- Revisiting the thermal decomposition of five ortho-substituted phenyl azides by calorimetric techniques
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The thermal decomposition (TD) of 2-azidophenylmethanol (1), 2-azidobenzenecarbaldehyde (2), 1-(2-azidophenyl)-1-ethanone (3), (2-azidophenyl)(phenyl)methanone (4) and 1-azido-2-nitrobenzene (5) was analysed by DSC, TG and C80 calorimetric techniques under both oxidative and non-oxidative conditions. The TD of these azides in solution is well known to give the corresponding benzoxazoles, generally in good yields, with the exception of azide 1. When both the outcomes from the solid phase and in 'solution phase' TD reactions combined with the results from EI-MS experiments were considered, sufficient information was available to estimate the azides intrinsic molecular reactivity (MIR).
- Cardillo, Paolo,Gigante, Lucia,Lunghi, Angelo,Zanirato, Paolo
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- Design, synthesis and antifungal activity of novel indole derivatives linked with the 1,2,3-triazole moiety via the CuAAC click reaction
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A series of novel indole derivatives linked with the 1,2,3-triazole moiety was designed, synthesised by the CuCl2/Zn-catalysed Huisgen cycloaddition and characterised. The antifungal activity of all the prepared compounds against Colletotrichum capsici and cotton Physalospora pathogens was evaluated and the results indicated that these compounds showed inhibitory effect for fungi and the inhibition ratio of the best was up to 83.3%. The preliminary structure-activity relationship is also discussed in this paper.
- Xu, Guiqing,Zhao, Jinglin,Jiang, Yuqin,Zhang, Peng,Li, Wei
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- Synthesis and antimicrobial potential of nitrofuran-triazole congeners
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A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive and Gram-ne
- Kamal, Ahmed,Hussaini, S. M. Ali,Sucharitha, M. Lakshmi,Poornachandra,Sultana, Faria,Ganesh Kumar
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- Synthesis of aryl azides via post-cleavage modification of polymer-bound triazenes
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Starting from immobilized arenes on the triazene T1 linker resin, cleavage was achieved by trifluoroacetic acid in the presence of trimethylsilyl azide to obtain aryl azides in good yields and excellent purities. A novel cleavage protocol has been introduced and analytical and preparative applications have been presented.
- Avemaria, Frank,Zimmermann, Viktor,Br?se, Stefan
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- Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX
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Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC50 = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.
- Abid, Mohammad,Alajmi, Mohamed F.,Aneja, Babita,Daniliuc, Constantin G.,Hasan, Phool,Hassan, Md. Imtaiyaz,Hussain, Afzal,Khan, Parvez,Mohsin, Mohd.,Queen, Aarfa,Rizvi, M. Moshahid A.,Shamsi, Farheen
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- Synthesis and discovery of asiatic acid based 1,2,3-triazole derivatives as antitumor agents blocking NF-κB activation and cell migration
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A series of asiatic acid (AA) based 1,2,3-triazole derivatives were designed, synthesized and subjected to a cell-based NF-κB inhibition screening assay. Among the tested compounds, compound 6k displayed impressive NF-κB inhibitory activity with an ICsub
- Huang, Ri-Zhen,Liang, Gui-Bin,Li, Mei-Shan,Fang, Yi-Lin,Zhao, Shi-Feng,Zhou, Mei-Mei,Liao, Zhi-Xin,Sun, Jing,Wang, Heng-Shan
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- Synthesis, characterization, and pharmacological studies of ferrocene-1H-1,2,3-triazole hybrids
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A series of ferrocene-1H-1,2,3-triazole hybrids namely 1-(4-nitrophenyl)-4-ferrocenyl-1H-1,2,3-triazole (1), 1-(4,4′-dinitro-2-biphenyl)-4-ferrocenyl-1H-1,2,3-triazole (2), 1-(3-chloro-4-fluorophenyl)-4-ferrocenyl-1H-1,2,3-triazole (3), 1-(4-bromophenyl)-
- Haque, Ashanul,Hsieh, Ming-Fa,Hassan, Syed Imran,Haque Faizi, Md. Serajul,Saha, Anannya,Dege, Necmi,Rather, Jahangir Ahmad,Khan, Muhammad S.
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- Benzooxadiazaole-based D-A-D co-oligomers: Synthesis and electropolymerization
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Four D-A-D type co-oligomers have been synthesized by Stille condensation between monostannyl derivatives of furan/thiophene/selenophene/3,4- ethylenedioxythiophene (EDOT) and 4,7-dibromo-benzo[1,2,5]oxadiazole. All these co-oligomers were successfully electrochemically polymerized in dichloromethane and characterized by spectroelectrochemistry. All four polymers possess narrow optical band gap. Spectroelectrochemical studies of polymer films on indium tin oxide revealed that the replacement of donor EDOT with furan/thiophene/ selenophene has affected the low-energy charge-carrier (bipolaron) formation significantly. Kinetic studies based on chronoamperometry show that the polymer P5 (EDOT-capped benzo[1,2,5]oxadiazole system) possess better electrochromic property with high transmittance (66%) in visible region than the other copolymers.
- Pati, Palas Baran,Das, Soumyajit,Zade, Sanjio S.
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- Synthesis, characterization and thermal behavior study of new 1,2,3-triazole derivatives containing 1,3,4-oxadiazole ring
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In this present work, a series of new 1-(substituted-phenyl)-1H-1,2,3-triazolyl-4-carboxylic acid derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction. Since these synthesized 1,2,3-triazole compounds containing a carbo
- Nahi, Riyadh J.,Kuwait, Zainab I.
