- Lipophilic vancomycin aglycon dimer with high activity against vancomycin-resistant bacteria
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Antibiotic-resistant superbugs such as vancomycin-resistant Enterococci (VRE) and Staphylococci have become a major global health hazard. To address this issue, we synthesized vancomycin aglycon dimers to systematically probe the impact of a linker on biological activity. A dimer having a pendant lipophilic moiety in the linker showed ~300-fold more activity than vancomycin against VRE. The high activity of the compound is attributed to its enhanced binding affinity to target peptides which resulted in improved peptidoglycan (cell wall) biosynthesis inhibition. Therefore, our studies suggest that these compounds, prepared by using facile synthetic methodology, can be used to combat vancomycin-resistant bacterial infections.
- Yarlagadda, Venkateswarlu,Sarkar, Paramita,Manjunath, Goutham B.,Haldar, Jayanta
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supporting information
p. 5477 - 5480
(2015/11/18)
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- Preparation of N-alkylbis(3-aminopropyl)amines by the catalytic hydrogenation of N-alkylbis(cyanoethyl)amines
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(Chemical Equation Presented) An improved process for the preparation of N-alkylbis(3-aminopropyl)amines is described. These triamines are of interest as monomers for the condensation polymerization with esterified carbohydrate diacids (aldaric acids) to generate the corresponding poly(4-alkyl-4- azaheptamethylene aldaramides). The triamine synthesis is comprised of two efficient steps and requires no chromatographic purification. Bisconjugate addition of alkylamines to acrylonitrile followed by catalytic hydrogenation of the N-alkylbis(cyanoethyl)amines over Raney nickel yields the target N-alkylbis(3-aminopropyl)amines. Much less solvent was used in the bisconjugate addition step then previously reported, and in the second step, a relatively low-pressure catalytic hydrogenation (50 psi of hydrogen) was employed using Raney nickel as the catalyst in a 7 N methanolic ammonia solvent system to afford the N-alkylbis(3-aminopropyl)amines of high purity in nearly quantitative yield.
- Denton, Travis T.,Joyce, Abigail S.,Kiely, Donald E.
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p. 4997 - 5000
(2008/02/05)
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- Bis-betaines, a process for their preparation, and cleaning agents containing these compounds
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Bis-betaines of the formula STR1 in which R denotes a saturated or an olefinically unsaturated hydrocarbon radical which has 1 to 3 double bonds and 8 to 22 carbon atoms, n1 and n2 represent an integer from 2 to 3, and n1 and n2 can be identical or different, m1 and m2 represent an integer from 1 to 4, and m1 and m2 can be identical or different, and a, b, c and d, which are identical or different, each is a number from 1 to 5, but the sum (a+b+c+d) should be at most 10. The compounds are prepared from primary amines of the formula RNH2, by dicyanoalkylation, hydrogenation, ethoxylation and reaction with alkali metal salts of ω-halogenocarboxylic acids. They are suitable for formluating cosmetic and industrial cleaning agents.
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- Triamine-trioxides, a process for their preparation, and cleaning agents containing these compounds
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Triamine-trioxides of the formula STR1 in which R denotes a saturated or an olefinically unsaturated hydrocarbon radical which has 1 to 3 double bonds and 8 to 22 carbon atoms, n1 and n2 represent an integer from 2 to 3, and n1 and n2 can be identical or different, and a, b, c and d, which are identical or different, each is a number from 1 to 5, with the proviso that the sum (a+b+c+d) should be at most 10. The compounds are prepared from primary amines of the formula RNH2 by dicyanoalkylation, hydrogenation, ethoxylation and oxidation with hydrogen peroxide. They are suitable for formulating industrial and also cosmetic cleaning agents.
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- Bis-betaine-amine oxides, process for their preparation, and cleaning agents containing them
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Bis-betaine-amine oxides of the formula STR1 in which R is a saturated or an olefinically unsaturated hydrocarbon radical having 1 to 3 double bonds and 8 to 22 carbon atoms, n1 and n2 each is an integer of from 2 to 3, n1 and n2 optionally being identical or different, m1 and m2 each is an integer of from 1 to 4, m1 and m2 optionally being identical or different, and a, b, c and d, being identical or different, each is a number of from 1 to 5, with the proviso that the sum (a+b+c+d) is at most 10. The compounds are prepared from primary amines of the formula RNH2, by dicyanoalkylation, hydrogenation, ethoxylation, reaction with alkali metal salts of ω-halocarboxylic acids, and subsequent oxidation with hydrogen peroxide. They are surfactants of mild action and suitable for formulating cosmetic and industrial cleaning agents.
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