2443-62-1Relevant articles and documents
Dynamic combinatorial libraries constructed on polymer scaffolds
Fulton, David A.
, p. 3291 - 3294 (2008)
(Figure Presented) Functionalized polymers were prepared by grafting acylhydrazides onto a polyvinylbenzaldehyde scaffold through reversible hydrazone linkages. The dynamic nature of these linkages allows the functionalized polymers to exchange and reshuffle their appendages, and the resultant mixture of polymers can be considered as a dynamic combinatorial library constructed upon a polymer scaffold. The dynamic nature of these functionalized polymers was demonstrated.
Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides
Wu, Dehua,Song, Jintong,Qu, Lang,Zhou, Weilan,Wang, Lei,Zhou, Xiangge,Xiang, Haifeng
, p. 3370 - 3378 (2020/10/02)
The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.
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.
Micromolecular gelator, gel material, preparation method and application
-
Paragraph 0060; 0065; 0066, (2018/11/22)
The invention provides a micromolecular gelator, a gel material, a preparation method and an application. The gelator is prepared by taking cheap and easily available phenyllactic acid as a raw material and introducing a hydrazide group and a hydrophobic alkyl chain through a simple and mature chemical reaction. The gelator can effectively gelate various organic solvents; the gel material formed by the gelator and methyl benzoate can quickly and efficiently remove phenol from sewage; the gelator can selectively gelate petroleum products such as gasoline, diesel oil, kerosene and lubricating oil, and crude oil in an oil-water mixture without the help of an additive; oil and water separation is achieved by simple operation; the gelator can be used for leakage management of the crude oil andthe petroleum products and is multifunctional; and in addition, the gelator has good recyclability and very good application prospects in the fields of phenol removal from the sewage, marine oil spilltreatment and the like.
Multiple Hydrogen Bonds Promoted ESIPT and AIE-active Chiral Salicylaldehyde Hydrazide
Wang, Man,Cheng, Caiqi,Song, Jintong,Wang, Jun,Zhou, Xiangge,Xiang, Haifeng,Liu, Jin
, p. 698 - 707 (2018/06/06)
The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules (41 samples) have been designed and prepared. Even though these soft materials contain a very small π-conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited-state intramolecular proton-transfer (ESIPT) to display strong blue, green, yellow, and orange aggregation-induced emission (AIE) with large Stokes shifts (up to 184 nm) and high fluorescence quantum yields (Ф up to 0.20). Unusual mechanochromic fluorescence enhancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2+ (Ф up to 0.46) probes, universal anion (Ф up to 0.14) and unprotected amino acids (Ф up to 0.16) probes, and chiral diamine (enantiomeric selectivity and Ф up to 0.36 and 0.062, respectively) receptors. Combining their advantages of AIE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AIE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple-stimuli-responsive smart materials.
Asymmetric Synthesis and Antitumor Activity of Spiro-Oxadiazole Derivatives from 1,4:3,6-Dianhydro-D-fructose
Xu, Wenke,Ge, Yongxun,Hou, Yu,Liu, Yingju,Hua, Yingchun,Han, Weiwei,Qin, Zhiyan,Liu, Fengwu
, p. 1437 - 144 (2017/10/06)
A series of spiro-oxadiazoles were synthesized from 1,4:3,6-dianhydro-D-fructose and hydrazides via a stereo- selective two-step reaction sequence. The structures of newly synthesized compounds were established by spectral analysis. The absolute configuration of compound 2a was further confirmed by single crystal X-ray analysis. All the synthesized compounds were screened for their in vitro antitumor activity, showing that these compounds have poor inhibitory activities against A549, MGC-803 tumor cells.
PREPARING METHOD OF HYDRIZIDE COMPOUNDS
-
Paragraph 0128; 0176-0178, (2017/01/02)
The present invention relates to a method for preparing hydrazide and, more specifically, to a method for preparing a hydrazide derivative compound by reacting a hydrazine-carbon dioxide coupled compound with an organic acid or sulfonic acid compound.COPYRIGHT KIPO 2015
Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients
De Azevedo, Ricardo Alexandre,Ferreira, Adilson Kleber,Jorge, Salomo Dria,Palace-Berl, Fanny,Pasqualoto, Kerly Fernanda Mesquita,Silva, Marcelo Nunes,Tavares, Leoberto Costa,Teixeira, Sarah Fernandes,Zingales, Bianca,Zorzi, Rodrigo Rocha
, p. 330 - 339 (2015/04/27)
Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was Ng€2-((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 ± 0.12 μM; 3.17 ± 0.32 μM; and 1.81 ± 0.18 μ4M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease.
COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT
-
Page/Page column 40, (2015/04/15)
Embodiments of the present disclosure provide for compositions including an antimicrobial agent, pharmaceutical compositions including the antimicrobial agent, methods of treatment of an infection, methods of treatment using compositions or pharmaceutical
Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
Neumann, Donna M.,Cammarata, Amy,Backes, Gregory,Palmer, Glen E.,Jursic, Branko S.
, p. 813 - 826 (2014/01/23)
Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.
