26825-94-5Relevant articles and documents
Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow
Minozzi, Clémentine,Grenier-Petel, Jean-Christophe,Parisien-Collette, Shawn,Collins, Shawn K.
supporting information, p. 2730 - 2736 (2018/11/21)
A copper-based photocatalyst, Cu(tmp)(BINAP)BF4, was found to be active in a photoredox Appel-type conversion of alcohols to bromides. The catalyst was identified from a screening of 50 complexes and promoted the transformation of primary and secondary alcohols to their corresponding bromides and carboxylic acids to their anhydrides. The protocol was also amendable and optimized under continuous flow conditions.
Chiral self-assembly of designed amphiphiles: Optimization for nanotube formation
Barclay, Thomas G.,Constantopoulos, Kristina,Matisons, Janis G.,Zhang, Wei,Fujiki, Michiya
, p. 14172 - 14179,8 (2020/09/02)
Four amphiphiles with l-aspartic acid headgroups (Asp) and a diphenyldiazenyl group (Azo) contained within the hydrophobic tails were designed and synthesized for self-assembly into helically based nanotubes. The amphiphiles of the form R'-{4-[(4-alkylphenyl)diazenyl]phenoxy}alkanoyl-l- aspartic acid (where R' is 10 or 11) varied only in alkyl chain lengths either side of the azo group, having 4, 7, or 10 carbon distal chains and 10 or 11 carbon proximal chains (R-Azo-R'-Asp, where R denotes the number of carbons in the distal chain and R' denotes the number of carbons in the proximal chain). Despite the molecular similarities, distinct differences were identified in the chiral order of the structures self-assembled from hot methanolic aqueous solutions using microscopy and spectroscopic analyses. This was reflected in dominant thermodynamic aggregate morphologies that ranged from amorphous material for 10-Azo-10-Asp, through twisted ribbons (196 ± 49 nm pitch) for 7-Azo-11-Asp, to the desired helically based nanotubes for 4- and 7-Azo-10-Asp (81 ± 11 and 76 ± 6 nm diameters, respectively). Another key variable in the self-assembly of the amphiphiles was the use of a second method to precipitate aggregates from solution at room temperature. This method enabled the isolation of thermodynamically unstable and key transitional structures. Helical ribbons were precursor structures to the nanotubes formed from 4- and 7-Azo-10-Asp as well as the wide, flattened nanotube structures (587 ± 85 nm width) found for 4-Azo-10-Asp. Overall, the results highlighted the interplay of influence of the headgroup and the hydrophobic tail on self-assembly, providing a basis for future rational design of self-assembling amphiphiles.
INHIBITORS OF BIOFILM FORMATION OF GRAM-POSITIVE AND GRAM-NEGATIVE BACTERIA
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Page/Page column 71-72, (2009/07/18)
The present invention relates to the use of compounds as broad spectrum inhibitors of bacterial biofilm formation. In particular the invention refers to a family of compounds that block the quorum sensing system of Gram-negative and Gram-positive bacteria, a process for their manufacture, pharmaceutical compositions containing them and to their use for the treatment and prevention of bacterial damages and diseases, in particular for diseases where there is an advantage in inhibiting quorum sensing regulated phenotypes of pathogens.
Identification and total synthesis of novel fatty acids from the caribbean sponge Calyx podatypa
Carballeira, Nestor M.,Pagan, Mayra,Rodriguez, Abimael D.
, p. 1049 - 1052 (2007/10/03)
The phospholipid fatty acid composition of the Caribbean sponge Calyx podatypa was studied, and 85 different fatty acids were identified, in particular the 11-methylpentadecanoic acid and 10-tricosenoic acid, which have no literature precedence. Structural characterization was accomplished by means of gas chromatography - mass spectrometry on their corresponding methyl esters and dimethyl disulfide derivatives. The structure of 11- methylpentadecanoic acid was further confirmed by total synthesis (17% overall yield) starting from commercially available 10-hydroxydecanoic acid.
Identification and biosynthesis of (E,E) -10,12-Tetradecadienyl acetate in spodoptera littoralis female sex pheromone gland
Navarro, Isabel,Mas, Esther,Fabrias, Gemma,Camps, Francisco
, p. 1267 - 1274 (2007/10/03)
A miner component of the sex pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis, has been identified as (E,E)-10,12-tetradecadienyl acetate. Structural elucidation has been carried out by isobutane-chemical ionization mass spectrometry of the fatty acyl biosynthetic precursor-derived methyl ester. To assign the stereochemistry of the double bonds, the four isomers of both 10,12-tetradecadienyl acetates and methyl 10,12-tetradecadienoates have been synthesized and their gas chromatography retention times and mass spectra have been compared to those of the corresponding natural compounds. Mass-labeling experiments showed that the (E,E)-10,12-tetradecadienoyl moiety is biosynthetically derived from (Z)-11-tetradecenoic acid in the insect pheromone gland.
Cyclization of 9-Substituted Decanoic Acid Derivatives to 9-Decanolide and 9-Decanelactam
Bartra, Marti,Vilarrasa, Jaume
, p. 5132 - 5138 (2007/10/02)
Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedures for lactonization and lactamization at 80 deg C under identical high-dilution conditions.The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions.Analogously, treatment of S-2-pyridyl 9-azidodecanethionate with Sn(SePh)3(1-) afforded the best yield of the 10-membered lactam.The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag(1+) strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.
Synthese de lactones a cycle moyen: Application a la synthese du pentadecanolide-15 et du phoracantholide I
Cossy, Janine,Pete, Jean-Pierre
, p. 989 - 994 (2007/10/02)
Medium ring size lactones can be prepared from bifunctional commercial starting compounds in high yields, using a few step sequence.Lactonisation is obtained by cyclization of the free ω-hydroxyacids or by the cyclization of ω-hydroxyacids having the hydroxy and carboxy group protected.
Sulfur containing alkenylenyl substituted benzoic acids and phenyl tetrazoles and their use as anti-allergic agents
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, (2008/06/13)
Pharmaceutical compounds are described of the formula STR1 in which R1 is (i) R4 O(CH2 CH2 O)n (CH2)m --, where R4 is hydrogen or C1-5 alkyl, n is 0 or 1 to 5 and m is 1 to 7, or (ii) R5 --X-- where R5 is a polar group and X is a C6-20 alkylene or a C6-20 alkenylene radical containing from 1 to 3 double bonds, R2 is a group of the formula A--B-- where A is --COOH or STR2 where R6 is hydrogen or a protecting group, and B is C1-6 alkylene, and R3 is --COOH or STR3 where R7 is hydrogen or a protecting group; or a salt or ester thereof.
