112-16-3Relevant articles and documents
Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D
Yang, Hong Woon,Zhao, Cunxiang,Romo, Daniel
, p. 16471 - 16488 (1997)
A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) - Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal.
DECOMPOSITION DE L'ACIDE PEROXYDODECANOIQUE DANS CCl4: ROLE DU SOLVANT
Sorba, J.,Fossey, J.,Lefort, D.,Nedelec, J. Y.
, p. 69 - 74 (1981)
The decomposition of peroxydodecanoic acid in refluxing CCl4 proceeds by a complex process involving ionic and radical reactions.In the latter, this study has confirmed the important role, shown previously, of the character (nucleophilic or electrophilic) of the radical on the regioselectivity of the attack on the peracid. The (*)CCl3 radicals (electrophilic) proceed by abstraction of the H of the peracid; the analysis of the products confirms the presence of intermediary R-(*)CO radicals resulting from the equilibrium: This explains why the decomposition of a peracid in CCl4 leads mainly to the formation of the corresponding acid whereas in a hydrocarbon solvent one observes essentially the decarboxylation leading to the alcohol according to the mechanism previously proved.
Synthesis of neoglycolipids based on D-lactose
Gur'eva,Budanova,Sebyakin
, p. 173 - 177 (2009)
A synthesis was performed of amphiphilic D-lactose derivatives differing by the length and number of aliphatic chains. The compounds may be applied to the carbohydrate modification of phosphatidylcholine liposomes.
Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition
Boger, Dale L.,Sato, Haruhiko,Lerner, Aaron E.,Austin, Bryce J.,Patterson, Jean E.,Patricelli, Matthew P.,Cravatt, Benjamin F.
, p. 265 - 270 (1999)
The examination of a series of trifluoromethyl ketone inhibitors of Fatty Acid Amide Hydrolase (FAAH, oleamide hydrolase, anandamide amidohydrolase) is detailed in efforts that define structural and conformational properties that contribute to enzyme inhibition and substrate binding. The results imply an extended bound conformation, highlight a role for the presence, position, and stereochemistry of a Δ cis double bond, and suggest little apparent role for C11-C18/C22 of the fatty acid amide substrates.
Liquid crystalline and light emitting polyacetylenes: Synthesis and properties of biphenyl-containing poly(1-alkynes) with different functional bridges and spacer lengths
Lam, Jacky W.Y.,Dong, Yuping,Cheuk, Kevin K.L.,Luo, Jingdong,Xie, Zhiliang,Kwok, Hoi Sing,Mo, Zhishen,Tang, Ben Zhong
, p. 1229 - 1240 (2002)
Biphenyl-(Biph-) containing 1-alkynes (3 and 4) and their polymers (1 and 2) with varying bridge groups and spacer lengths were synthesized and the effects of the structural variation on their properties, especially their mesomorphism and photoluminescence behaviors, were studied. The acetylene monomers 3(3) [HC≡C(CH2)3O-Biph-OCO(CH2)10CH 3] and 4(m) [HC≡C(CH2)m OCO-Biph-OCO(CH2)10-CH3, m = 3,4] were prepared by sequential etherization and esterification reactions of 1-alkynes. While 3(3) exhibits enantiotropic crystal E and SmB mesophases, its structural cousin 4(3) displays only monotropic SmB phase. Enantiotropic SmA and SmB mesophases are, however, developed when the spacer length is increased to 4. Polymerizations of the monomers are affected by Mo-, W-, Rh-, and Fe-based catalysts, with the WCl6-Ph4Sn catalyst giving the best results (isolation yield up to 85% and Mw up to 59000). The polymers were characterized by IR, UV, NMR, TGA, DSC, POM, XRD, and PL analyses. Compared to 1(3), 2(3) shows a red-shifted absorption, a higher Ti, and a better packed interdigitated bilayer SmAd structure, while the mesophase of 2(4) involves mionolayer-packing arrangements of the mesogens. Upon photoexcitation, 1(3) emits almost no light but 2(m) gives a strong ultraviolet emission (λmax ～ 350 nm), whose intensity increases with the spacer length.
