Derivatives Of N-benzylideneaniline Research Articles

Synthesis, structure-activity relationships and preliminary mechanism study of N-benzylideneaniline derivatives as potential TLR2 inhibitors

Toll-like receptor 2 (TLR2) can recognize pathogen-associated molecular patterns to defense against invading organisms and has been represents an attractive therapeutic target. Until today, none TLR2 small molecule antagonist have been developed in clinical trial. Herein, we designed and synthesized 50 N-benzylideneaniline compounds with the help of CADD. And subsequent in vitro studies leading to the optimized compound SMU-A0B13 with most potent inhibitory activity to TLR2 (IC50=18.21 ± 0.87 μM). Preliminary mechanism studies indicated that this TLR2 inhibitor can work through the NF-κB signaling pathway with high specificity and low toxicity, and can also efficiently downregulate inflammatory cytokines, such as SEAP, TNF-α and NO in HEK-Blue hTLR2, human PBMC and Raw 264.7 cell lines. Additionally, the docking situation also indicate SMU-A0B13 can well bind to the TLR2-TIR (PDB: 1FYW) active domain, which probably explains the bioactivity.

Formation of α-Amino Ketones: Addition of Acylzirconocene Chlorides to Imines Catalyzed by Yb(OTf)3/TmsOTf and Brønsted Acids and Three-Component Reactions of Acylzirconocene Chlorides, Aldehydes, and Amines

A direct preparation of α-amino ketone derivatives through treatment of acylzirconocene chlorides with N-benzylideneaniline derivatives, in which acylzirconocene chlorides react as “unmasked” acyl anion donors, was carried out under Yb(OTf)3/TMSOTf-catalyzed conditions. The same reactions were also carried out with the use of Bronsted acids as catalyst in place of Yb(OTf)3/TMSOTf. The operationally simple three-component reaction with aldehydes, anilines, and acylzirconocene chlorides affords α-amino ketone derivatives essentially in the absence of a catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Yb(OTf) 3–TMSOTf-catalyzed reactions of acylzirconocene chloride to imines

Direct access of α-amino ketone derivatives through reactions of acylzirconocene chlorides with derivatives of N-benzylideneaniline, in which acylzirconocene chlorides react as an ‘unmasked’ acyl anion donor, was carried out for the first time under Yb(OTf) 3–TMSOTf-catalyzed conditions.

Mesophases Induced in the Binary Systems Consisting of the 4-Dimethylamino-4-Alkoxy and 4-Nitro-4-Alkoxy Derivatives of N-Benzylideneaniline

Mesophases Induced in the Binary Systems Consisting of the 4-Dimethylamino-4-Alkoxy and 4-Nitro-4-Alkoxy Derivatives of N-Benzylideneaniline

Mesophases Induced in the Binary Systems Consisting of the 4-Dimethylamino-4-Alkoxy and 4-Nitro-4-Alkoxy Derivatives of N-Benzylideneaniline

Abstract The effect of terminal alkoxyl group on the induction of mesophases has been examined by preparing phase diagrams for binary systems of potentially mesogenic 4-dimethylamino and 4-nitro derivatives of N-benzylideneaniline. All the systems composed of the methoxy and ethoxy derivatives produce a nematic phase, while both a nematic and a smectic phases are found when at least one of the component compounds carries a propoxyl group. The only exception is N-[(4-dimethylamino)benzylidene]-4-ethoxyaniline-N-(4-nitrobenzylidene)-4-propoxyaniline system which exhibits a smectic phase alone. The maximum temperature of the nematic-isotropic transition point curve is not very sensitive to the exchange in the positions of the terminal groups, especially those in the donor molecules. On the other hand, the thermal stabilities of the induced smectic phase and solid complex are markedly affected by the positions of the terminal groups.

Liquid Crystal Formation in Binary Systems. VII. Liquid Crystals Induced in N-[4-(Dimethylamino)benzylidene]-4-alkoxyaniline-4,4′-Dinitrobiphenyl and Related Systems

Abstract By the addition of 4,4′-dinitrobiphenyl to nonmesogenic 4-(dimethylamino)-4-alkoxy derivatives of N-benzylideneaniline, smectic liquid crystals could be induced. This dinitro compound induces liquid crystals more pronouncedly than N-(4-nitrobenzylidene)-4-nitroaniline and 4,4′-dinitroazoxybenzene do when the alkoxyl group in the donor molecule is methoxyl or ethoxyl, while it induces less pronouncedly when the alkoxyl group is propoxyl. 4,4′-Dicyanobiphenyl gives a metastable nematic liquid crystal when it is mixed with N-[4-(dimethylamino)benzylidene]-4-propoxyaniline and a metastable smectic liquid crystal with N-(4-propoxybenzylidene)-4-(dimethylamino)aniline. Moreover, liquid crystals are formed in the binary systems of N,N,N′,N′-tetramethylbenzidine with 4-nitro-4-alkoxy derivatives of N-benzylideneaniline. They are metastable but cover rather wide composition ranges. The examination of the layer spacing of the smectic A phase revealed that the induced phase is a monolayer liquid crystal.

Liquid Crystal Formation in Binary Systems. VI. Smectic Liquid Crystals Induced in N-[4-(Diethylamino)benzylidene]-4-ethoxyaniline-N-(4-Nitrobenzylidene)-4-ethoxy-aniline and Related Systems

Abstract The replacement of the dimethylamino group in the combinations of the 4-dimethylamino-4-alkoxy and 4-nitro-4-alkoxy derivatives of N-benzylideneaniline by a diethylamino group favors the induction of smectic phases in their mixtures.

An infrared study of the C=N stretching frequency in N-benzylideneaniline derivatives.

A series of 131 N-benzylideneaniline derivatives was prepared, and their infrared spectra were measured in the same conditions. Statistical tests showed that differences of substitution in benzene ring of benzylidene group affected acceptably on the region of C=N stretching absorption peak, but those in benzene ring of aniline group had smaller effect on it.