- Synthetic process of 2,3-dichlorobenzaldehyde
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The invention discloses a synthetic process of 2,3-dichlorobenzaldehyde. The synthetic process comprises the steps that 2,3-dichlorotoluene is used as a raw material, bromine is used as an auxiliary material, azodiisobutyronitrile is used as a catalyst, the bromine utilization rate is improved through hydrogen peroxide, the generated 2,3-dichlorobenzyl bromide is hydrolyzed into 2,3-dichlorobenzaldehyde in 30 wt% of sodium carbonate water solution, the 2,3-dichlorobenzaldehyde is generated by using hydrogen bromide to catalyze hydrogen peroxide oxidization, the total yield is 70% or above, and the product purity is 99.25% or above. The raw material conversion rate and selectivity of the process are high. In addition, the by-product production rate is reduced, the bromine utilization rate is improved, the bromine usage amount is decreased, and the synthetic process is greener and environmentally friendly compared with a traditional metal-catalyzed oxidation technology.
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- Selective Pinacol-Coupling Reaction using a Continuous Flow System
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The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.
- Sotto, Nicolas,Cazorla, Clément,Villette, Carole,Billamboz, Muriel,Len, Christophe
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p. 11065 - 11071
(2016/11/28)
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- O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1
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Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.
- Malachowski, William P.,Winters, Maria,DuHadaway, James B.,Lewis-Ballester, Ariel,Badir, Shorouk,Wai, Jenny,Rahman, Maisha,Sheikh, Eesha,LaLonde, Judith M.,Yeh, Syun-Ru,Prendergast, George C.,Muller, Alexander J.
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supporting information
p. 564 - 576
(2016/01/09)
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- Simple and expeditious pinacol coupling of non usual α,β-unsaturated carbonyl compounds in water
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Using zinc (0) in a 5% v AcOH aqueous solution allowed the efficient pinacol coupling of aliphatic or aromatic unusual, α,β-unsaturated carbonyl compounds such as citral A in good to excellent yields (56-99%). It can also be successfully applied to acetophenone.
- Billamboz, Muriel,Sotto, Nicolas,Chevrin-Villette, Carole,Len, Christophe
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p. 46026 - 46030
(2015/06/08)
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- First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies
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For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.
- Billamboz, Muriel,Len, Christophe
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p. 1664 - 1675
(2015/06/02)
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- Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water
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Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.
- Sotto, Nicolas,Billamboz, Muriel,Chevrin-Villette, Carole,Len, Christophe
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p. 6375 - 6380
(2015/06/30)
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- Pyrazolopyrimidine derivatives as PI3 kinase inhibitors
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PI3Kβ selective compounds having the structure
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- Metal-free, visible-light photoredox catalysis: Transformation of arylmethyl bromides to alcohols and aldehydes
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A mild, simple, and controllable metal-free photocatalytic system for the transformation of arylmethyl bromides to corresponding alcohols and aldehydes in high yields with visible-light irradiation has been achieved. Eosin Y was found to be an efficient promoter for this oxidative dehalogenation reaction under photo irradiation conditions.
- Li, Jian,Wang, Hongni,Liu, Li,Sun, Jiangtao
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p. 49974 - 49978
(2014/12/10)
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- Electrophilicity and nucleophilicity of commonly used aldehydes
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The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
- Pratihar, Sanjay
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p. 5781 - 5788
(2014/07/22)
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- PYRAZOLOPYRIMIDINE DERIVATIVES AS PI3 KINASE INHIBITORS
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The present invention relates to compounds of formula (I) in which R1, R2, R3 and n have the meaning given in the specification and also relates to the use of these pyrazolopyrimidine derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3'OΗ kinase family (hereinafter PI3 kinases), wherein the compounds of formula (I) are described as selective inhibitors of PI3K[beta] activity.
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- Novel piperidinecarboxamide derivatives, method for preparing same and pharmaceutical compositions containing same
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The invention relates to compounds of formula: as well as their salts with inorganic or organic acids, their solvates and/or their hydrates, which exhibit a very high affinity both for the human NK2 receptors for neurokinin A and for the human NK3 receptors for neurokinin B and are antagonists of the said receptors. The invention also relates to their method of preparation, the pharmaceutical compositions containing them and their use for the preparation of medicaments.
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- A simple reduction of methyl aromatic esters to alcohols using sodium borohydride-methanol system
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Several aromatic esters were reduced to the corresponding alcohol by using sodium borohydride-methanol system. The reduction was completed within 2.0-4.0h after refluxing in THF. The alcohol products were isolated after aqueous workup in good yields (88-97%).
- Boechat, Núbia,Santos Da Costa, Jorge Carlos,De Souza Mendon?a, Jorge,Mello De Oliveira, Pedro Santos,Nora De Souza, Marcus Vinícius
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p. 6021 - 6022
(2007/10/03)
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- Sodium channel drugs and uses
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The compounds of this invention comprise 2-10 ligands covalently connected, each of the ligands being capable of binding to a ligand binding site in a Na+channel, thereby modulating the biological activities thereof.
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- Optically active phenyl pyrimidine derivatives as analgesic agent
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PCT No. PCT/EP96/03856 Sec. 371 Date Feb. 26, 1998 Sec. 102(e) Date Feb. 26, 1998 PCT Filed Sep. 3, 1996 PCT Pub. No. WO97/09317 PCT Pub. Date Mar. 13, 1997A pyrimidine of formula (I) and its pharmaceutically acceptable acid addition salts are useful as a
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- Antihypertensive Activity of 6-Arylpyridopyrimidin-7-amine Derivatives
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A series of 51 6-arylpyridopyrimidin-7-amine derivatives was prepared and evaluated for antihypertensive activity in the conscious spontaneously hypertensive rat.A number of these compounds, notably 6-(2,6-dichlorophenyl)-2-methylpyridopyrimidin-7-amine (36), lowered blood pressure in these rats in a gradual and sustained manner to normotensive levels at oral doses of 10-50 mg/kg.Normalized blood pressure levels could then be maintained by single daily oral doses.The effect of structural variation in the 6-aryl group and in the 2 and 4 positions of the pyridopyrimidine ring on activity is reported and discussed.
- Bennett, Lawrence R.,Blankley, C. John,Fleming, Robert W.,Smith, Ronald D.,Tessman, Deirdre K.
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p. 382 - 389
(2007/10/02)
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- Anti-inflammatory 1-(substituted benzyl)-2-imidazolidinones
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Certain 1-(substituted benzyl)-2-imidazolidinones of the formula: SPC1 Wherein Ar is 4-chlorophenyl, 3-fluorophenyl, 2,3-dichlorophenyl, and 1-naphthyl possess pharmacological activity as anti-inflammatory agents.
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