222716-19-0Relevant articles and documents
Novel 4-(1H-1,2,3-triazol-4-yl)methoxy)cinnolines as potent antibacterial agents: Synthesis and molecular docking study
Boda, Sathish Kumar,Bommagani, Mohan Babu,Chitneni, Prasad Rao,Mokenapelli, Sudhakar,Yerrabelli, Jayaprakash Rao
, (2020)
A new series of cinnoline-1,2,3-triazole derivatives were designed and synthesized by adopting Cu(1) catalyzed regeoselective1,3-dipolar cycloaddition reaction of terminal alkyne and azide. The in vitro antibacterial activity of all these compounds revealed that compounds 9d, 10a, 10b, and 10c are more potent antibacterial agents. Among the series, compound 4-(3-(4-((cinnolin-4-yloxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)morpholine (10b) exhibited the most potent antibacterial activity against all tested gram-positive and gram-negative bacterial strains. Furthermore, molecular docking studies were also performed to understand the binding interactions of the most active analogs 9d, 10a, 10b, and 10c with Elastase of Pseudomonas aeruginosa (PDB: 1U4G). The results indicated that these classes of compounds have potential antibacterial activity, especially the compound 10b may serve as a promising antibacterial lead compound that could be further optimized for the further development of antibacterial drugs.
Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide-Mediated Polymerization
Tesch, Matthias,Kudruk, Sergej,Letzel, Matthias,Studer, Armido
, p. 5915 - 5919 (2017)
Nitroxide-mediated polymerization (NMP) was applied to prepare alternating copolymers using 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) 1 and ((6-trimethylsilyl)-hex-5-yn-1-yl)vinyl ether (THVE) 2 as monomers. The alternating sequence of the resulting poly(HFIPA-alt-THVE) 3 was proved by using tandem mass spectrometry (MS/MS) and further supported by 1H NMR spectroscopy. Alternating alkyne and activated ester moieties of copolymer 3 were further functionalized with organic azides and amines using sequential Cu-catalyzed azide–alkyne click (CuAAC) and amidation reactions, providing dually functionalized poly(acrylamide-alt-triazole) polymers 5. Water-soluble alternating poly(acrylic acid-alt-triazole) copolymers 9 were obtained by saponification of HFIP esters. 1H and 19F NMR spectroscopy, IR spectroscopy as well as gel permeation chromatography (GPC) were used to characterize the polymers before and after functionalization.
Design and synthesis of novel diosgenin-triazole hybrids targeting inflammation as potential neuroprotective agents
Huang, Yi,Huang, Weiwei,Yang, Guixiang,Wang, Rui,Ma, Lei
supporting information, (2021/05/21)
Alzheimer's disease is a progressive neurodegenerative disease, and its incidence is expected to increase as the global population ages. Recent studies provide increasing evidence that inflammation plays a key role in the pathogenesis and progression of AD. Diosgenin, an active ingredient in Dioscorea nipponica Makino, is a promising bioactive lead compound in the treatment of Alzheimer's disease, which exhibited anti-inflammatory activity. To search for more efficient anti-Alzheimer agents, a series of novel diosgenin-triazolyl hybrids were designed, synthesized, and their neuroprotective effects against oxygen-glucose deprivation-induced neurotoxicity and LPS-induced NO production were evaluated. Most of these new hybrids displayed better activities than DIO. In particular, the promising compound L6 not only demonstrated an excellent neuroprotective effect but also showed the best anti-inflammatory activity. The structure-activity relationship study illustrated that the introduction of benzyl or phenyl triazole did improve the activity, and the introduction of benzyl triazole was better than that of phenyl triazole. The results we obtained showed that the diosgenin skeleton could be a promising structural template for the development of new anti-Alzheimer drug candidates, and compound L6 has the potential to be an important lead compound for further research.
Synthesis and comparison of in vitro dual anti-infective activities of novel naphthoquinone hybrids and atovaquone
Erasmus, Chané,Aucamp, Janine,Smit, Frans J.,Seldon, Ronnett,Jordaan, Audrey,Warner, Digby F.,N'Da, David D.
supporting information, (2021/07/06)
A principal factor that contributes towards the failure to eradicate leishmaniasis and tuberculosis infections is the reduced efficacy of existing chemotherapies, owing to a continuous increase in multidrug-resistant strains of the causative pathogens. Th
Synthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cells
Dias, Maria C.F.,de Sousa, Bianca L.,Ionta, Marisa,Teixeira, Róbson R.,Goulart, Thiago Q.,Ferreira-Silva, Guilherme á.,Pilau, Eduardo J.,dos Santos, Marcelo H.
