74-39-5Relevant articles and documents
Azo-dyes based small bifunctional molecules for metal chelation and controlling amyloid formation
Rana, Monika,Cho, Hong-Jun,Roy, Tapta Kanchan,Mirica, Liviu M.,Sharma, Anuj K.
, p. 419 - 429 (2018)
Chemical tools are needed to discover new effective drugs for tackling multifaceted complex neurodegenerative diseases like Alzheimer's disease (AD). Multifunctional nature of two compounds, 5-((4-nitrophenyl)diazenyl)quinolin-8-ol (HL1) and 4-((4-nitrophenyl)diazenyl)benzene-1,3-diol (HL2) is reported w.r.t. their ability to bind Cu2+ ions and amyloid aggregates related to AD. HL1 and HL2 have half congo-red type azo-stilbene structural framework incorporated with metal chelating groups, designed to chelate metal ions from metal-amyloid species. Metal binding studies of HL1 and HL2 are established by the methods of Job's Plot, UV-vis spectra with metal ions and stability constant determination. In addition, their metal complexes are isolated, purity checked by elemental analysis, spectroscopically characterized and their structural analyses were obtained from DFT based calculations including binding energy determination. Chicken egg white Lysozyme (CEWL) was used as a model peptide for fibrillation studies. HL1 is found as an excellent colorimetric sensor for amyloid fibrils. Inhibitory effect of HL1 and HL2 and their isolated metal complexes L1-Cu and L2-Cu on CEWL fibrillation was studied using ThT and ANS fluorescence assay along with TEM imaging. In addition, the cell toxicity studies on these compounds suggest that although azo dyes may be non-toxic but having a nitro-substitution lead to significant cell toxicity. Overall, these results suggest that this new class of multifunctional small molecules can interact with amyloids as well as metal ions and could be potential anti-aggregation metal chelating agents.
New generation of nitrite functionalized star-like polyvinyl imidazolium compound: Application as a nitrosonium source and three dimensional nanocatalyst for the synthesis of azo dyes
Shomali, Ashkan,Valizadeh, Hassan,Noorshargh, Saeideh
, p. 409 - 418 (2017/07/24)
The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.
Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
Valizadeh, Hassan,Shomali, Ashkan,Ghorbani, Jalal,Noorshargh, Saeideh
, p. 64 - 71 (2015/03/04)
Nitrite functionalized star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional nitrosonium source and catalyst because of its poly ionic characteristic. The isolated products were confirmed with FT-IR spectrum, 1H-NMR, 13C-NMR spectroscopy and CHNSO analysis. The structure of heterogeneous reagent and catalyst was confirmed by FT-IR spectrum, SEM images, EDX and CHNSO analysis. Yields and reaction times for the synthesis of a variety of products via this procedure were compared with reported values in literature.
