123953-16-2Relevant academic research and scientific papers
New antibacterial agents: Hybrid bioisoster derivatives as potential E. coli FabH inhibitors
Segretti, Natanael D.,Serafim, Ricardo A.M.,Segretti, Mariana C.F.,Miyata, Marcelo,Coelho, Fernando R.,Augusto, Ohara,Ferreira, Elizabeth I.
, p. 3988 - 3993 (2016)
The development of resistance to antibiotics by microorganisms is a major problem for the treatment of bacterial infections worldwide, and therefore, it is imperative to study new scaffolds that are potentially useful in the development of new antibiotics
Electrochemical characterization of para- and meta-nitro substituents in aqueous media of new antichagasic pharmaceutical leaders
Sanz, Caroline G.,Dias, Kevin A.,Bacil, Raphael P.,Serafim, Ricardo A.M.,Andrade, Leandro H.,Ferreira, Elizabeth I.,Serrano, Silvia H.P.
, (2021)
The electrochemical reduction mechanism of two isomers of position drug leaders against Chagas disease, p-nitrosulfonylhydrazine derivative (p-NSF), and m-nitrosulfonylhydrazine derivative (m-NSF), was investigated in aqueous media and in the absence of oxygen using voltammetric techniques. The main reduction process was attributed to the reduction of the nitro group (Epc (p-NSF) = ?0.58 V and Epc (m-NSF) = ?0.62 V), generating nitroso derivative in intermediate and higher values of pH and hydroxylamine in lower values of pH. Another reduction process in a less negative potential value was only observed for p-NSF and attributed to the generation of the nitro radical anion. The difference in the reduction potentials between both compounds and the presence of another reduction process for p-NSF was associated with the position of the nitro group, due to the distinct stabilization of the reduction intermediates by the aromatic ring. A catalytic response for the reduction process of the nitro anion radical was observed for p-NSF in the presence of oxygen, given that its magnitude of current increased when increasing the oxygen availability. Also, for m-NSF, this reduction process could be detected, even though it was not observed in the voltammograms in the absence of oxygen. This further confirmed the generation of the nitro radical anion, since it reacts with molecular oxygen and regenerates the initial nitro compound. The interaction with cysteine was also evaluated, which favored the reduction process towards the generation of the nitroso derivative due to adduct formation, destabilizing the reduction process regarding the nitro radical anion. Therefore, electrochemical experiments can evaluate how different isomers of position and other coupled functional groups affect the reduction of the nitro group and, consequently aid in the design of new classes of antichagasic pharmaceuticals, with improved stability of reactive intermediates that are often correlated with the degree of injury towards the parasite.
Synthesis and characterization of a new family of energetic salts based on guanidinium cation containing furoxanyl functionality
Wu, Bo,Wang, Zhixin,Yang, Hongwei,Lin, Qiuhan,Ju, Xuehai,Lu, Chunxu,Cheng, Guangbin
, p. 58243 - 58251 (2014)
A new family of energetic salts based on a new guanidinium cation containing furoxanyl functionality, 1-(3′-methylfuroxanyl)methyleneamino guanidinium cation, were synthesized and well characterized by IR and multinuclear NMR spectroscopy, elemental analysis as well as differential scanning calorimetry. The structures of salts 1, 4, 5 and 6 were confirmed by single-crystal X-ray diffraction. Most of the salts decompose at temperatures over 180 °C. Furthermore, except for salts 7 and 9, the remaining energetic salts exhibit low impact sensitivities (15-40 J), friction sensitivities (120-360 N), and are insensitive to electrostatics. The detonation pressure values calculated for these salts range from 19.3 to 27.5 GPa, and the detonation velocities range from 7515 to 8402 m s-1. These results make some energetic salts potential candidates for energetic materials with good thermal stabilities and low sensitivities. This journal is
Combining the furoxanylhydrazone framework with various energetic functionalities to prepare new insensitive energetic materials with 3D-cube layer stacking
Tang, Jie,Yang, Hongwei,Xiong, Hualin,Hu, Wei,Lei, Caijin,Cheng, Guangbin
, p. 5895 - 5902 (2020)
A series of furoxanylhydrazone-derived energetic compounds including salts and neutral compounds were systematically studied using 3-methyl-4-furoxancarbaldehyde as a versatile starting material. Target compounds present a 3D-cube layer crystal packing style due to the special structure of furoxanylhydrazone and vast hydrogen bonds. This configuration breaks through the limitation of the 2D-plane layer structure. Target compounds, which feature such characteristics, exhibit excellent sensitivities toward impact and friction (IS > 24 J; FS > 180 N) and acceptable energetic performance. Moreover, the detonation velocities and pressures of all ionic compounds (6-9, 11-13) were both increased relative to their corresponding neutral compounds. Compared with 5-(3′-methylfuroxanyl)methyleneamino-tetrazole (10), the sensitivities to impact and friction of its anion salts (11-13) were also lowered to some extent. The structure-property relationship was studied using theoretical calculations, crystal structure analysis and energetic properties. It is noted that five types of crystal packing have been analyzed, which may be useful for the further understanding of crystal and chemical phenomena in energetic materials. The results obtained demonstrate that this study enriches future prospects for the design of energetic materials.
