148869-66-3

Basic information

• Product Name: Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-
• CAS NO: 148869-66-3
• Molecular Formula: C9H7N5
• Molecular Weight: 185.188
• Mol File: 148869-66-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-(148869-66-3)
• EPA Substance Registry System: Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-(148869-66-3)

Safety Data

• Hazardous Substances Data: 148869-66-3(Hazardous Substances Data)

Upstream product

• 584-13-4 4-amino-1,2,4-triazole 
• 1194-02-1 4-fluorobenzonitrile 

Downstream Products

• 537674-63-8 4-[(3-benzyloxybenzyl)[1,2,4]triazol-4-ylamino]benzonitrile 
• 536974-64-8 4-[(4-benzyloxybenzyl)[1,2,4]triazol-4-ylamino]benzonitrile 
• 536974-79-5 4-[(2-bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile 
• 870779-69-4 4-[(3-hydroxy-phenylsulfanylmethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile 
• 1472068-03-3 4-[(2,3-difluoro-4-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino]-benzonitrile 
• 1472068-02-2 4-[(2,6-difluoro-4-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino]-benzonitrile 
• 1472068-01-1 4-[(2-fluoro-4-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino]benzonitrile 
• 1472068-08-8 3-bromo-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}phenyl benzoate 
• 1472068-04-4 4-[(2-chloro-4-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino]benzonitrile 
• 1472068-32-8 4-[(3-difluoromethyl-4-triisopropylsilanyloxybenzyl)-[1,2,4]triazol-4-ylamino]benzonitrile 
• 1472068-05-5 4-[(2,6-dichloro-4-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino]-benzonitrile 
• 1260369-08-1 4-[(4H-1,2,4-Triazol-4-yl){3-(tributylstannyl)benzyl}amino]benzonitrile 
• 1260369-03-6 4-((4H-1,2,4-triazol-4-yl)(4-(tributylstannyl)benzyl)amino)benzonitrile 
• 1260369-06-9 4-[{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl}(4H-1,2,4-triazol-4-yl)amino]benzonitrile 

Relevant articles and documents

First dual aromatase-steroid sulfatase inhibitors

Aromatase inhibitors in clinical use block the biosynthesis of estrogens. Hydrolysis of estrone 3-sulfate by steroid sulfatase is an important additional source of tumor estrogen, and blockade of both enzymes should provide a more effective endocrine therapy. Sulfamoylated derivatives of the aromatase inhibitor YM511 inhibited sulfatase and aromatase in JEG-3 cells with respective IC50 values of 20-227 and 0.82-100 nM (cf. letrozole, 0.89 nM). One dual inhibitor was potent against both enzymes in vivo, validating the concept.

LABELING COMPOUND FOR PET

A labeling compound of the present invention includes a structure represented by formula (1) wherein X1 is 11CH3, CH218F, CF218F, 18F, 76Br or 124/sup

Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl} phenylsulfamate: Synthesis, SAR, crystal structure, and in vitro and in vivo activities

The design and synthesis of a series of bicyclic ring containing dual aromatase-sulfatase inhibitors (DASIs) based on the aromatase inhibitor (AI) 4-[(4-bromobenzyl)(4H-1,2,4-triazol-4-yl)amino] benzonitrile are reported. Biological evaluation with JEG-3 cells revealed structure-activity relationships. The X-ray crystal structure of sulfamate 23 was determined, and selected compounds were docked into the aromatase and steroid sulfatase (STS) crystal structures. In the sulfamate-containing series, compounds containing a naphthalene ring are both the most potent AI (39, IC50AROM=0.25 nm) and the best STS inhibitor (31, IC50STS=26 nm). The most promising DASI is 39 (IC50AROM= 0.25 nm, IC50STS=205 nm), and this was evaluated orally in vivo at 10 mgkg-1, showing potent inhibition of aromatase (93%) and STS (93%) after 3 h. Potent aromatase and STS inhibition can thus be achieved with a DASI containing a bicyclic ring system; development of such a DASI could provide an attractive new option for the treatment of hormone-dependent breast cancer.