31656-92-5

Usage

InChI:InChI=1/C7H7N3/c1-6-4-2-3-5-7(6)9-10-8/h2-5H,1H3

Upstream product

• 2028-34-4 o-toluene-diazonium chloride 
• 95-53-4 o-toluidine 
• 7664-41-7 ammonia 
• 67-56-1 methanol 
• 116569-11-0 o-tolyl-pentazole 
• 95-46-5 2-methylphenyl bromide 
• 615-37-2 ortho-methylphenyl iodide 
• 16419-60-6 2-Methylphenylboronic acid 
• 635-26-7 o-tolylhydrazine hydrochloride 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 88-72-2 1-methyl-2-nitrobenzene 
• 13194-68-8 4-iodo-2-methylaniline 
• 31553-17-0 1-azido-2-(bromomethyl)benzene 

Downstream Products

• 103989-34-0 5-methyl-1-(2-methylphenyl)-1,2,3-triazol-4-carboxylic acid 
• 108840-86-4 4-phenyl-1-o-tolyl-1H-1,2,3-triazol-5-amine 
• 81945-56-4 1-(2-methylphenyl)-1H-1,2,3-triazole 
• 128654-38-6 9-(o-tolyl)-9-azabicyclo<6.1.0>nonane 
• 75794-20-6 4-amino-3-methylphenyl methyl sulphide 
• 100305-95-1 2-amino-3-methylphenyl methyl sulphide 
• 95-53-4 o-toluidine 
• 128677-60-1 8-(o-tolyl)-8-azabicyclo<5.1.0>octane 
• 73078-98-5 C₂₂H₁₇N₃O 
• 73078-85-0 C₃₇H₂₇NO₂ 
• 65244-34-0 C₁₈H₂₁N₅O₄ 
• 65245-61-6 C₁₄H₁₅N₅ 
• 31553-17-0 1-azido-2-(bromomethyl)benzene 
• 5405-13-0 N-benzyl-2-methylaniline 

Relevant academic research and scientific papers

Synthesis, antiproliferative, docking and DFT studies of benzimidazole derivatives as EGFR inhibitors

In the present work, new benzimidazole linked 1,2,3-triazole hybrids have been synthesized and screened for antiproliferative and EGFR kinase inhibitory activities.The structures of these hybrids were elucidated using IR, NMR, mass spectrometry and elemen

Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids

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.].

2-((1-Phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives: Simplification and modification of aconitine scaffold for the discovery of novel anticancer agents

The molecular chaperone heat shock protein 90 (Hsp90) is a promising target for cancer therapy. Natural product aconitine is a potential Hsp90 inhibitor reported in our previous work. In this study, we designed and synthesized a series of 2-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives as potent Hsp90 inhibitors by simplifying and modifying aconitine scaffold. Among these compounds, 14t exhibited an excellent antiproliferative activity against LoVo cells with an IC50 value of 0.02 μM and a significant Hsp90α inhibitory activity with an IC50 value of 0.71 nM. Molecular docking studies provided a rational binding model of 14t in complex with Hsp90α. The following cell cycle and apoptosis assays revealed that compound 14t could arrest cell cycle at G1/S phase and induce cell apoptosis via up-regulation of bax and cleaved-caspase 3 protein expressions while inhibiting the expressions of bcl-2. Moreover, 14t could inhibit cell migration in LoVo and SW620 cell lines. Consistent with in vitro results, 14t significantly repressed tumor growth in the SW620 xenograft mouse model.

Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold

In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.

Design, synthesis and molecular docking studies of thymol based 1,2,3-triazole hybrids as thymidylate synthase inhibitors and apoptosis inducers against breast cancer cells

Natural product produced by plants has been the backbone for numerous anticancer agents. In the present work, natural bioactive thymol based 1,2,3-triazole hybrids have been synthesized and evaluated for anticancer activity in MCF-7 and MDA-MB-231 cancer

Design, synthesis and photoluminescent studies of new 1,5-benzodiazepines derivatives: Towards new ESIPT compounds

A series of novel N1-triazolo-4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-ones 7a-e and N5-triazolo-4-(2-acetoxyphenyl)-1,5-benzodiazepin-2-ones 8a-e were designed and synthesized in good yields via a Cu(I) catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC) between the N1- and N5-propargyl-1,5-benzodiazepines 2 and 5 respectively and various arylazides 6a-e. Photophysical properties were investigated for all the obtained triazolo-benzodiazepine hybrids by mean of absorption and fluorescence spectral techniques. Thus, a fluorescent emission was detected for the derivatives 7a-e in aggregated state. On another hand, the O-acetylated derivatives 8a-e were found to be not emissive. Finally, we have chosen a model reaction to demonstrate that upon deprotecting the -OAc group in the N1, N5-disubstituted benzodiazepine 8d a moderate fluorescence reappeared in the obtained product 9d proving that an ESIPT process can take place as long as the hydroxyl group remains free, allowing the OH/C[dbnd]O proton transfer to occur. A computational study of compounds 7e and 9d in vacuo provide further details and arguments to rationalize the fluorescence of these compounds in aqueous mixtures.

Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol

A new series of diverse triazoles linked to the hydroxyl group of totarol were synthesized using click chemistry approach. The structures of these compounds were elucidated by HRMS, IR and NMR spectroscopy. The structure of compound 3 g was also confirmed by x-ray single crystal diffraction. The cytotoxicity of these compounds was evaluated by the MTT method against four cancer cell lines, including fibrosarcoma HT-1080, lung carcinoma A-549 and breast adenocarcinoma (MDA-MB-231 and MCF-7), and the results indicated that all compounds showed weak to moderate activities against all cancer cell lines with IC50 values ranging from 14.44 to 46.25 μM. On the basis of our research the structure–activity relationships (SAR) of these compounds were discussed. This work provides some important hints for further structural modification of totarol towards developing novel and highly effective anticancer drugs respectively. It is interesting to note that compound 3 g indicated a very significant cytotoxicity against HT-1080 and A-549 cell lines. The molecular docking showed that compound 3 g activated the caspase-3 and inhibited tubulin by forming stable protein–ligand complexes.

Synthesis of new derivatives of alepterolic acid via click chemistry

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

Biofilm inhibition and DNA binding studies of isoxazole-triazole conjugates in the development of effective anti-bacterial agents

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.

Design, synthesis and biological evaluation of homoerythrina alkaloid derivatives bearing a triazole moiety as PARP-1 inhibitors and as potential antitumor drugs

A series of homoerythrina alkaloid derivatives containing a 1,2,3-triazole moiety as PARP-1 inhibitors were designed and synthesized. And their anti-proliferative activity was further evaluated. Compound 10n had excellent activity to inhibit proliferation of A549 cells (IC50 = 1.89 μM), which was higher than harringtonine (IC50 = 10.55 μM), pemetrexed (IC50 = 3.39 μM), and rucaparib (IC50 = 4.91 μM). Furthermore, the selectivity index of compound 10n was higher than rucaparib and pemetrexed for lung cancer cells. Flow cytometry analysis showed that compound 10n significantly arrested the cell cycle in the S phase, then induced apoptosis of A549 cells (apoptosis rate is 46%), which effectively inhibited cell proliferation. Simultaneously, western blot analysis revealed that compound 10n could prevent the biosynthesis of PAR. Further analysis results revealed that compound 10n could inhibit the expression of cyclin A, down-regulate the expression of bcl-2/bax, activate caspase-3, and ultimately induce apoptosis of A549 cells. All the results indicated that compound 10n had potential research value as a novel PARP-1 inhibitor in antitumor, and it provided a new reference for further development of PARP-1 inhibitors.