Synthesis and preliminary evaluation of N-oxide derivatives for the prevention of atherothrombotic events
Rosseto, Leandro Augusto,Pires, Maria Elisa Lopes,Melchior, Aylime Castanho Bolognesi,Bosquesi, Priscila Longhin,Pavan, Aline Renata,Marcondes, Sisi,Chung, Man Chin,Dos Santos, Jean Leandro
, p. 18185 - 18200 (2015)
Thrombosis is the main outcome of many cardiovascular diseases. Current treatments to prevent thrombotic events involve the long-term use of antiplatelet drugs. However, this therapy has several limitations, thereby justifying the development of new drugs
Synthesis and biological evaluation of novel hybrid chalcone derivatives as vasorelaxant agents
Dong, Xiaowu,Du, Lilin,Pan, Zhichao,Liu, Tao,Yang, Bo,Hu, Yongzhou
, p. 3986 - 3992 (2010)
With the aim to further improve the vasorelaxant activities of chalcones, nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donor or 1,4-dihydropyridyl (1,4-DHP) moiety were designed and synthesized based on molecular hybridization strategy. Their vasorelaxant activities were evaluated in aortic rings with endothelium pre-contracted with phenylephrine (PE). All of these compounds showed preferable vasorelaxant activities which were more potent than their parent compounds. Compounds 8c and 15c, the most potent compounds, would be promising structural templates for the development of novel vasorelaxant agents. Nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donors or 1,4-dihydropyridyl moiety were designed, synthesized and biological evaluated for their vasorelaxant activities.
In Vitro Metabolic Stability and in Vivo Biodistribution of 3-Methyl-4-furoxancarbaldehyde Using PET Imaging in Rats
Pippin, Adam B.,Mohd Arshad, Zaira Hidayah,Voll, Ronald J.,Nye, Jonathon A.,Ghassabian, Sussan,Williams, Craig M.,Mancini, Alessandra,Liotta, Dennis C.,Smith, Maree T.,Goodman, Mark M.
, p. 563 - 567 (2016)
Painful diabetic neuropathy (PDN) is a type of peripheral neuropathic pain that is currently difficult to treat using clinically available analgesics. Recent work suggests a progressive depletion of nitric oxide (NO) in nerve cells may be responsible for the pathobiology of PDN. The nitric oxide donor, 3-methyl-4-furoxancarbaldehyde (PRG150), has been shown to produce dose-dependent analgesia in a rat model of PDN. To gain insight into the mechanism of analgesia, methods to radiolabel PRG150 were developed to assess the in vivo biodistribution in rats. The furoxan ring was labeled with 13N to follow any nitric oxide release and the 3-methyl substituent was labeled with 11C to track the metabolite using PET imaging. The in vitro metabolic stability of PRG150 was assessed in rat liver microsomes and compared to in vivo metabolism of the synthesized radiotracers. PET images revealed a higher uptake of 13N over 11C radioactivity in the spinal cord. The differences in radioactive uptake could indicate that a NO release in the spinal cord and other components of the somatosensory nervous system may be responsible for the analgesic effects of PRG150 seen in the rat model of PDN.