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- Cellulose sulphuric acid as a biodegradable catalyst for conversion of aryl amines into azides at room temperature under mild conditions
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This article describes simple and efficient method for the diazotization and azidation of different aromatic amines over cellulose sulphuric acid, sodium nitrite and sodium azide under mild conditions at room temperature. Various aryl amines possessing electron-withdrawing groups or electron-donating groups have been converted into the corresponding aryl azides with 71-99% yields. The use of mild reaction conditions, avoids the use of harmful acids and toxic solvents and short reaction times are advantages of this methodology. The selected catalyst is found to be highly efficient and recyclable.
- Nemati, Firouzeh,Elhampour, Ali
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- 1,2,3-Triazole-quinazolin-4(3H)-one conjugates: evolution of ergosterol inhibitor as anticandidal agent
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The present study describes the synthesis of 1,2,3-triazole-quinazolinone conjugates (5a-q) from ethyl 4-oxo-3-(prop-2-ynyl)-3,4-dihydroquinazoline-2-carboxylate and phenyl azide/substituted phenyl azides employing Cu(i) catalysed Huisgen 1,3-dipolar cycloaddition. The corresponding acids (6a-q) were obtained by hydrolysis of esters (5a-q) to study the effect of these functionalities on the biological activity. All synthesized compounds were screened for in vitro anticandidal evaluation against Candia albicans, Candida glabrata and Candida tropicalis strains. The results indicated that compound 5n showed potent anticandidal activity with IC50 in the range of 8.4 to 14.6 μg mL?1. Hemolytic activity using human red blood cells (hRBCs) and cytotoxicity by MTT assay on human embryonic kidney (HEK-293) cells revealed the non-toxic nature of the selected compounds. Growth kinetic study with compound 5n showed its fungicidal nature as no significant growth of Candida cells was observed even after 24 h. Cellular ergosterol content was determined in the presence of different concentrations of 5n to measure the activity of lanosterol 14α-demethylase indirectly. The results showed significant disruption of the ergosterol biosynthetic pathway through inhibition of lanosterol 14α-demethylase activity supported by docking studies (PDB: 5v5z). Overall, this study demonstrates the anticandidal potential of 5n which can serve as the lead for further structural optimization and SAR studies.
- Masood, Mir Mohammad,Irfan, Mohammad,Khan, Parvez,Alajmi, Mohamed F.,Hussain, Afzal,Garrison, Jered,Rehman, Md. Tabish,Abid, Mohammad
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- Biofilm inhibition and DNA binding studies of isoxazole-triazole conjugates in the development of effective anti-bacterial agents
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Isoxazole-triazole conjugates (8a-q) were synthesized using click chemistry approach and their biological activities were explored to develop novel antibacterial agents. In vitro antibacterial screening against Gram-positive as well as Gram-negative bacterial strains identified compounds 8b and 8m with potent inhibitory potential against selective bacterial cells. 8b showed IC50 value of 67.6 μg/mL against P. aeruginosa while 8m exhibited better activity against Gram-positive bacteria S. pneumoniae and E. faecalis having IC50 values 74.13 and 44.7 μg/mL, respectively. Effect on growth kinetics of the bacterial cells as well as cytotoxicity studies on human embryonic kidney cells (HEK293) further supports their biological potential. Compound 8m significantly inhibited biofilm formation of E. coli cells visualized by scanning electron microscopy (SEM) analysis. The interaction of these compounds with ctDNA, as their possible mode of action, was studied using multi-spectroscopic techniques and molecular docking. The data suggested that compound 8m intercalate in the minor groove of DNA.
- Habib, Farhat,Alam, Shadab,Hussain, Afzal,Aneja, Babita,Irfan, Mohammad,Alajmi, Mohamed F.,Hasan, Phool,Khan, Parvez,Rehman, Md Tabish,Noman, Omar Mohammed,Azam, Amir,Abid, Mohammad
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- Ionic liquids/[bmim][N3] mixtures: Promising media for the synthesis of aryl azides by SNAr
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(Formula Presented) The nucleophilic aromatic substitution of some activated aryl or heteroaryl halides has been performed in ionic liquid solution, using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction course was studied varying the
- D'Anna, Francesca,Marullo, Salvatore,Noto, Renato
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- Molecular docking studies on COVID-19 and antibacterial evaluation of newly synthesized 4-(methoxymethyl)-1,2,3-triazolean analogues derived from (E)-1-phenyl-3-(2-(piperidin-1-yl)quinolin-3-yl) prop-2-en-1-one
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A series of novel quinolone-based 4-(methoxymethyl)-1,2,3-triazole derivatives were synthesized, and their structures were characterized by 1H, 13C NMR and mass spectroscopy. The compounds (IXa-l) were screened in vitro antibacterial
- Jalapathi, P.,Nagamani, M.,Srinivas, M.,Vishnu, T.
