- Spectroscopic characterization of 1:1 complexes of some carbon acids activated by two sulfonyl groups with 1,5,7-triazabicyclo[4.4.0]dec-5-ene in acetonitrile
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The series of six carbon acids activated by two sulfonyl groups have been synthesized and the products of their deprotonation in acetonitrile solution by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were defined by electrospray ionization mass spectrometry method. The deprotonation of carbon acids and derivative fragmentary carbanions at various cone voltage are compared. Substituent effect on the fragmentation of molecular anions and heats of formation are reported. The fragmentation pathways of the carbanions of studied carbon acids are proposed and the differences in fragmentation of these ions are discussed. The calculated heats of formation of molecular and fragmentary carbanions reveal good Hammett plots against σ values.
- Binkowska, Iwona
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- Thiocarbonyl Surrogate via Combination of Potassium Sulfide and Chloroform for Dithiocarbamate Construction
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An efficient and practical thiocarbonyl surrogate via combination of potassium sulfide and chloroform was established. A variety of dithiocarbamates were afforded along with four new chemical bond formations in a one-pot reaction in which the thiocarbonyl
- Tan, Wei,J?nsch, Niklas,?hlmann, Tina,Meyer-Almes, Franz-Josef,Jiang, Xuefeng
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supporting information
p. 7484 - 7488
(2019/10/08)
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- Narciclasine derivative, and preparation and application thereof in preparation of antitumor drugs
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The invention provides a narciclasine derivative represented by the following structural formula I, wherein R1 is alkyl, cycloalkyl, benzyl or substituted benzyl, R2 is alkyl, cycloalkyl, benzyl or substituted benzyl, and n is an integer from 1 to 10. The narciclasine derivative is subjected to a tumor cell toxicity killing effect test, and results prove that the narciclasine derivative has strong toxicity killing effects on lung gland tumor cells, intestinal tumor cells, breast tumor cells, liver tumor cells, prostate tumor cells, melanoma tumor cells, endometrial tumor cells and neuroglia tumor cells, so the narciclasine derivative can be used for preparation of antitumor drugs. The invention provides a preparation method of the narciclasine derivative. The narciclasine derivative has a novel side-chain structure, shows excellent inhibitory activity on a variety of tumor cell strains, has drug efficacy better than that of narciclasine, allows toxic and side effects of the compound to be improved, provides new drugs for treatment of malignant tumors, and is of great clinical application value.
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Paragraph 0063; 0076; 0077; 0078
(2017/04/28)
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- Novel glucose-based brain-targeting prodrug with locking function
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The invention discloses a novel glucose-based TDS modified brain-targeting prodrug with a locking function. The prodrug is of a structure shown in a general formula (I) (described in the specification) or pharmaceutically acceptable salt of hydrate of the structure, wherein X is -NH-(CH2)m-O-, -NH-(CH2)m-NH-, -C(O)-(CH2)m-NH-, -C(O)-(CH2)m-O-, -O-(CH2)m-O-, -O-(CH2)m-NH-; Y is -C(O)-(CH2)n-C(O)-; m represents 2-6, n represents 1-4; Drug is a drug acting on a central nervous system. A series of prodrugs provided by the invention, on the basis of glucose brain targeting, are added with a TDS part, so that the prodrugs have the locking function, brain targeting and center concentration of the drug can be improved, the curative effect of the drug is enhanced, and distribution of the drug in peripheral organs is reduced while toxic and side effects of the drug are reduced.
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Paragraph 0027
(2016/10/10)
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- Design, synthesis and biological evaluation of brain-targeted thiamine disulfide prodrugs of ampakine compound LCX001
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: Ampakine compounds have been shown to reverse opiate-induced respiratory depression by activation of amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) glutamate receptors. However, their pharmacological exploitations are hindered by low blood-brain barrier (BBB) permeability and limited brain distribution. Here, we explored whether thiamine disulfide prodrugs with the ability of "lock-in" can be used to solve these problems. A series of thiamine disulfide prodrugs 7a-7f of ampakine compound LCX001 was synthesized and evaluated. The trials in vitro showed that prodrugs 7e, 7d, 7f possessed a certain stability in plasma and quickly decomposed in brain homogenate by the disulfide reductase. In vivo, prodrug 7e decreased the peripheral distribution of LCX001 and significantly increased brain distribution of LCX001 after i.v. administration. This compound showed 2.23- and 3.29-fold greater increases in the AUC0-t and MRT0-t of LCX001 in brain, respectively, than did LCX001 itself. A preliminary pharmacodynamic study indicated that the required molar dose of prodrug 7e was only one eighth that of LCX001 required to achieve the same effect in mice. These findings provide an important reference to evaluate the clinical outlook of ampakine compounds.
