4079-68-9Relevant articles and documents
Synthesis, surface properties and bioactivity of novel 4-Substituted 1,2,3-Triazole quaternary ammonium surfactants
Mechken, Karima Amel,Menouar, Mohammed,Belkhodja, Moulay,Saidi-Besbes, Salima
, (2021/07/09)
Series of novel 1,2,3-triazole based quaternary ammonium surfactants with different hydrophobic chain length and head group substituents were synthetized and characterized. Their surface properties and aggregation behavior were discussed on the basis of tensiometry and conductimetry measurements by using several parameters, including critical micelle concentration (CMC), surface tension at the cmc (γcmc), adsorption efficiency (pC20), effectiveness of surface tension reduction (Πcmc), minimum surface area occupied by a molecule (Amin) at the air ? water interface and standard Gibbs free energy of micellization ΔGMic0. These heterocyclic surfactants exhibit much lower CMC values as compared with those reported for conventional alkyltriethyl ammoniums and alkylbenzyldiethyl ammonium salts. Their micelles formation and surface adsorption in aqueous media can be tuned out through a suitable choice of the substituent attached to the polar head. Triethyl ammonium (CnTzTEA] and diethylbenzyl ammonium surfactants (CnTzBz) showed improved micellization behavior than tetradecyl diethyl ammonium (CnTzC14) homologous. The in vitro antimicrobial activity of the surfactants against B. subtilis, P. aerugenosa and A.niger strains was also investigated. CnTzBz series possessing benzyl chain showed better activity against all the tested microorganisms with minimum inhibitory concentration ranging from 6 to 57 μmol/L.
Design, synthesis and biological activities of novel pleuromutilin derivatives with a substituted triazole moiety as potent antibacterial agents
Zhang, Zhe,Li, Kang,Zhang, Guang-Yu,Tang, You-Zhi,Jin, Zhen
, (2020/07/30)
A series of novel pleuromutilin derivatives possessing 1,2,3-triazole moieties were synthesized via click reactions under mild conditions. The in vitro antibacterial activities of these derivatives against 4 strains of S. aureus (MRSA ATCC 43300, ATCC 29213, AD 3, and 144) and 1 strain of E. coli (ATCC 25922) were tested by the broth dilution method. The majority of the synthesized derivatives displayed potent antibacterial activities against MRSA (MIC = 0.125–2 μg/mL). It was also found that most compounds had no significant inhibitory effect on the proliferation of RAW264.7 cells at the concentration of 8 μg/mL. Among these derivatives, compound 32 (～1.71 log10 CFU/g) containing dimethylamine group side chain displayed more effective than tiamulin (～0.77 log10 CFU/g) at the dose of 20 mg/kg in reducing MRSA load in thigh infected mice. Additionally, compound 32 (the survival rate was 50%) also displayed superior in vivo efficacy to that of tiamulin (the survival rate was 20%) in the mouse systemic model. Structure-activity relationship (SAR) studies resulted in compound 32 with the most potent in vitro and in vivo antibacterial activity among the series. Moreover, compound 32 was evaluated in CYP450 inhibition assay and showed moderate in vitro inhibition of CYP3A4 (IC50 = 6.148 μM).
Assembly of Functionalized 4-Alkynylisoxazoles by Palladium-Catalyzed Three-Component Cascade Cyclization/Alkynylation
Li, Jianxiao,Huang, Ruikang,Li, Can,Lin, Shao,Wu, Wanqing,Jiang, Huanfeng
, p. 2309 - 2315 (2019/06/24)
A novel N-heterocyclic carbene (NHC)-palladium-catalyzed three-component cascade cyclization/alkynylation for the synthesis of structurally diverse 4-alkynylisoxazoles was efficiently developed in ionic liquids. The operational simplicity, without additives, no additional ligands, and 0.5 mol % catalyst loading under air are some of the attractive features of this present protocol.