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- A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation
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A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc
- Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng
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- Design, Synthesis and Evaluation of a Series of 1,5-Diaryl-1,2,3-triazole-4-carbohydrazones as Inhibitors of the YAP-TAZ/TEAD Complex
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Starting from our previously reported hit, a series of 1,5-diaryl-1,2,3-triazole-4-carbohydrazones were synthesized and evaluated as inhibitors of the YAP/TAZ-TEAD complex. Their binding to hTEAD2 was confirmed by nanodifferential scanning fluorimetry, an
- Gibault, Floriane,Sturbaut, Manon,Coevoet, Mathilde,Pugnière, Martine,Burtscher, Ashley,Allemand, Frédéric,Melnyk, Patricia,Hong, Wanjin,Rubin, Brian P.,Pobbati, Ajaybabu V.,Guichou, Jean-Fran?ois,Cotelle, Philippe,Bailly, Fabrice
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p. 2823 - 2844
(2021/07/10)
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- Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids
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Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].
- Awolade, Paul,Cele, Nosipho,Kerru, Nagaraju,Singh, Parvesh
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p. 2201 - 2218
(2020/06/17)
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- Synthesis and Molecular Docking of novel 1,3-Thiazole Derived 1,2,3-Triazoles and In vivo Biological Evaluation for their Anti anxiety and Anti inflammatory Activity
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Heterocyclic rings such as thiazole and triazole are considered as privileged moieties, since they constitute several drugs for biological treatment. In this work, a novel series of 1, 3-thiazole linked 1,2,3-triazole derivatives were designed and synthesized according to convenient synthetic procedures. All the synthesized compounds are characterized by 1H NMR, 13C NMR and LCMS techniques. The molecular docking was studied to illustrate the binding interactions of target molecules with GABAA receptor. The synthesized compounds containing 1,3-thiazole and 1,2,3-triazole ring, the presence of these rings in each molecule may lead to have potential in vivo anti-anxiety and anti-inflammatory properties. The in vivo activity result revealed that some of the compounds possessed statistical significant therapeutic efficacy. Anti-anxiety screening on mice indicated that all the target compounds (5mg/kg) exhibited certain extent of an anxiolytic effect by increasing time spent on open arms and the percentage of open arm entries as compared to controlled group. More importantly, among the newly synthesized compounds (6h) and (6i) have strong anti-anxiety against mice. The non steroidal anti-inflammatory activity drugs (NSAIDs) are plays a very important role to prevent the growth of cyclooxygenase enzymes which are responsible for inflammation and pain. The results show that the following compounds 6e, 6g, 6h, and 6k are having maximum anti inflammatory activity against carrageenan induced acute inflammation in rats comparable to diclofenac as reference drug. Molecular docking simulations were employed to find out the important binding modes responsible for the anti anxiety activity, thus supporting their effective anti-anxiety efficacy.
- Ankali, Kariyappa N,Rangaswamy, Javarappa,Shalavadi, Mallappa,Naik, Nagaraja,Krishnamurthy, Ganga naik
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- Synthesis, Characterization, and Cytotoxic Evaluation of New Triazole Derivatives of Osthol
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Abstract: Osthol [7-methoxy-8-(3-methylbut-2-en-1-yl)chromen-2-one] isolated fromPrangos pabularia was used as a startingmaterial for the synthesis of its various derivatives via modifications of thelactone ring. The resulting compounds were fully charact
- Banday, J. A.,Chisti, H. N.,Rather, Z. K.
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p. 986 - 993
(2021/07/22)
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- Synthesis and In Vitro Anticancer Activity of Triazolyl Analogs of Podophyllotoxin, a Naturally Occurring Lignin
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Abstract: A series of triazolyl-modified podophyllotoxin analogs have been designed and synthesized by utilizing Huisgen 1,3-dipolar cycloaddition in order to develop potent antitumor agents. The synthesized analogs were assessed for in vitro anticancer a
- Ara, T.,Banday, J. A.,Bhat, B. A.,Ganaie, B. A.
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p. 2039 - 2047
(2022/01/24)
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- Synthesis of nitrophenyl and fluorophenyl azides and diazides by SNAr under phase-transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents
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Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a SNAr substitution on halogenated benzenes with a phase-transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron-withdrawing substituents (COH, COR, COOR, CN, NO2, or F). A discussion on the mechanisms and the products obtained in these SNAr reactions is presented.
- Leyva, Elisa,Aguilar, Johana,González-Balderas, Regina M.,Vega-Rodríguez, Sarai,Loredo-Carrillo, Silvia E.
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- Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
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The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.
- Goljani, Hamed,Tavakkoli, Zahra,Sadatnabi, Ali,Nematollahi, Davood
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supporting information
p. 5920 - 5924
(2020/08/12)
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- A Metal-Free Synthesis of N-Aryl Oxazolidin-2-Ones by the One-Pot Reaction of Carbon Dioxide with N-Aryl Aziridines
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The cost-effective TPPH2/TBACl-catalyzed (TPPH2=dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N-aryl aziridines was successful in synthesizing N-aryl oxazolidin-2-ones. A cataly
- Sonzini, Paolo,Damiano, Caterina,Intrieri, Daniela,Manca, Gabriele,Gallo, Emma
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supporting information
p. 2961 - 2969
(2020/07/06)
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- Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents
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A series of thirty one novel 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-3-methylquinoxaline-1,4-dioxide (7a-l), 3-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6-chloro-2-methylquinoxaline-1,4-dioxide (8a-l) and 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6,7-dichloro-3-methylquinoxaline-1,4-dioxide (9a-g) analogues were synthesized, characterized using various analytical techniques and single crystal was developed for the compounds 8 g and 9f. Synthesized compounds were evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain and two clinical isolates Spec. 210 and Spec. 192. The titled compounds exhibited minimum inhibitory concentration (MIC) ranging from 30.35 to 252.00 μM. Among the tested compounds, 8e, 8 l, 9c and 9d exhibited moderate activity (MIC = 47.6 – 52.0 μM) and 8a exhibited significant anti-tubercular activity (MIC = 30.35 μM). Furthermore, 8e, 8 l, and 9d were found to be less toxic against human embryonic kidney, HEK 293 cell lines. Finally, a docking study was also performed using MTB DNA Gyrase (PDB ID: 5BS8) for the significantly active compound 8a to know the exact binding pattern within the active site of the target enzyme.
