1218-69-5

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the production of Deferasirox.

InChI:InChI=1/C14H9NO3/c16-11-7-3-1-5-9(11)14-15-13(17)10-6-2-4-8-12(10)18-14/h1-8,16H

Upstream product

• 65-45-2 salicylamide 
• 69-72-7 salicylic acid 
• 1441-87-8 salicyloyl chloride 
• 141-43-5 ethanolamine 
• 63963-47-3 6,6'-(1,2,4-Dithiazolidin-3,5-yliden)-bis-2,4-cyclohexadien-1-on 
• 13316-79-5 O-Benzoylsalicylamide 
• 3084-52-4 2-phenyl-4H-1,3-benzoxazin-4-one 
• 98-88-4 benzoyl chloride 
• 1972-71-0 2-hydroxy-N-(2-hydroxybenzoyl)benzamide 

Downstream Products

• 201530-41-8 deferasirox 
• 86245-87-6 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzene 
• 201530-46-3 3,5-Bis(2-hydroxyphenyl)-1-(2,4-difluorophenyl)-1H-[1,2,4]triazole 
• 201530-38-3 3,5-bis(2-hydroxyphenyl)-1-(2,2,2-trifluoroethyl)-1H-[1,2,4]triazole 
• 201530-47-4 3,5-bis(2-hydroxyphenyl)-1-benzyl-1H-[1,2,4]triazole 
• 55920-00-8 [4,6-bis-(2-hydroxy-phenyl)-[1,3,5]triazin-2-yl]-urea 
• 1262725-38-1 C₂₂H₁₄N₄O₂ 
• 1262725-37-0 C₂₃H₁₇N₃O₄ 
• 1262725-40-5 C₂₂H₁₅N₃O₄ 
• 1262725-42-7 C₂₈H₂₇N₃O₄ 
• 1133425-75-8 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]-[2,3,5,6-²H₄]benzoic acid 
• 872005-50-0 4-(3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl)benzoyl chloride 

Relevant academic research and scientific papers

Deferasirox (ExJade): An FDA-Approved AIEgen Platform with Unique Photophysical Properties

Deferasirox, ExJade, is an FDA-approved iron chelator used for the treatment of iron overload. In this work, we report several fluorescent deferasirox derivatives that display unique photophysical properties, i.e., aggregation-induced emission (AIE), excited state intramolecular proton transfer, charge transfer, and through-bond and through-space conjugation characteristics in aqueous media. Functionalization of the phenol units on the deferasirox scaffold afforded the fluorescent responsive pro-chelator ExPhos, which enabled the detection of the disease-based biomarker alkaline phosphatase (ALP). The diagnostic potential of these deferasirox derivatives was supported by bacterial biofilm studies.

Synthesis of novel 2,4-Di(o-hydroxyphenyl)-6-substituted amino-1,3,5-triazine

Seven novel 1,3,5-triazine derivatives were synthesized in good to high yields (69.19-91.15%) by the reaction of substituted guanidine with 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one in ethanol. The products were recrystallized from ethanol or ethanol-DMF mixture and their structures were confirmed by 1H NMR and FT-IR.

Synthesis of deuterium-labelled isotopomer of deferasirox

A d4-labeled isotopomer of deferasirox was synthesized as internal standard for use in a LC/mass spectroscopy (MS)/MS method developed for the simultaneous quantitative determination of deferasirox in human serum. d4-deferasirox was synthesized from d8-toluene.

Excitation Wavelength Dependent Fluorescence of an ESIPT Triazole Derivative for Amine Sensing and Anti-Counterfeiting Applications

Excitation wavelength dependent (Ex-De) emission materials have potential applications in anti-counterfeiting labels and bioimaging. Nevertheless, few purely organic chromophores are used in these areas. In this study, multiple excited states were incorporated into a molecule that was excited state intramolecular proton transfer (ESIPT) active, with the goal of manipulating the relaxation pathways of the excited states. The triazole derivative exhibits Ex-De photoluminescence (PL), and the maximum PL wavelength is located at 526 nm and 593 nm under a series of excitation wavelengths. Spectral identification indicates that the excimer and ESIPT processes are responsible for the green (526 nm) and orange (593 nm) fluorescence, respectively. Importantly, the quick response code and test strip prepared with this triazole derivative can be used for anti-counterfeiting and food spoilage detection applications, respectively. This research opens the door for developing novel Ex-De materials for anti-counterfeiting purposes.

Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4-Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate

A series of new deferasirox derivatives were synthesized through the reaction of monosubstituted hydrazides with 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one. For the first time, deferasirox and some of its derivatives were evaluated for their in vitro inhibitory activity against Jack bean urease. The potencies of the members of this class of compounds are higher than that of acetohydroxamic acid. Two compounds, bearing tetrazole and hydrazine derivatives (bioisoester of carboxylate group), represented the most potent urease inhibitory activity with IC50 values of 1.268 and 3.254 μm, respectively. In silico docking studies were performed to delineate possible binding modes of the compounds with the enzyme, urease. Docking analysis suggests that the synthesized compounds were anchored well in the catalytic site and extending to the entrance of binding pocket and thus restrict the mobility of the flap by interacting with its crucial amino acid residues, CME592 and His593. The overall results of urease inhibition have shown that these target compounds can be further optimized and developed as a lead skeleton for the discovery of novel urease inhibitors.

A triazole based fluorescence "turn-on" sensor for Al(III) and Zn(II) ions

A triazole derivative containing trifluoromethyl and diphenol unit was synthesized as a fluorescent 'turn-on' chemosensor for Al3+ and Zn2+ ions with high sensitivity, a rapid response time and specific selectivity over other cations.

In vitrostudies of deferasirox derivatives as potential organelle-targeting traceable anti-cancer therapeutics

We report here strategic functionalization of the FDA approved chelator deferasirox (1) in an effort to produce organelle-targeting iron chelators with enhanced activity against A549 lung cancer cells. Derivative 8 was found to have improved antiproliferative activity relative to 1. Fluorescent cell imaging revealed that compound 8 preferentially localises within the lysosome.

Synthesis and biological evaluation of 1,2,4-oxadiazole core derivatives as potential neuroprotectants against acute ischemic stroke

Here, we report the synthesis and neuroprotective capacity of 27 compounds with a bisphenol hydroxyl-substituted 1,2,4-triazole core or 1,2,4-oxadiazole core for stroke therapy. In vitro studies of the neuroprotective effects of compounds 1–27 on sodium nitroprusside (SNP)-induced apoptosis in PC12 cells indicate that compound 24 is the most effective compound conferring potent protection against oxidative injury. Compound 24 inhibits reactive oxygen species (ROS） accumulation and restores the mitochondrial membrane potential (MMP). Moreover, further analysis of the mechanism showed that compound 24 activates the antioxidant defence system by promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2) and increasing the expression of haem oxygenase 1 (HO-1). An in vivo study was performed in a rat model of transient focal cerebral ischaemia generated by the intraluminal occlusion of the middle cerebral artery (MCAO). Compound 24 significantly reduced brain infarction and improved neurological function. Overall, compound 24 potentially represents a promising compound for the treatment of stroke.

Synthesis and biological evaluation of 1,2,4-triazole derivatives as potential neuroprotectant against ischemic brain injury

A series of 1,2,4-triazole derivatives 1–14 was synthesized to investigate their neuroprotective effects and mechanisms of action. Compounds 5–11 noticeably protected PC12 cells from the cytotoxicity of H2O2 or sodium nitroprusside (SNP). Compound 11 was the most effective derivative. Compound 11 chelated Fe (II) iron, scavenged reactive oxygen species (ROS), and restored the mitochondrial membrane potential (MMP). Moreover, it enhanced the activity of the antioxidant defense system by increasing the serum level of superoxide dismutase (SOD) and promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2). Compound 11 caused certain improvements in behavior, the cerebral infarction area, and serum levels of biochemical indicators (TNF-α, IL-1β, SOD and MDA) in a rat MCAO model. The lethal dose (LD50) of compound 11 in mice receiving intraperitoneal injections was greater than 400 mg/kg. Meanwhile, pharmacokinetic experiments revealed high bioavailability of this compound after both oral and intravenous administration (F = 60.76%, CL = 0.014 mg/kg/h) and a longer half-life (4.26 and 5.11 h after oral and intravenous administration, respectively). Based on these findings, compound 11 may be a promising neuroprotectant for the treatment of ischemic stroke.

NEW PYRIDINE AND PYRIMIDINE SUBSTITUTED TRIAZINE UV ABSORBERS

A compound of formula (1), wherein V, W, X and Y represent N or CH, at least one of V, W, X and Y being N and at least two of V, W, X and Y being CH; and R1, R2 and R3 are each independently of the other hydrogen, C1-C8alkyl, C1-C8alkoxy, nitro, cyano, trifluoromethyl, halogen or hydroxy; with the proviso that the compounds of formulae (101) and (102) are excluded, provides good lightfastness properties to textile fibre materials, in particular PES fibre materials.