4-(1-Amino-5-aminotetrazolyl)methyleneimino-3-methylfuroxan and its derivatives: Synthesis, characterization, and energetic properties
Tang, Yongxing,Yang, Hongwei,Shen, Jianhua,Wu, Bo,Ju, Xuehai,Lu, Chunxu,Cheng, Guangbin
, p. 1231 - 1238 (2014)
The condensation reaction of 4-formyl-3-methylfuroxan with 1,5-diaminotetrazole led to 4-(1-amino-5-aminotetrazolyl)methyleneimino-3- methylfuroxan (1) in high yield. Its structure was confirmed by an X-ray diffraction study. 4-(1-Amino-5-nitriminotetrazolyl)methyleneimino-3- methylfuroxan (2) was obtained through the nitration of 1 with 100 % HNO 3. The nitrogen-rich salts of 2 with bases such as 1-amino-1,2,3-triazole (3), 4-amino-1,2,4-triazole (4), and 3-amino-1,2,4- triazole (5) were synthesized and characterized by IR, Raman, and NMR spectroscopy and elemental analysis. In addition, the structures of 2, 4, and 5 were further confirmed by single-crystal X-ray diffraction analyses. Compound 5 decomposes at 183 °C, whereas 3 and 4 are less stable and decompose at 139 and 164 °C, respectively. The heats of formation, detonation parameters, and impact sensitivity of 1-5 were investigated by theoretical and experimental methods. The synthesis of 4-(1-amino-5-aminotetrazolyl)methyleneimino-3- methylfuroxan from 3-methyl-4-formylfuroxan and 1,5-diaminotetrazole yields a thermally stable energetic compound. Its nitroiminotetrazole derivative exhibits high positive heats of formation and good detonation performance. Three nitrogen-rich energetic salts combine moderate thermal stabilities with acceptable sensitivities. Copyright
Schiff bases containing a furoxan moiety as potential nitric oxide donors in plant tissues
Georgescu, Emilian,Oancea, Anca,Georgescu, Florentina,Nicolescu, Alina,Oprita, Elena Iulia,Vladulescu, Lucian,Vladulescu, Marius-Constantin,Oancea, Florin,Shova, Sergiu,Deleanu, Calin
, (2018)
Stable Schiff bases containing a furoxan moiety are synthesized as single regioisomers by the reaction of 3-methyl-2-oxy-furazan-4-carbaldehydewith various amino compounds at room temperature. The structures of synthesized compounds were fully characterized by multinuclear NMR spectroscopy and X-ray crystallography. The effect of synthesized Schiff bases containing a furoxan moiety on biological generation of reactive oxygen species and nitric oxide in plant tissues was investigated for the first time by fluorescence microscopy and the released NO identified as nitrite with Griess reagent. There is a good correlation between the biological generation of NO determined by fluorescence microscopy and with Griess reagent. Some of the synthesized compounds exhibited both nitric oxide and reactive oxygen species generation abilities and represent potential NO donors in plant tissues.
Synthesis and biological evaluation of some new furoxan derivatives as anti-inflammatory agents
Amir, Mohd,Verma, Jeevan S.,Tariq, Sana,Somakala,Ehtaishamul Haq
, p. 955 - 959 (2019/05/21)
A new series of furoxan derivatives (3a-k) have been synthesized and characterized by their IR, 1H NMR and mass spectral data. All the compounds have been screened for their anti-inflammatory activity. The compounds 3a, 3b, 3f, 3g, and 3i which show significant anti-inflammatory activity have been further studied for their ulcerogenic activities and nitric oxide releasing properties. Furoxan derivative 3-memyl-4-[{2-(2-phenylacetyl)hydrazono}memyl]-furoxan 3f showed greater anti-inflammatory activity comparable to standard drug ibuprofen. The compound also showed reduced, ulcerogenicity and high nitric oxide releasing properties.