- Aggarwal, Himanshu,Ewa, Augustynowicz-Kopec,G?ogowska, Agnieszka,Ghosh, Balaram,Kumar, Banoth Karan,Murugesan, Sankaranarayanan,Nandikolla, Adinarayana,Pulya, Sravani,Sekhar, Kondapalli Venkata Gowri Chandra,Srinivasarao, Singireddi,Suresh, Amaroju
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supporting information
(2020/05/29)
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- Identification and structure–activity relationship (SAR) studies of carvacrol derivatives as potential anti-malarial against Plasmodium falciparum falcipain-2 protease
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In an effort to develop a potent anti-malarial agent against Plasmodium falciparum, a structure-guided virtual screening using an in-house library comprising 652 compounds was performed. By docking studies, we identified two compounds (JMI-105 and JMI-346
- Uddin, Amad,Singh, Vigyasa,Irfan, Iram,Mohammad, Taj,Singh Hada, Rahul,Imtaiyaz Hassan, Md,Abid, Mohammad,Singh, Shailja
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- Synthesis and antitumor activity of α,β-unsaturated carbonyl moiety- containing oleanolic acid derivatives targeting PI3K/AKT/mTOR signaling pathway
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Oleanolic acid (OA) and its semi-synthetic derivatives have been reported to have a wide range of biological activities. The introduction of electrophilic Michael acceptor group can increase the reactivity of OA to cellular targets and thus improve the an
- Wang, Shi-Sheng,Zhang, Qiao-Li,Chu, Peng,Kong, Ling-Qi,Li, Guang-Zhe,Li, Yue-Qing,Yang, Li,Zhao, Wei-Jie,Guo, Xiu-Han,Tang, Ze-Yao
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- Chan-Lam-type Azidation and One-Pot CuAAC under CuI-Zeolite Catalysis
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The copper(I)-exchanged zeolite CuI-USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy-to-prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional-group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one-pot CuI-catalyzed process.
- Clerc, Arnaud,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
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p. 2060 - 2065
(2020/03/03)
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- Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides
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We report a series of efficient procedures to prepare 2-nitrophenyl-4-aryl-1,2,3-triazoles avoiding the isolation of potentially hazardous 2-nitrophenyl azides. An organocatalyzed azide-enolate variant allows efficient access to the target compounds while
- Cisnetti, Federico,Roux, Amélie
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p. 610 - 614
(2020/03/27)
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- Iron and Ruthenium Glycoporphyrins: Active Catalysts for the Synthesis of Cyclopropanes and Aziridines
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In view of the relevance of cyclopropanes and aziridines as synthetic building blocks as well as active parts in biological and pharmaceutical compounds, the development of sustainable synthetic procedures for obtaining these products continues to be a si
- Damiano, Caterina,Gadolini, Sebastiano,Intrieri, Daniela,Lay, Luigi,Colombo, Cinzia,Gallo, Emma
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supporting information
p. 4412 - 4420
(2019/11/03)
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- Synthesis and Biological Evaluation of New Ibuprofen-1,3,4-oxadiazole-1,2,3-triazole Hybrids
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A new hybrid polydentate template comprising distinctive pharmacophoric groups, namely, ibuprofen, 1,3,4-oxadiazole, and 1,2,3-triazole linked through a thioether bridge was achieved by one-pot synthesis by exploring multicomponent Cu-catalyzed “click chemistry” approach. The target structures were characterized by NMR, IR, and LC-Mass. The X-ray analysis of 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8a) confirmed the assigned structure. The in vitro antibacterial and anticancer activity of these compounds revealed that 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8b) demonstrated more potent antibacterial activity against Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa) and 2-(((1-(2,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-5-(1-(4 isobutylphenyl)ethyl)-1,3,4-oxadiazole (8e) exhibited anticancer activity with IC50 of 27.50 and 31.03?μg/mL against HeLa and MCF-7 cell lines, respectively.
- Rayam, Parsharamulu,Polkam, Naveen,Kummari, Bhaskar,Banothu, Venkanna,Gandamalla, Durgaiah,Yellu, Narsimha Reddy,Anireddy, Jaya Shree
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p. 296 - 305
(2018/12/13)
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- Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
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Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
- Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
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p. 665 - 674
(2018/09/14)
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- Unveiling novel diphenyl-1H-pyrazole based acrylates tethered to 1,2,3-triazole as promising apoptosis inducing cytotoxic and anti-inflammatory agents
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Meagre and suboptimal therapeutic response along with the side effect profile associated with the existing anticancer therapy have necessitated the development of new therapeutic modalities to curb this disease. Bearing in mind the current scenario, a series of 1,2,3-triazole linked 3-(1,3-diphenyl-1H-pyrazol-4-yl)acrylates was synthesized following a multi-step reaction scheme. Initial screening for anticancer potential was done by in vitro sulforhodamine B assay against four human cancer cell lines- MCF-7 (breast), A549 (Lung) and HCT-116 and HT-29 (Colon). On evaluation, several compounds showed promising growth inhibition against all the cell lines, particularly compounds 6e, 6f and 6n. Among them, compound 6f displayed IC50 values of 1.962, 3.597, 1.764 and 4.496 μM against A549, HCT-116, MCF-7 and HT-29 cell lines respectively. Furthermore, the apoptosis inducing potential of the compounds was determined by Hoechst staining and DNA fragmentation assay. Colony formation inhibition assay was also carried out to determine the long term cytotoxic potential of the molecules. Moreover, compounds 6e, 6f and 6n were also evaluated for anti-inflammatory activity by protein albumin denaturation assay and red blood cell membrane stabilizing assay.
