31656-78-7

Basic information

• Product Name: 3-azidobenzonitrile
• Synonyms: 3-azidobenzonitrile
• CAS NO: 31656-78-7
• Molecular Weight: 144.136
• Mol File: 31656-78-7.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: 3-azidobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-azidobenzonitrile(31656-78-7)
• EPA Substance Registry System: 3-azidobenzonitrile(31656-78-7)

Safety Data

• Hazardous Substances Data: 31656-78-7(Hazardous Substances Data)

Upstream product

• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 2237-30-1 m-cyanoaniline 
• 619-24-9 3-nitrobenzonitrile 
• 54060-30-9 3-acetylenephenylamine 

Downstream Products

• 2237-30-1 m-cyanoaniline 
• 1286686-60-9 5-amino-1-(3-ethynylphenyl)-1H-1,2,3-triazole-4-carbonitrile 
• 1562441-45-5 C₂₅H₂₇N₅O₃ 
• 1354013-55-0 methyl 1-(3-cyanophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazole-4-carboxylate 
• 1354013-91-4 methyl 3-(3-cyanophenyl)-5-(trifluoromethyl)-3H-1,2,3-triazole-4-carboxylate 
• 1325725-18-5 5-(3-(4-(difluoromethyl)-1H-1,2,3-triazole-1-yl)phenyl)-1,3,4-thiadiazol-2-amine 
• 1325725-15-2 (4-(fluoromethyl)-1H-1,2,3-triazole-1-yl)benzonitrile 
• 1325725-17-4 (1-(3-(5-amino-1,3,4-thiadiazol-2-yl)phenyl)-1H-1,2,3-triazole-4-yl)methanol 
• 916150-99-7 4-carboxaldehyde-1-(3-cyanophenyl)-1H-1,2,3-triazole 
• 1215004-86-6 1-(3-cyanophenyl)-4-(pyridin-3-yl)-1H-1,2,3-triazole 
• 1246473-53-9 ethyl 1-(3-cyanophenyl)-5-(1-methylethyl)-1H-1,2,3-triazole-4-carboxylate 
• 1201666-82-1 3,3'-(1H-1,2,3-triazole-1,4-diyl)dibenzonitrile 
• 1201666-85-4 1-(3-cyanophenyl)-4-(4-cyanophenyl)-1H-1,2,3-triazole 
• 1201666-88-7 4-(5-cyano-2-methoxyphenyl)-1-(3-cyanophenyl)-1H-1,2,3-triazole 

Relevant articles and documents

Design, synthesis and biological evaluation of erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors

Inhibitors of poly (ADP-ribose) polymerase-1 (PARP-1) have shown to be promising in clinical trials against cancer, and many researchers are interested in the development of new PARP-1 inhibitors. Herein, we designed and synthesized 44 novel erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors. MTT assay results indicated that compound 10b had the most potent anti-proliferative activity against A549 cells among five cancer cells. The enzyme inhibitory activity in vitro of compound 10b was also significantly better than rucaparib. Furthermore, the selectivity index of compound 10b was higher than rucaparib for lung cancer cells. Flow cytometry analysis showed that compound 10b induced apoptosis of A549 cells by the mitochondrial pathway. Western blot analysis indicated that compound 10b was able to inhibit the biosynthesis of PAR effectively, and it was more potent than rucaparib. Also, compound 10b was able to up-regulate the ratio of bax/bcl-2, activate caspase-3, and ultimately induced apoptosis of A549 cells. The combined results revealed that the discovery of novel non-amide based PARP-1 inhibitors have great research significance and provide a better choice for the future development of drugs.

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.

Synthesis, characterization, and biological evaluation of new derivatives targeting MbtI as antitubercular agents

Tuberculosis (TB) causes millions of deaths every year, ranking as one of the most dangerous infectious diseases worldwide. Because several pathogenic strains of Mycobacterium tuberculosis (Mtb) have developed resistance against most of the established anti-TB drugs, new therapeutic options are urgently needed. An attractive target for the development of new antitubercular agents is the salicylate synthase MbtI, an essential enzyme for the mycobacterial siderophore biochemical machinery, absent in human cells. A set of analogues of I and II, two of the most potent MbtI inhibitors identified to date, was synthesized, characterized, and tested to elucidate the structural requirements for achieving an efficient MbtI inhibition and a potent antitubercular activity with this class of compounds. The structure-activity relationships (SAR) here discussed evidenced the importance of the furan as part of the pharmacophore and led to the preparation of six new compounds (IV-IX), which gave us the opportunity to examine a hitherto unexplored position of the phenyl ring. Among them emerged 5-(3-cyano-5-(trifluoromethyl)phenyl)furan-2-carboxylic acid (IV), endowed with comparable inhibitory properties to the previous leads, but a better antitubercular activity, which is a key issue in MbtI inhibitor research. Therefore, compound IV offers promising prospects for future studies on the development of novel agents against mycobacterial infections.