7651-02-7Relevant articles and documents
Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
Agafonova, Mariya N.,Chirkova, Milana N.,Druk, Anastasia Y.,Grishaev, Denis Y.,Kayumov, Airat R.,Kazakova, Renata R.,Krylova, Elena S.,Nikishova, Tatyana V.,Nikitina, Elena V.,Sabirova, Alina E.,Sapozhnikov, Sergey V.,Shtyrlin, Nikita V.,Shtyrlin, Yurii G.
, (2021/01/06)
A diverse series of 43 novel “soft antimicrobials” based on quaternary ammonium pyridoxine derivatives which include six-membered acetals and ketals of pyridoxine bound via cleavable linker moieties (amide, ester) with a fragment of fatty carboxylic acid was designed. Nine compounds exhibited in vitro promising antibacterial activity against Gram-positive and Gram-negative bacterial strains with MIC values comparable with reference antiseptics miramistin, benzalkonium chloride and chlorohexidine. On various clinical isolates, the lead compounds 6i and 12a exhibited antibacterial activity comparable with that of benzalkonium chloride while higher than that of miramistin. Moreover, 6i and 12a were able to kill bacteria embedded into the matrix of mono- and dual species biofilms. The treatment of bacterial cells by either 6i and 12a lead to fast depolarization of the membrane suggesting that the membrane is an apparent molecular target of compounds. 6i and 12a were non mutagenic neither in SOS-chromotest nor in Ames test and non-toxic in vivo at acute oral (LD50 > 2000 mg/kg) and cutaneous administration (LD50 > 2500 mg/kg) on mice. Taken together, our data allow suggesting described active compounds as promising starting point for the new antibacterial agents development.
Synthesis, Characterization, and Viscosification of Amidosulfobutaine and Zwitterionic Gemini Surfactants
Mansha, Muhammad,Ullah, Nisar,Kalgaonkar, Rajendra A.,Baqader, Nour
, p. 697 - 706 (2020/12/01)
The viscoelastic surfactants (VES)-based acid diverters are frequently used to divert acid flow from high-permeability layers into low-permeability for enhanced overall productivity of the treated well. In general, an optimum VES-based system possesses advantages of decrease in absorption loss, damage of reservoir, and improved adaptability of active agents to high salinity. Herein, we report the synthesis of three new zwitterionic gemini surfactants (1–3) and previously known amidosulfobutaine (C18AMP3SB) has been accomplished for the investigation of diverting acid performance. The synthesis of these surfactants was achieved by the amidation of the acid chlorides of commercially available fatty acids with 3-(dimethylamino)-1-propylamine followed by subsequent reactions with appropriate sultone or ethyl 4-bromobutanoate. The synthesized surfactants were well characterized by spectroscopic methods including IR and NMR spectroscopy. The thermogravimetric analysis (TGA) results suggested that surfactants (1–3) and C18AMP3SB possess excellent thermal stability, with no appreciable loss of mass up to 300°C. The viscosity measurements of the neat surfactants (1–3) and C18AMP3SB were performed under various temperatures, in the presence of different concentration of calcium chloride salt with the aid shear viscosimetry. The analysis revealed that the viscosity of neat C18AMP3SB increases with increase in concentration of CaCl2. With 10% CaCl2 solution, the viscosity was increased from 7.5 to 33.55 cPs, whereas in 20% CaCl2 the viscosity reached to 102 cPs with rise in temperature from ambient to 90°C. Moreover, the viscosity of neat surfactants (1–3) did not exhibit any appreciable viscosity change under the experimental conditions. However, the mixture of surfactants (1–3) each in combination with C18AMP3SB (1:1) displayed significant upsurge in the viscosity, up to more than 10 folds.
METHOD FOR PREPARING A FATTY AMIDOALKYLDIALKYLAMINE
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Page/Page column 9-10, (2021/12/08)
The present invent ion concerns a method for preparing a fatty amidoalkyldialkylamine by reacting a fatty acid with a dialkylaminoalkylamine, using a molar ratio of said dialkylaminoalkylamine to said fatty acid of more than 1 and up to 1.5, in the presence of Candida antarctica lipase as catalyst.