67036-13-9Relevant articles and documents
Biological evaluation and docking studies of new carbamate, thiocarbamate, and hydrazide analogues of ACYL homoserine lactones as vibrio fischeri-quorum sensing modulators
Zhang, Qiang,Queneau, Yves,Soulère, Laurent
, p. 1 - 12 (2020/05/25)
A series of carbamate, thiocarbamate, and hydrazide analogues of acylhomoserine lactones (AHLs) were synthesized and their ability to modulate Vibrio fischeri-quorum sensing was evaluated. The compounds in the series exhibit variable side chain length and the possible presence of a diversely substituted phenyl substituent. Biological evaluation on the Vibrio fischeri quorum sensing system revealed that the ethyl substituted carbamate (1) display a weak agonistic activity whereas compounds with longer chain length or benzyl substituents display significant antagonistic activity. The most active compounds in the series were the 4-nitrobenzyl carbamate and thiocarbamate 7 and 11 which exhibited an IC50 value of about 20 μM. These activities are in the range of other reported of AHL-structurally related quorum sensing (QS) inhibitors. Docking experiments conducted on the LuxR model showed that, compared to the natural ligand OHHL, the additional heteroatom of the carbamate group induces a new hydrogen bond with Tyr70 leading to a different global hydrogen-bond network. Tyr70 is an important residue in the binding site and is strictly conserved in the LuxR family. For the 4-nitrobenzyl carbamate and thiocarbamate analogues, the docking results highlight an additional hydrogen bond between the nitro group and Lys178. For hydrazide analogues, which are deprived of any activity, docking shows that the orientation of the carbonyl group is opposite as compared with the natural ligand, leading to the absence of a H-bond between the C=O with Tyr62. This suggests that, either this later interaction, or the influence of the C=O orientation on the overall ligand conformation, are essential for the biological activity.
PHARMACEUTICAL COMPOSITION COMPRISING PHENYLAMIDINE DERIVATIVE AND METHOD OF USING THE PHARMACEUTICAL COMPOSITION IN COMBINATION WITH ANTIFUNGAL AGENT
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, (2009/07/10)
A pharmaceutical composition comprising a phenylamidine derivative or a salt thereof, represented by a general formula, wherein R1 and R2 may be same or different, and represent an optionally substituted C3-4alkyl group; a
REACTION OF ORGANIC CARBONATES WITH AMINES I. REACTION OF ALKYL PHENYL CARBONATES WITH PRIMARY ALIPHATIC AMINES
Mikheev, V. V.,Svetlakov, N. V.,Garipov, R. M.
, p. 215 - 220 (2007/10/02)
The reaction of alkyl phenyl carbonates with primary aliphatic amines, leading to the formation of N-alkylurethanes, was investigated.The reaction has overall third order, which is explained by the catalytic action of the amine.The effect of the structure of the alkyl radical and the character of the substituent in the phenyl group of the alkyl phenyl carbonates and also the effect of the polarity of the solvent on the rate of the transformation were investigated.The reaction obeys the Hammett equation.