 2-3 alkyl), halophenyl(C 2-3 alkyl), (C 1-4 alkoxy)phenyl(C 2-4 alkyl), or (C 1-4 acyl) amino(C 1-4 alkyl),alk is C 1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is--O--,--S--or--SO 2--; andR 1 is--C 1-4 alkyl-or--C 1-4 alkoxy-, in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as β-adrenergic blocking agents. Intermediates are also provided.
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