20442-96-0

Upstream product

• 619-50-1 4-nitrobenzoic acid methyl ester 
• 1174501-32-6 4-(methoxycarbonyl)phenylboronic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 
• 67-56-1 methanol 
• 6427-66-3 4-azidobenzoic acid 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 171364-80-0 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 31641-61-9 4-triphenylphosphoranylidenamino-benzoic acid methyl ester 
• 94563-12-9 methyl 4-((methoxycarbonyl)amino)benzoate 
• 94563-09-4 6-methoxycarbonyl-1-phenyl-3-phenylcarbamoyl-2-oxo-1,3-dihydrobenzimidazole 
• 5320-91-2 4,4'-bismethoxycarbonylazobenzene 
• 131035-57-9 methyl 3-hydroxy-4-(2,2,2-trifluoroacetamido)benzoate 
• 1402046-06-3 4-[5-[[(pyridin-2-ylmethyl)amino]methyl][1,2,3]triazol-1-yl]benzoic acid methyl ester 
• 1402045-94-6 4-[5-[(benzoyl-pyridin-2-ylmethylamino)methyl][1,2,3]triazol-1-yl]benzoic acid methyl ester 
• 1437656-46-6 4,4'-diethynyl-2,2'-bipyridine 
• 1380227-21-3 methyl 4-(4-(2-morpholino-4-oxo-1,4-dihydroquinolin-8-yl)-1H-1,2,3-triazol-1-yl)benzoate 

Relevant academic research and scientific papers

Structural modification of the aryl sulfonate ester of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, only one small molecule (cjoc42) has been identified to bind gankyrin, which simultaneously inhibits its interaction with the 26S proteasome. Despite this advance, 2nd generation inhibitors are needed to improve gankyrin binding and cellular efficacy. To this end, an extensive SAR for the aryl sulfonate ester moiety of the cjoc42 scaffold was explored, and showed that substitutions at the 2-, 3-, and 4-positions manifested significant increases in gankyrin binding, resulting in the most potent binders of gankyrin to date. Subsequent cell-based assay evaluation of our derivatives demonstrated antiproliferative activity against pediatric liver cancer cell lines Hep3B and HepG2, which was not previously observed for cjoc42.

Cu-Click Compatible Triazabutadienes to Expand the Scope of Aryl Diazonium Ion Chemistry

Triazabutadienes can be used to readily generate reactive aryl diazonium ions under mild, physiologically relevant conditions. These conditions are compatible with a range of functionalities that do not tolerate traditional aryl diazonium ion generation. To increase the utility of this aryl diazonium ion releasing chemistry an alkyne-containing triazabutadiene was synthesized. The copper-catalyzed azide-alkyne cycloaddition ("Cu-click") reaction was utilized to modify the alkyne-containing triazabutadiene and shown to be compatible with the nitrogen-rich triazabutadiene. One of the triazole products was tethered to a fluorophore, thus enabling the direct fluorescent labeling of a model protein.

White-Light Emission from Dual-Way Photon Energy Conversion in a Dye-Encapsulated Metal–Organic Framework

The design of white-light phosphors is attractive in solid-state lighting (SSL) and related fields. A new strategy in obtaining white light emission (WLE) from dual-way photon energy conversion in a series of dye?MOF (LIFM-WZ-6) systems is presented. Besi

Europium-Based Metal-Organic Framework as a Dual Luminescence Sensor for the Selective Detection of the Phosphate Anion and Fe3+ Ion in Aqueous Media

A new three-dimensional europium-based metal-organic framework has been synthesized with the newly designed ligand L (6-[1-(4-carboxyphenyl)-1H-1,2,3-triazol-4-yl]nicotinic acid). This compound acts as a dual sensor for the phosphate anion and Fe3+ ion in aqueous media. The mechanistic aspect of this selectivity and sensitivity was explored through several spectroscopic methods and then correlated with the corresponding structure.

Benzimidazole–galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation

We have obtained the X-ray crystal structure of the galectin-8 N-terminal domain (galectin-8N) with a previously reported quinoline–galactoside ligand at a resolution of 1.6 ?. Based on this X-ray structure, a collection of galactosides derivatised at O3 with triazole, benzimidazole, benzothiazole, and benzoxazole moieties were designed and synthesised. This led to the discovery of a 3-O-(N-methylbenzimidazolylmethyl)–galactoside with a Kd of 1.8 μM for galectin-8N, the most potent selective synthetic galectin-8N ligand to date. Molecular dynamics simulations showed that benzimidazole–galactoside derivatives bind the non-conserved amino acid Gln47, accounting for the higher selectivity for galectin-8N. Galectin-8 is a carbohydrate-binding protein that plays a key role in pathological lymphangiogenesis, modulation of the immune system, and autophagy. Thus, the benzimidazole-derivatised galactosides represent promising compounds for studies of the pathological implications of galectin-8, as well as a starting point for the development of anti-tumour and anti-inflammatory therapeutics targeting galectin-8.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

Chan-Lam-type Azidation and One-Pot CuAAC under CuI-Zeolite Catalysis

The copper(I)-exchanged zeolite CuI-USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy-to-prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional-group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one-pot CuI-catalyzed process.

New α-Hydroxy-1,2,3-triazoles and 9H-Fluorenes-1,2,3-triazoles: H Synthesis and Evaluation as Glycine Transporter 1 Inhibitors

Two series of new compounds containing 1,2,3-triazole moiety were designed as putative GlyT1 inhibitors aiming the discovery of new hits with activity in cognitive disorders. 1,4-Disubstituted α-hydroxy-1,2,3-triazoles were obtained as racemates in moderate to good yields by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click chemistry) as the key step between propargyl alcohols and aryl azides, previously prepared from anilines or boronic acids. Benzo[c]chromene-triazoles were planned to be obtained by palladium-catalyzed C?H activation using [bis(trifluoroacetoxy)iodobenzene] (PhI(TFA)2) of some α-hydroxy-1,2,3-triazoles, since benzo[c]chromenes are also privileged groups with several biological activities, including to the central nervous system. Unexpectedly, 9H-fluorenes-1,2,3-triazoles, instead of benzo[c]chromenetriazoles, were obtained by Friedel-Crafts alkylation reaction. The two series of compounds were tested for inhibition of the glycine transporter (rat GlyT1 isoform) but only the α-hydroxy-1,2,3-triazole 9b was active (half maximal inhibitory concentration (IC50) = 8.0 μM).

Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes

We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click"reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on"dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.