A new method for the synthesis of 5-fluorouracil prodrugs
Jolima?tre, Pascale,André-Barres, Christiane,Malet-Martino, Myriam,Martino, Robert,Rico-Lattes, Isabelle
, p. 1829 - 1831 (1999)
Bromo-tris(dimethylamino)-phosphonium-hexafluorophosphate (BROP) is a particularly suitable reagent for synthesising some 5-fluorouracil prodrugs in a one step reaction. Several acids, especially retinoic acid, were bound to the N1 of 5-fluorou
A novel α-aminophosphonic acid-modified acrylamide-based hydrophobic associating copolymer with superb water solubility for enhanced oil recovery
Gou, Shaohua,Zhang, Qin,Yang, Cheng,Li, Qing,Xu, Shuhui,Wu, Yuanpeng,Guo, Qipeng
, p. 76696 - 76706 (2016)
As a non-renewable resource, the rational exploitation of oil has attracted a large amount of attention. Among many methods for enhanced oil recovery, polymer flooding is the most suitable method of chemical flooding for non-marine reservoirs and therefore various modified acrylamide-based copolymers have been studied. In this study, a novel α-aminophosphonic acid-modified hydrophobic associating copolymer was successfully synthesized by copolymerization of acrylamide, acrylic acid, N-allyldodecanamide and 1-(dimethylamino)allylphosphonic acid. The copolymer was characterized by FT-IR, 1H NMR and thermogravimetry and exhibited superior water solubility and thickening capability. Subsequently, the shear resistance, temperature resistance and salt tolerance of the copolymer solution were investigated. The value of apparent viscosity retention of a 2000 mg L-1 copolymer solution was as high as 58.55 mPa s at a shear rate of 170 s-1 and remained at 40.20 mPa s at 120 °C. The values of apparent viscosity retention of 55.41 mPa s, 59.95 mPa s and 52.97 mPa s were observed in solutions of 10000 mg L-1 NaCl, 1200 mg L-1 MgCl2, and 1200 mg L-1 CaCl2, respectively. These were better than those of partially hydrolyzed polyacrylamide under the same conditions. In addition, an increase of up to 14.52% in the oil recovery rate compared with that for water flooding could be achieved in a core flooding test using a 2000 mg L-1 copolymer solution at 65 °C.
Bioresponsive deciduous-charge amphiphiles for liposomal delivery of DNA and siRNA
Pierrat, Philippe,Kereselidze, Dimitri,Wehrung, Patrick,Zuber, Guy,Pons, Francoise,Lebeau, Luc
, p. 1362 - 1379 (2013)
Purpose: Biolabile cationic lipids were developed for efficient intracellular delivery of DNA and siRNA. Methods: The compounds have been designed starting from the membrane lipid DOPC in a way they may loose their cationic charge when exposed to an acidic and/or enzymatic stimulus, such as those met during the journey of a lipoplex in biological media. Results: They demonstrated remarkable efficiency to deliver DNA in various cell lines (BHK-21, Calu-3, NCI-H292, and A549), with no significant cytotoxicity. Furthermore, two of the compounds (carbonate-based DOPC derivatives) revealed able to deliver small interfering RNA in U87Luc and A549Luc cancer cells and to mediate a selective 70-80% knockdown of the stably transfected luciferase gene. Conclusions: The results show that the described bioresponsive cationic lipids have high DNA and siARN delivery activity which is encouraging in view of delivering a therapeutic nucleic acid to pulmonary tissues in vivo.
The influence of varied amide bond positions on hydraphile ion channel activity
Weber, Michelle E.,Wang, Wei,Steinhardt, Sarah E.,Gokel, Michael R.,Leevy, W. Matthew,Gokel, George W.
, p. 177 - 184 (2006)
Hydraphile compounds have been prepared in which certain amine nitrogens have been replaced by amide residues. The amide bonds are present either in the side chain, the spacer chain, or the central relay. Sodium cation transport through phospholipid vesicles mediated by each hydraphile was assessed. All of the amide-containing hydraphiles showed increased levels of Na+ transport compared to the parent compound, but the most dramatic rate increase was observed for sidearm amine to amide replacement. We attribute this enhancement to stabilization of the sidearm in the bilayer to achieve a better conformation for ion conduction. Biological studies of the amide hydraphiles with Escherichia coli and Bacillus subtilis showed significant toxicity only with the latter. Further, the consistency between the efficacies of ion transport and toxicity previously observed for non-amidic hydraphiles was not in evidence. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
Catalyst for synthesizing acyl chloride compounds and application thereof
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Paragraph 0043-0047, (2020/10/20)
The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.
A dibenzocyclooctyne derivative and application thereof
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Paragraph 0026; 0032; 0034, (2019/07/10)
The invention relates to a dibenzocyclooctyne derivative and application thereof. The dibenzocyclooctyne derivative is especially used for carrying out click reaction with azide compounds to prepare stable 1,2,3-triazole compounds, and the latter have a wide range of uses in labeling glycans, proteins and lipids of living cells, glycoprotein enrichment of proteomics, protein and oligonucleotide modification, and tissue reconstruction engineering.
