- Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
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A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
- Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
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supporting information
p. 6105 - 6109
(2021/08/18)
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- Preparation method of 3-bromopropionate compound
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The invention relates to the field of organic synthesis, and discloses a preparation method of a 3-bromopropionate compound. The method comprises the following steps: reacting acetyl bromide used as araw material with an alcohol solvent to generate hydrogen bromide in situ, and carrying out a 1,4-addition reaction on the hydrogen bromide and an acrylate compound to obtain the 3-bromopropionate compound. According to the invention, the preparation method disclosed by the invention belongs to a one-pot method in chemistry and has few steps; by-products of acetate and alcohol solvents can be rectified and recycled, so that less three wastes are generated; and more importantly, the boiling points of the product acetate and the product 3-bromopropionate compound generated by the reaction haveobvious difference, so that distillation or rectification separation is facilitated after the reaction is finished.
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Paragraph 0027
(2020/06/30)
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- Synthesis of N-Substituted phosphoramidic acid esters as “reverse” fosmidomycin analogues
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An efficient synthetic pathway to a series of novel “reverse” fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial “pro-drugs”.
- Adeyemi, Christiana M.,Hoppe, Heinrich C.,Isaacs, Michelle,Klein, Rosalyn,Lobb, Kevin A.,Kaye, Perry T.
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p. 2371 - 2378
(2019/03/23)
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- Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2
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It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.
- Mostyn, Shannon N.,Carland, Jane E.,Shimmon, Susan,Ryan, Renae M.,Rawling, Tristan,Vandenberg, Robert J.
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p. 1949 - 1959
(2017/09/26)
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- Antimicrobial poly(2-methyloxazoline)s with bioswitchable activity through satellite group modification
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Biocides are widely used for preventing the spread of microbial infections and fouling of materials. Since their use can build up microbial resistance and cause unpredictable long-term environmental problems, new biocidal agents are required. In this study, we demonstrate a concept in which an antimicrobial polymer is deactivated by the cleavage of a single group. Following the satellite group approach, a biocidal quaternary ammonium group was linked through a poly(2-methyloxazoline) to an ester satellite group. The polymer with an octyl-3-propionoate satellite group shows very good antimicrobial activity against Gram-positive bacterial strains. The biocidal polymer was also found to have low hemotoxicity, resulting in a high HC50/MIC value of 120 for S. aureus. Cleaving the ester satellite group resulted in a 30-fold decrease in antimicrobial activity, proving the concept valid. The satellite group could also be cleaved by lipase showing that the antimicrobial activity of the new biocidal polymers is indeed bioswitchable. Biocides are widely used for preventing the spread of microbial infections and the fouling of materials. Since their application can build up microbial resistance and cause unpredictable long-term environmental problems, new biocidal agents are required. In a novel approach an antimicrobial polymer is deactivated by hydrolysis of an ester group through the action of a lipase. The crucial feature is the mutual interaction of the two endgroups of the polymer.
- Krumm, Christian,Harmuth, Simon,Hijazi, Montasser,Neugebauer, Britta,Kampmann, Anne-Larissa,Geltenpoth, Helma,Sickmann, Albert,Tiller, Joerg C.
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supporting information
p. 3830 - 3834
(2014/05/06)
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- Spirocyclic Azaindole Derivatives
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The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.
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Page/Page column 10
(2009/07/03)
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- A FACILE METHOD FOR THE CONVERSION OF PRIMARY ALKYL CHLORIDES TO THE CORRESPONDING BROMIDES
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Treatment of several representative primary alkyl chlorides with one equivalent of sodium bromide in 2:1 (v/v) N,N-dimethylformamide : dibromoethane at 100 deg C for several hours resulted in their quantitative conversion to the corresponding bromides.
- Babler, James H.,Spina, Kenneth P.
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p. 1313 - 1320
(2007/10/02)
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