- Khan, Mohemmed Faraz,Anwer, Tarique,Bakht, Afroz,Verma, Garima,Akhtar, Wasim,Alam, M. Mumtaz,Rizvi, Moshahid Alam,Akhter, Mymoona,Shaquiquzzaman, Mohammad
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p. 667 - 678
(2019/04/05)
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- Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model
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In the present study a library of thiophenol-formaldehyde-triazole (TFT) derivatives was synthesized and screened against CAOV3, CAOV4 and ES-2 ovary cancer cell lines. Initial screening revealed that five-compounds 5a, 5b, 5j, 5h and 5i inhibited the viability of tested cell lines. Analysis of apoptosis revealed that increase in compound 5a (most active) concentration from 0.25 to 2.0 μM enhanced apoptotic cell proportion. Transwell assay showed reduction in invasive potential of CAOV3 cells on treatment with compound 5a. In wound healing assay increasing the concentration of compound 5a from 0.5 to 2.0 μM caused a significant (P 0.05) decrease in the migration potential. Western blotting showed that compound 5a treatment markedly decreased the level of matrix metalloproteinase (MMP)-2 and ?9 in CAOV3 cells. Treatment of CAOV3 cells with compound 5a caused a marked decrease in Focal Adhesion Kinase (FAK) activation. Tumor growth was inhibited in the compound 5a treated mice markedly than those of untreated group. The tumor metastasis to liver, intestine, spleen and peritoneal cavity was markedly decreased in mice treated with 10 mg/kg dose of compound 5a. Examination of Von Willebrand factor (vWF) expression in liver, intestinal and pulmonary lesions showed a marked decrease in the compound 5a-treated mice. The infiltration of macrophages in the metastatic lesions showed a significant decrease in compound 5a-treated mice. In conclusion, the compound 5a inhibited ovary cancer cell viability and induced apoptosis through decrease in expression of vWF and metalloproteinase, suppression of FAK activation and decrease in infiltration of macrophages. The compound 5a therefore can be investigated further for the treatment of ovary cancer.
- Jia, Yan,Si, Lihui,Lin, Ruixin,Jin, Hongjuan,Jian, Wenwen,Yu, Qing,Yang, Shuli
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- New 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives: Facile synthesis, biological evaluation and molecular docking study
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Abstract: An efficient ultrasound-promoted one-pot three-component synthesis of a series of new 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives as antifungal and antioxidant agents using NaHCO3 has been described for the first time. T
- Khare, Smita P.,Deshmukh, Tejshri R.,Akolkar, Satish V.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 5159 - 5182
(2019/07/04)
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- Ultrasound assisted rapid synthesis, biological evaluation, and molecular docking study of new 1,2,3-triazolyl pyrano[2,3-c]pyrazoles as antifungal and antioxidant agent
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In search of new generation of triazole based antifungal agents, synthesis of series of new 1,2,3-triazolyl pyrano[2,3-c]pyrazoles under ultrasonic irradiation using NaHCO3 has been reported. The bioevaluation results indicate that, the compoun
- Khare, Smita P.,Deshmukh, Tejshri R.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 2521 - 2537
(2019/07/15)
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- Design, synthesis and biological evaluation of novel 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole triazole derivatives as potent TRPV1 antagonists
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Reported herein is the design, synthesis, and pharmacologic evaluation of a class of TRPV1 antagonists constructed on 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole as A-region and triazole as B-region. The SAR analysis indicated that 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole analogues displayed excellent antagonism of hTRPV1 activation by capsaicin and showed better potency compared to the corresponding dihydroindole analogues. Optimization of this design led to the eventual identification of 2-((1-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (6g), a potent TRPV1 antagonist. In vitro, using cells expressing recombinant human TRPV1 channels, 6g displayed potent antagonism activated by capsaicin (IC50 = 0.075 μM) and only partially blocked acid activation of TRPV1. In vivo, 6g exhibited good efficacy in capsaicin-induced and heat-induced pain models and had almost no hyperthermia side-effect. Furthermore, pharmacokinetic studies revealed that compound 6g had a superior oral exposure after oral administration in rats. To understand its binding interactions with the receptor, the docking study of 6g was performed in rTRPV1 model and showed an excellent fit to the binding site. On the basis of its superior profiles, 6g could be considered as the lead candidate for the further development of antinociceptive drugs.