, p. 572 - 587 (2021/02/12)
Benzophenones display several biological activities, including antioxidant, anticancer, and photoprotective. Furthermore, antioxidants can minimize both ultraviolet absorption and tumor development. In the present investigation, a series of twenty-six 1,2
Discovering High Potent Hsp90 Inhibitors as Antinasopharyngeal Carcinoma Agents through Fragment Assembling Approach
Xu, Mengyang,Zhao, Chao,Zhu, Biying,Wang, Liangyue,Zhou, Huihao,Yan, Daoguang,Gu, Qiong,Xu, Jun
, p. 2010 - 2023 (2021/02/16)
Hsp90 is a new promising target for cancer treatment. Many inhibitors have been discovered as therapeutic agents, and some have passed Phase I and II. However, no one is approved by FDA yet. Novel and druggable Hsp90 inhibitors are still demanding. Here,
Synthesis of new derivatives of alepterolic acid via click chemistry
Aisa, Haji Akber,Cao, Jianguo,Guo, Hongmei,Huang, Guozheng,Jin, Xin,Wang, Qi,Zhao, Qingjie
, p. 917 - 925 (2021/11/16)
Alepterolic acid is a natural diterpenoid isolated from Aleuritopteris argentea (S. G. Gmél.) Fée, a fern with potential medicinal activity, used in China as a folk medicine to regulate menstruation and prevent cancer. Nevertheless, there are few reports
Inverted positioning of dnmt1 inhibitor in the active site of dnmt1 caused by hydrophobicity/hydrophilicity of the terminal structure
Kondo, Takeshi,Kubo, Yuhei,Tojo, Toshifumi,Yuasa, Makoto
, p. 2372 - 2378 (2021/12/16)
DNA (cytosine-5)-methyltransferase 1 (DNMT1) is one of the enzymes that regulate DNA modification. It has been demonstrated that overexpression of DNMT1 is associated with the development of cancer, making DNMT1 an attractive molecular target for cancer t
Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
supporting information, p. 9047 - 9052 (2021/12/06)
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
Discovery of a Series of Theophylline Derivatives Containing 1,2,3-Triazole for Treatment of Non-Small Cell Lung Cancer
Li, Qingjiao,Liu, Yulin,Mao, Longfei,Peng, Lizeng,Xie, Luoyijun,Yang, Jianxue,Ye, Jiahui,Yuan, Miaomiao,Zhang, Rongjun
, (2021/11/16)
Chemotherapy is the most common clinical treatment for non-small cell lung cancer (NSCLC), but low efficiency and high toxicity of current chemotherapy drugs limit their clinical application. Therefore, it is urgent to develop hypotoxic and efficient chemotherapy drugs. Theophylline, a natural compound, is safe and easy to get, and it can be used as a modified scaffold structure and hold huge potential for developing safe and efficient antitumor drugs. Herein, we linked theophylline with different azide compounds to synthesize a new type of 1,2,3-triazole ring-containing theophylline derivatives. We found that some theophylline1,2,3-triazole compounds showed a good tumor-suppressive efficacy. Especially, derivative d17 showed strong antiproliferative activity against a variety of cancer cells in vitro, including H460, A549, A2780, LOVO, MB-231, MCF-7, OVCAR3, SW480, and PC-9. It is worth noting that the two NSCLC cell lines H460 H and A549 are sensitive to compound d17 particularly, with IC50 of 5.929 ± 0.97?μM and 6.76 ± 0.25?μM, respectively. Compound d17 can significantly induce cell apoptosis by increasing the ratio of apoptotic protein Bax/Bcl-2 by downregulating the expression of phosphorylated Akt protein, and it has little toxicity to normal hepatocyte cells LO2 at therapeutic concentrations. These data indicate that these theophylline acetic acid-1,2,3-triazole derivatives may be potential drug candidates for anti-NSCLC and are worthy of further study.
