67036-13-9Relevant academic research and scientific papers
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.
Orchestrating Directional Molecular Motions: Kinetically Controlled Supramolecular Pathways of a Helical Host on Rodlike Guests
Wang, Xiang,Wicher, Barbara,Ferrand, Yann,Huc, Ivan
, p. 9350 - 9358 (2017/07/22)
An aromatic oligoamide sequence was designed to fold and self-assemble into a double helical host having a cylindrical cavity complementary to linear oligocarbamate guests. Formation of helical pseudorotaxane complexes, foldaxanes, between the host and guests having binding stations of different affinities was evidenced by NMR and X-ray crystallography. Rodlike guests possessing two or three binding stations, long alkyl or oligoethylene glycol spacers or bulky barriers in-between the binding stations, and a single bulky stopper at one end were synthesized. Kinetic investigations of the threading and translation of the double helix along multistation rods were monitored by 1H NMR. Results show that multiple events may occur upon sliding of the host from the nonbulky end of the rod to reach the thermodynamically most stable state before unfolding-mediated dissociation has time to take place, including binding on intermediate stations and rapid sliding along nonbinding spacers. Conversely, installing a kinetic barrier that blocks sliding allows for the deliberate integration of a helix dissociation reassociation step in the supramolecular trajectory. Typical sliding processes can be monitored over the course of hours whereas steps involving unwinding-rewinding of the helix proceeded over the course of days. These results further demonstrate the interest in foldaxanes to design complex sequences of supramolecular events within networks of equilibria through the adjustment of the kinetics of the individual steps involved.
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
NOVEL ARYLAMIDINE DERIVATIVE, SALT THEREOF AND ANTIFUNGAL AGENT CONTAINING THOSE
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Page/Page column 19-20, (2008/12/08)
Disclosed is an arylamidine derivative represented by the following general formula: (wherein R1 and R2 independently represent an optionally substituted C3-4 alkyl group) or a salt thereof, which is useful as an antifunga
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.