- Li, Jinyu,Nie, Cunbin,Qiao, Yue,Hu, Jing,Li, Qifei,Wang, Qiang,Pu, Xiaohui,Yan, Lin,Qian, Hai
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p. 433 - 445
(2019/06/18)
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- RETRACTED ARTICLE: Synthesis, Molecular Properties, and Biological Evaluation of Hybrid 1,2,3-Triazolylpolyaza Heterocyclic Compounds
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In this research article, a highly efficient, cost-effective synthesis of various hybrid molecules possessing 1,2,3-triazolyltetrazoles and evaluation of their biological activity have been addressed. The structure elucidation of these new library hybrid molecules has been carried out by IR, 1H NMR, 13C NMR, and mass spectral analysis. The compounds have been screened for their anticancer activity against human colon cancer cell line Colo-205 and human lung cancer cell line HOP-205, and the results attest that most of the compounds have shown very good therapeutic nature. In particular, compounds 3d, 3j, 6a, and 6e were more cytotoxic than Adriamycin against all tested human cancer cell lines with 68percent, 101.8percent, 94percent, and 104.5percent growth, respectively. In the present investigation, a series of 3a–j and 6a–h were subjected to molecular properties prediction, drug likeness by Molinspiration, and toxicity risks by Molsoft software programs. All the 18 analogues were chosen on the basis of Lipinski “Rule of five” for the synthesis, screening their antibacterial and anticancer as oral bioavailable drugs/leads.
- Dasari, Srinivasa Rao,Tondepu, Subbaiah,Vadali, Lakshmana Rao,Ganivada, Mutyala Naidu,Seelam, Nareshvarma
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p. 195 - 208
(2019/01/04)
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- In vitro antiplasmodial efficacy of synthetic coumarin-triazole analogs
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Twenty two diverse coumarin-triazole derivatives were synthesized by alkylation of 7-hydroxy-4-methyl-coumarin followed by click chemistry at 7-position. These compounds were evaluated for their in vitro antiplasmodial activity against chloroquine sensitive strain of Plasmodium falciparum (3D7). Compound 9 (7-[1-(2, 4-dimethoxy-phenyl)-1H- [1–3] triazol-4-ylmethoxy]-4-methyl-chromen-2-one) was found most active with IC50 value 0.763 ± 0.0124 μg/mL. Further, the structure of compound 20 was characterized by single crystal X-ray diffraction. In view of impressive results, we considered it worthwhile to validate the results of in vitro antiplasmodial activity by assessing whether these compounds are capable of hampering the catalytic activity of DNA gyrase, thus preventing its supercoiling function.
- Yadav, Neesha,Agarwal, Drishti,Kumar, Satyanand,Dixit,Gupta, Rinkoo D.,Awasthi, Satish K.
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p. 735 - 745
(2018/02/06)
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- Use of an efficient polystyrene-supported cerium catalyst for one-pot multicomponent synthesis of spiro-piperidine derivatives and click reactions in green solvent
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One-pot multicomponent reactions are very demanding in synthetic organic chemistry. Here we report a new polystyrene-supported cerium catalyst (PS-Ce-amtp) obtained via an easy two-step procedure, which was thoroughly characterized using various techniques. PS-Ce-amtp catalyses the environmentally benign one-pot multicomponent synthesis of spiro-piperidine derivatives through the reaction of substituted aniline, cyclic active methylene compound and formaldehyde at room temperature. The catalyst also exhibits excellent catalytic activity in one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction between in situ generated azides (derived from anilines and amines) and terminal alkynes. The catalyst can be recovered easily after reaction and reused five times without significant loss in its catalytic activity. The advantageous features of this catalyst are atom economy, operational simplicity, short reaction times, easy handling and high recycling efficiency.
- Mondal, Paramita,Ghosh, Swarbhanu,Das, Sabuj kanti,Bhaumik, Asim,Das, Debashis,Islam, Sk. Manirul
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- Triazole-diindolylmethane conjugates as new antitubercular agents: synthesis, bioevaluation, and molecular docking
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We describe the synthesis of novel triazole-incorporated diindolylmethanes (DIMs) using a molecular hybridization approach. The in vitro antitubercular activity of the DIMs against Mycobacterium tuberculosis H37Ra (ATCC 25177) was tested in the active and
- Danne, Ashruba B.,Choudhari, Amit S.,Chakraborty, Shakti,Sarkar, Dhiman,Khedkar, Vijay M.,Shingate, Bapurao B.
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supporting information
p. 1114 - 1130
(2018/08/01)
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- Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents
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Abstract: The synthesis of a new series of triazole-biscoumarin conjugates by using a molecular hybridization approach is described. The newly synthesized compounds 6a–k were evaluated for their in vitro antitubercular activity against active and dormant
- Danne, Ashruba B.,Choudhari, Amit S.,Sarkar, Dhiman,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 6283 - 6310
(2018/06/07)
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- Synthesis and biological evaluation of novel 3-O-tethered triazoles of diosgenin as potent antiproliferative agents
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Diosgenin, a promising anticancer steroidal sapogenin, was isolated from Dioscorea deltoidea. Keeping its stereochemistry rich architecture intact, a scheme for the synthesis of novel diosgenin analogues was designed using Cu (I)-catalysed alkyne-azide cy
- Masood-ur-Rahman,Mohammad, Younis,Fazili, Khalid Majid,Bhat, Khursheed Ahmad,Ara, Tabassum
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- Synthesis of Gallic-Acid-1-Phenyl-1H-[1,2,3]Triazol-4-yl Methyl Esters as Effective Antioxidants
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Using a click chemistry approach, a series of gallic-acid-1-phenyl-1H-[1,2,3]triazol-4-ylmethyl esters was synthesized to develop more effective antioxidants. The results of DPPH screening indicate that few of the synthesized analogs display better antioxidant effect compared to the standards. Among all, compounds, 9 and 20 displayed highest DPPH radical scavenging effect with IC50 values as low as 6.4±0.2 and 7.9±0.4 μM respectively, compared to the standard ascorbic acid (IC50=12±0.8 μM) and gallic acid (IC50=9.0±0.6 μM). Compound 10 also displayed a potent antioxidant effect with IC50 of 10.80±0.4 μM. This study provides an important aspect with regard to the use of these gallic-acid based synthetic antioxidants in food industry as dietary supplements.