- Xiao, Dian,Meng, Fan-Hua,Dai, Wei,Yong, Zheng,Liu, Jin-Qiu,Zhou, Xin-Bo,Li, Song
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- Deep eutectic mixture catalysed the synthesis of disulfides using Bunte salts as thiol surrogates
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Bunte salts, easily prepared from odourless sodium thiosulfates and various alkyl and aryl halides, acted as thiol surrogates for preparation of disulfides in the presence of hydrogen peroxide and a Bronsted-acidic deep eutectic mixture. The reaction proceeded smoothly to give the corresponding disulfide products in moderate to good yields, leaving odourless sodium bisulfite and water as the by-products. Moreover, this catalytic system could be readily recovered and reused several times without significant loss in activity.
- Zhou, Yongsheng
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p. 332 - 335
(2015/08/18)
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- Transition-metal-free persulfuration to construct unsymmetrical disulfides and mechanistic study of the sulfur redox process
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A sulfur redox process has been developed between sulfinate and thiosulfate, which efficiently affords diverse unsymmetrical disulfides and provides a new method to modify pharmaceuticals and natural products without requiring an extra oxidant or reductant. Gram-scale investigation further demonstrates the practicality and application potential of this process. Isolated key intermediates and a series of control experiments afford an unusual process, which reveals the mechanism of comproportionation and the transition-metal-free sulfur redox process.
- Xiao, Xiao,Feng, Minghao,Jiang, Xuefeng
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supporting information
p. 4208 - 4211
(2015/03/30)
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- The reaction of grignard reagents with bunte salts: A thiol-free synthesis of sulfides
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S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts) react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-
- Reeves, Jonathan T.,Camara, Kaddy,Han, Zhengxu S.,Xu, Yibo,Lee, Heewon,Busacca, Carl A.,Senanayake, Chris H.
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supporting information
p. 1196 - 1199
(2014/03/21)
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- Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen
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Glucosyl derivates exhibited favorable distribution to the brain. However, bidirectional transport of glucose transporter 1 might decrease concentrations of the prodrugs in brain before the release of parent drugs. To overcome this defect, glucosyl thiamine disulfide prodrugs 1a-1c incorporating naproxen were designed and synthesized. Furthermore, prodrug 2 and 3 were also prepared as control. The favorable physicochemical properties of these prodrugs were verified by stability and metabolism studies. Results from the in vivo distribution study indicated that 1a-1c, and 1b in particular, significantly increased the level of naproxen in brain when compared to 2 and 3. The study suggested glucosyl thiamine disulfide was a promising carrier to enhance the brain bioavailability of central nervous system active drugs.
- Fan, Wei,Wu, Yong,Li, Xian-Kun,Yao, Nian,Li, Xun,Yu, Yong-Guo,Hai, Li
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experimental part
p. 3651 - 3661
(2011/11/06)
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- Quaternary bis-ammonium salt precursors and their uses as prodrugs having an antiparasitic activity
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The invention concerns drug precursors with antimalarial effect, characterised in that it consists in quaternary bis-ammonium salts of general formula (I) wherein A and A′, identical or different, are respectively either a group A1 and A′1 of formula (1)
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Page/Page column 9
(2010/02/14)
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- Antimicrobial activity of organic thiosulfates (Bunte salts)
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A number of organic thiosulfates (Bunte salts) were prepared from appropriate primary bromides or iodides. In the case of substrates with long aliphatic chains, an addition of benzyltrimethylammonium chloride as phase transfer catalyst was very successful
- Stefanska,Starosciak,Orzeszko,Kazimierczuk
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p. 190 - 192
(2007/10/03)
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- Preparation of disulfides by reduction of sodium alkyl thiosulfates with metallic samarium and catalytic amount of iodine
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Sm/I2 reduces sodium alkyl thiosulfates to the corresponding disulfides in good to excellent yields in THF at room temperature.
- Huang, You,Zhang, Yongmin,Wang, Yulu
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p. 1043 - 1047
(2007/10/03)
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- Medium Effects in Unsymmetrical Disulfides Compounds. Synthesis from Bunte Salts
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The present study allows us to show the influence of the polarity of the reaction medium as well as the electron-donating and withdrawing character of para substituents of α-halogeno toluenes in the preparation of unsymmetrical disulfides using the Bunte
- Hiver, Patricia,Dicko, Amadou,Paquer, Daniel
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p. 9569 - 9572
(2007/10/02)
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- Kinetics of Reaction of Benzyl Chloride with Thiosulphate in Presence of Surfactants
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The kinetics of the reaction of benzyl chloride with sodium thiosulphate has been studied in the presence of varying concentrations of surfactants like cetyltrimethylammonium bromide (CTAB) and sodium dodecyl sulphate (NaLS) in 40:60 methanol-water at 35 deg C.The reaction follows total second order kinetics and the second order rate constant (k2) increases with increasing but decreases with increasing .At a fixed or the values of k2 decrease when (i) is increased at constant , (ii) is increased at constant and (iii) both and are increased proportionately.Plausible explanation for these observations are given.The kinetic results have been fitted to some model equations and discussed.
- Das, B. N.,Sinha, B. K.
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p. 723 - 725
(2007/10/02)
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