50711-98-3Relevant academic research and scientific papers
Light-Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry
Chu, Chih-Wei,Stricker, Lucas,Kirse, Thomas M.,Hayduk, Matthias,Ravoo, Bart Jan
supporting information, p. 6131 - 6140 (2019/04/01)
Versatile photoresponsive gels based on tripodal low molecular weight gelators (LMWGs) are reported. A cyclohexane-1,3,5-tricarboxamide (CTA) core provides face-to-face hydrogen bonding and a planar conformation, inducing the self-assembly of supramolecular polymers. The CTA core was substituted with three arylazopyrazole (AAP) arms. AAP is a molecular photoswitch that isomerizes reversibly under alternating UV and green light irradiation. The E isomer of AAP is planar, favoring the self-assembly, whereas the Z isomer has a twisted structure, leading to a disassembly of the supramolecular polymers. By using tailor-made molecular design of the tripodal gelator, light-responsive organogels and hydrogels were obtained. Additionally, in the case of the hydrogels, AAP was coupled to the core through hydrazones, so that the hydrogelator and, hence, the photoresponsive hydrogel could also be assembled and disassembled by using dynamic covalent chemistry.
Arylazo-3,5-dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High Z-Isomer Stability, Solid-State Photochromism, and Reversible Light-Induced Phase Transition
Devi, Sudha,Kumar, Pravesh,Sah, Chitranjan,Srivastava, Anjali,Venkataramani, Sugumar
supporting information, (2019/08/21)
Reversibly photoswitchable phenylazo-3,5-dimethylisoxazole and 37 aryl-substituted derivatives were synthesized. Excellent photoswitching ability of these compounds in solution and the solid state was demonstrated. Through kinetics studies by means of NMR spectroscopy, high Z-isomer stability was demonstrated. Interestingly, the majority of the derivatives showed light-induced contrasting color changes in solution and the solid state. Besides, many of the derivatives exhibit partial phase transition upon UV irradiation. The highlight of this class of photoswitches is the reversible light-induced phase transition between solid and liquid phases in the parent compound, which can be used in patterned crystallization. These results show that this new class of azoheteroarene based photoswitches has opportunities to be useful in various domains.
Structure-Based Rational Design of Novel Inhibitors Against Fructose-1,6-Bisphosphate Aldolase from Candida albicans
Han, Xinya,Zhu, Xiuyun,Hong, Zongqin,Wei, Lin,Ren, Yanliang,Wan, Fen,Zhu, Shuaihua,Peng, Hao,Guo, Li,Rao, Li,Feng, Lingling,Wan, Jian
, p. 1426 - 1438 (2017/07/03)
Class II fructose-1,6-bisphosphate aldolases (FBA-II) are attractive new targets for the discovery of drugs to combat invasive fungal infection, because they are absent in animals and higher plants. Although several FBA-II inhibitors have been reported, none of these inhibitors exhibit antifungal effect so far. In this study, several novel inhibitors of FBA-II from C. albicans (Ca-FBA-II) with potent antifungal effects were rationally designed by jointly using a specific protocols of molecular docking-based virtual screening, accurate binding-conformation evaluation strategy, synthesis and enzymatic assays. The enzymatic assays reveal that the compounds 3c, 3e-g, 3j and 3k exhibit high inhibitory activity against Ca-FBA-II (IC50 50 value of 2.7 μM. Importantly, the compounds 3f, 3g, and 3l possess not only high inhibitions against Ca-FBA-II, but also moderate antifungal activities against C. glabrata (MIC80 = 4-64 μg/mL). The compounds 3g, 3l, and 3k in combination with fluconazole (8 μg/mL) displayed significantly synergistic antifungal activities (MIC80 0.0625 μg/mL) against resistant Candida strains, which are resistant to azoles drugs. The probable binding modes between 3g and the active site of Ca-FBA-II have been proposed by using the DOX (docking, ONIOM, and XO) strategy. To our knowledge, no FBA-II inhibitors with antifungal activities against wild type and resistant strains from Candida were reported previously. The positive results suggest that the strategy adopted in this study are a promising method for the discovery of novel drugs against azole-resistant fungal pathogens in the future.
Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: Design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties
Singh, Udaya Pratap,Bhat, Hans Raj,Verma, Amita,Kumawat, Mukesh Kumar,Kaur, Rajinder,Gupta,Singh, Ramendra K.
, p. 17335 - 17348 (2013/09/24)
A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.
Synthesis, characterization and antibacterial screening of new pyrazole and pyrazoline-5-one derivatives
Nagaraju,Srinivasulu,Doraswamy,Venkata Ramana
experimental part, p. 293 - 298 (2012/03/11)
A series of N′-(p-toluene sulphonyl)-3-methyl-4-(substituted arylhydrazono)-2-pyrazoline-5-ones and N′-(2-hydroxybenzoyl)-3,5-dimethyl- 4-(substituted arylazo)pyrazoles have been synthesized and characterized by chemical analysis, IR and 1H NMR spectral data. The compounds have been screened for antibacterial activity against Staphylococcus aureus and Escherichia coli.
Reactions of copper(II) β-diketonates under free radical conditions. II. Diazonium salts as aryl radicals source in the arylation of β-diketones
Lorris, Maria E.,Abramovitch, Rudolph A.,Marquet, Jorge,Moreno-Manas, Marcial
, p. 6909 - 6916 (2007/10/02)
Copper complexes of 2,2,6,6-tetramethylheptane-3,5-dione and other β-diketones afford α-aryl-β-diketones when treated with arenediazonium tetrafluoroborates and copper powder in dichloromethane.