- Lone, Shabir H.,Rehman, Shakeel U,Bhat, Khursheed A.
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p. 111 - 118
(2017/02/15)
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- General Method for the Synthesis of 1,4-Disubstituted 5-Halo-1,2,3-triazoles
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A general method for the synthesis of 1,4-disubstituted 5-halo-1,2,3-triazoles has been developed. The one-pot two-step process consists of a CuAAC reaction of a copper(I) acetylide with an organic azide catalyzed by (aNHC)CuCl, followed by halogenation with N-chlorosuccinimide, N-bromosuccinimide, or I2.
- Gribanov, Pavel S.,Topchiy, Maxim A.,Karsakova, Iuliia V.,Chesnokov, Gleb A.,Smirnov, Alexander Yu.,Minaeva, Lidiya I.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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supporting information
p. 5225 - 5230
(2017/09/29)
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- Highly efficient reduction of carbonyls, azides, and benzyl halides by NaBH4 in water catalyzed by PANF-immobilized quaternary ammonium salts
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A series of polyacrylonitrile fiber-supported quaternary ammonium salts (PANF-QAS) were prepared and applied to the catalytic reduction of aldehydes, ketones, azides, and benzyl halides in water using NaBH4 as the reducing reagent in a highly efficient, economic, and environmentally benign way. The structure-activity relationships were investigated, which showed that the catalysts made up of quaternary ammonium salts with longer alkyl chains, larger cationic radii and better lipophilicity speed up the reduction reaction to afford the products in excellent yield. Moreover, the optimized catalyst can be applied to the reduction of 1-naphthaldehyde in a continuous flow process with outstanding reactivity and recyclability.
- Du, Jianguo,Xu, Gang,Lin, Huikun,Wang, Guangwei,Tao, Minli,Zhang, Wenqin
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supporting information
p. 2726 - 2735
(2016/05/24)
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- Clickable 4-Oxo-β-lactam-Based Selective Probing for Human Neutrophil Elastase Related Proteomes
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Human neutrophil elastase (HNE) is a serine protease associated with several inflammatory processes such as chronic obstructive pulmonary disease (COPD). The precise involvement of HNE in COPD and other inflammatory disease mechanisms has yet to be clarified. Herein we report a copper-catalyzed alkyne–azide 1,3-dipolar cycloaddition (CuAAC, or ′click′ chemistry) approach based on the 4-oxo-β-lactam warhead that yielded potent HNE inhibitors containing a triazole moiety. The resulting structure–activity relationships set the basis to develop fluorescent and biotinylated activity-based probes as tools for molecular functional analysis. Attaching the tags to the 4-oxo-β-lactam scaffold did not affect HNE inhibitory activity, as revealed by the IC50values in the nanomolar range (56–118 nm) displayed by the probes. The nitrobenzoxadiazole (NBD)-based probe presented the best binding properties (ligand efficiency (LE)=0.31) combined with an excellent lipophilic ligand efficiency (LLE=4.7). Moreover, the probes showed adequate fluorescence properties, internalization in human neutrophils, and suitable detection of HNE in the presence of a large excess of cell lysate proteins. This allows the development of activity-based probes with promising applications in target validation and identification, as well as diagnostic tools.
- Ruivo, Eduardo F. P.,Gon?alves, Lídia M.,Carvalho, Luís A. R.,Guedes, Rita C.,Hofbauer, Stefan,Brito, José A.,Archer, Margarida,Moreira, Rui,Lucas, Susana D.
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supporting information
p. 2037 - 2042
(2016/10/22)
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- Promise of Retinoic Acid-Triazolyl Derivatives in Promoting Differentiation of Neuroblastoma Cells
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Retinoic acid induces differentiation in various types of cells including skeletal myoblasts and neuroblasts and maintains differentiation of epithelial cells. The present study demonstrates synthesis and screening of a library of retinoic acid-triazolyl derivatives for their differentiation potential on neuroblastoma cells. Click chemistry approach using copper(I)-catalyzed azide-alkyne cycloaddition was adopted for the preparation of these derivatives. The neurite outgrowth promoting potential of retinoic acid-triazolyl derivatives was studied on neuroblastoma cells. Morphological examination revealed that compounds 8a, 8e, 8f, and 8k, among the various derivatives screened, exhibited promising neurite-outgrowth inducing activity at a concentration of 10 μM compared to undifferentiated and retinoic acid treated cells. Further on, to confirm this differentiation potential of these compounds, neuroblastoma cells were probed for expression of neuronal markers such as NF-H and NeuN. The results revealed a marked increase in the NF-H and NeuN protein expression when treated with 8a, 8e, 8f, and 8k compared to undifferentiated and retinoic acid treated cells. Thus, these compounds could act as potential leads in inducing neuronal differentiation for future studies. (Chemical Equation Presented).
- Lone, Ali Mohd,Dar, Nawab John,Hamid, Abid,Shah, Wajaht Amin,Ahmad, Muzamil,Bhat, Bilal A.
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- Copper Acetate Catalyzed Regio-selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alk-ene Cycloaddition/Oxidation Approach
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A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity.
