19437-45-7Relevant academic research and scientific papers
Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations
Bucio-Cano, Alejandro,Reyes-Arellano, Alicia,Correa-Basurto, José,Bello, Martiniano,Torres-Jaramillo, Jenifer,Salgado-Zamora, Héctor,Curiel-Quesada, Everardo,Peralta-Cruz, Javier,Avila-Sorrosa, Alcives
, p. 7565 - 7577 (2015/12/18)
To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere-protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series.
RNA cleavage catalyzed by amphoteric bis(acyl)guanidinium derivatives
Goebel, Michael W.,Roussev, Christo D.,Scheffer, Ute
, p. 215 - 227 (2014/03/21)
Described herein are two series (twelve compounds each) of very closely related guanidinium-based receptors and their ability to catalyze hydrolytic cleavage of a unique RNA substrate - oligo-dT flanked trans-Activation Responsive region of the HIV-1 mRNA, TAR RNA. The significant difference in activities of otherwise very similar compounds is discussed, and direct and indirect evidences supporting our interpretation are presented. The results indicate that improvements in catalytic efficiency could be achieved with little modification of the structure of a relatively weak catalyst, and that a crucial feature could be a finely calibrated interplay between anion-binding and proton-donating abilities. Copyright
Efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles with aminoiminomethanesulfonic acid derivatives
Mohanazadeh, Farajollah,Nami, Navabe,Hosseini, Samine Sadat
experimental part, p. 1055 - 1058 (2012/01/04)
A highly efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles from aminoiminomethanesulfonic acid derivatives is described. The method is simple and practical, generating imidazoline and benzimidazoline derivatives in excellent isolated yields.
Novel heterocyclic derivatives bearing an amino radical, processes for their production and the pharmaceutical compositions containing them
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, (2008/06/13)
This invention relates to novel heterocyclic derivatives bearing an amino group and to processes for making said compounds. More particularly this invention provides novel heterocyclic compounds the hetero ring of which has two hetero atoms, the same or different, substituted with a free or substituted amino group. These compounds are useful as active ingredients of drugs.
Synthesis of Guanidino-1,3,5-triazines Using DMF
Iio, Kokoro,Ichikawa, Eiichi
, p. 2735 - 2736 (2007/10/02)
2,4,6-Triguanidino-1,3,5-triazine and 2,4,6-tris(3-methylguanidino)-1,3,5-triazine were synthesized in 42 and 52percent yields, respectively, by the cyclotrimerization of cyanoguanidine and 1-methyl-3-cyanoguanidine using DMF as a solvent in the presence of hydrogen chloride. 1-Phenyl-3-cyanoguanidine, 1,2-dimethyl-3-cyanoguanidine, and 2-imidazolidinylidenecyanamide, however, were cyclodimerized to the corresponding guanidino-1,3,5-triazines in a similar manner.