- Rohilla, Sandeep,Patel, Shyam Sunder,Jain, Nidhi
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p. 847 - 854
(2017/01/18)
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- An unprecedentedly simple method of synthesis of aryl azides and 3-hydroxytriazenes
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Fischer's approach towards the synthesis of aryl azides and triazinoles from diazonium salts and hydroxylammonium chloride (phenylhydraxylamine) was reinvestigated and optimized. The new methodology enables the preparation of aryl azides and triazinoles in high yields in water at room temperature. The procedure is very simple, robust, easily scalable, reproducible, and "green".
- Gribanov, Pavel S.,Topchiy, Maxim A.,Golenko, Yulia D.,Lichtenstein, Yana I.,Eshtukov, Artur V.,Terekhov, Vladimir E.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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p. 5984 - 5988
(2018/06/06)
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- CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry
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Abstract Copper(II) oxide (CuO) nanoparticles have been found to be an efficient catalyst for 1,3-dipolar cycloaddition (CuAAC) of aromatic azides and acetylenic xanthenes furnishing the corresponding xanthene substituted triazoles in excellent yields. Cu
- Iniyavan,Balaji,Sarveswari,Vijayakumar
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p. 5002 - 5009
(2015/08/04)
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- N, N -diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes
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Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.
- Xie, Sheng,Ramstr??m, Olof,Yan, Mingdi
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supporting information
p. 636 - 639
(2015/03/04)
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- Click chemistry inspired facile synthesis and bioevaluation of novel triazolyl analogs of Ludartin
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A convenient and modular synthesis involving diastereoselective Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction was carried out to furnish 1,4-disubstituted-1,2,3-triazoles of Ludartin. This reaction scheme involving Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction leading to the formation of triazolyl analogs is being reported for the first time. All the triazolyl products were characterised using spectral data analysis. Sulphorhodamine B cytotoxicity screening of the resulting products against a panel of five human cancerous cell-lines revealed that few of the analogs display promising broad spectrum cytotoxic effect. Among all the synthesized compounds, only 3q displayed the best cytotoxic effect with IC50 values of 12, 11, 38, 39 and 8.5 μM but less than the standard Ludartin (1) with IC50 values of 6.3, 7.4, 7.5, 6.9 and 0.5 μM against human neuroblastoma (T98G), lung (A-549), prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cell lines, respectively. The present synthesis was designed based on the previous literature reports of Ludartin as an aromatase inhibitor. Our work provides an initial study on structure-activity relationship of triazolyl analogs of sesquiterpene lactones in general and Ludartin (1) in particular.
- Lone, Shabir H.,Bhat, Khursheed A.,Majeed, Rabiya,Hamid, Abid,Khuroo, Mohd A.
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p. 1047 - 1051
(2014/03/21)
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- Synthesis of silver-graphene nanocomposite and its catalytic application for the one-pot three-component coupling reaction and one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles in water
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A graphene based composite with silver nanoparticles has been synthesized via a simple chemical route and its catalytic activity has been tested for multi-component reactions and click reaction in a one-pot approach. This silver-graphene nanocomposite sho
- Salam, Noor,Sinha, Arjyabaran,Roy, Anupam Singha,Mondal, Paramita,Jana, Nikhil R.,Islam, Sk Manirul
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p. 10001 - 10012
(2014/03/21)
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- Cu(II)-anchored functionalized mesoporous SBA-15: An efficient and recyclable catalyst for the one-pot Click reaction in water
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A new pyridine-imine functionalized mesoporus silica (SBA-15) has been synthesized through the Schiff-base condensation of 3-aminopropyl functionalized SBA-15 with 2-pyridinecarboxaldehyde followed by the grafting of Cu(II) onto it resulting a new Cu@PyIm-SBA-15 material. 2D-hexagonally ordered mesophases of the material are analyzed by small-angle powder X-ray diffractions (PXRD) and transmission electron microscopic (TEM) image analyses. The Cu(II)-anchored mesoporous material, Cu@PyIm-SBA-15 showed excellent catalytic activity towards the one pot click reaction between azides formed in situ from the corresponding amines and acetylenes in water at 0 C to room temperature resulting a wide variety of 1,4-disubstituted 1,2,3-triazoles. The catalyst has been recycled for five cycles without any appreciable loss of catalytic activity and also without any appreciable Cu-leaching, suggesting a future potential of this novel mesoporous catalyst for the synthesis of 1,4-disubstituted 1,2,3-triazoles.
- Roy, Susmita,Chatterjee, Tanmay,Pramanik, Malay,Roy, Anupam Singha,Bhaumik, Asim,Islam, Sk. Manirul
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- Efficient synthesis of 1,4-disubstituted triazolyl N-carboxamides via a simple and convenient MCR using basic alumina as solid support
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A microwave assisted green protocol for the synthesis of 1,4-disubstituted triazolyl N-carboxamides was explored using basic alumina as solid support. The method allows domino Ullmann-type reaction, Click reaction and formation of ester or amide linkages in a single reaction vessel using Cu(phen)(PPh 3)Br and CMPA as catalyst and basic alumina as solid support in high yield. The protocol did not require addition of any external ligands or base. The method was also found to be equally good for the synthesis of bis triazole adducts.
- Pal, Rammyani,Sarkar, Swarbhanu,Chatterjee, Nivedita,Sen, Asish Kumar
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p. 5642 - 5646
(2013/09/23)
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