70659-90-4

Upstream product

• 589-10-6 phenoxyethyl bromide 
• 622-86-6 2-chloroethoxybenzene 
• 141482-06-6 1-methanesulfonyloxy-2-(phenoxy)ethane 
• 108-95-2 phenol 
• 122-99-6 2-Phenoxyethanol 
• 43224-81-3 2-phenoxyethanol tosylate 

Downstream Products

• 405-97-0 2-phenoxy-1-fluoroethane 
• 1758-46-9 2-phenoxyethanamine 
• 1092115-78-0 (E)-N-(4-methoxybenzyloxy)-3-(1-(2-phenoxyethyl)-1H-1,2,3-triazol-4-yl)acrylamide 
• 1092115-92-8 1-(2-phenoxy-ethyl)-1H-[1,2,3]triazole-4-carboxylic acid (4-methoxy-benzyloxy)-amide 
• 1233641-52-5 GO-Y₀₈₈ 
• 1246847-80-2 C₁₇H₁₇N₃O₂ 
• 1360180-60-4 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(3-((1-(2-phenoxyethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide 
• 1359754-69-0 3-(1H-indol-3-yl)-4-(1-(2-phenoxyethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 
• 1390650-84-6 5-iodo-1-(2-phenoxyethyl)-4-phenyl-1H-1,2,3-triazole 
• 1431375-50-6 C₂₄H₂₄N₆O₄ 
• 1431375-62-0 4-cyclohex-1-en-1-yl-5-iodo-1-(2-phenoxyethyl)-1H-1,2,3-triazole 

Relevant academic research and scientific papers

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.].

COMPOUNDS FOR THE INHIBITION OF INDOLEAMINE-2,3-DIOXYGENASE ACTIVITY AND USE THEREOF

The present invention relates to compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of indoleamine-2,3-dioxygenase (IDO) activity, and methods of treating IDO-related disorders.

Bodipy-squaraine triads: Preparation and study of the intramolecular energy transfer, charge separation and intersystem crossing

Two triads (BDP-SQ and Styryl-BDP-SQ) were prepared with Bodipy, styrylBodipy and Squaraine (SQ) units. SQ shows unexpected efficient intersystem crossing (ISC. ΦT = 50%), which is attributed to S1→T1 transition. In the two triads, the F?rster Resonance Energy Transfer (FRET) direction, as well as the spatial localization of the T1 state, was judiciously tuned. The cascade photophysical properties of the triads were studied with steady-state and time-resolved optical spectroscopies, as well as with electrochemical characterization and theoretical computations. We show that triplet state was produced in triad BDP-SQ upon photoexcitation, but in Styryl-BDP-SQ the fast FRET and the charge separation (CS) processes compete with the ISC of the SQ unit, and no triplet state was formed upon photoexcitation. The singlet energy transfer kinetics were found to be 1.6 and 0.6 ps, respectively and are solvent polarity dependent. Charge transfer was confirmed with ultrafast transient absorption spectroscopy.

Activity of Fluorine-Containing Analogues of WC-9 and Structurally Related Analogues against Two Intracellular Parasites: Trypanosoma cruzi and Toxoplasma gondii

Two obligate intracellular parasites, Trypanosoma cruzi, the agent of Chagas disease, and Toxoplasma gondii, an agent of toxoplasmosis, upregulate the mevalonate pathway of their host cells upon infection, which suggests that this host pathway could be a potential drug target. In this work, a number of compounds structurally related to WC-9 (4-phenoxyphenoxyethyl thiocyanate), a known squalene synthase inhibitor, were designed, synthesized, and evaluated for their effect on T. cruzi and T. gondii growth in tissue culture cells. Two fluorine-containing derivatives, the 3-(3-fluorophenoxy)- and 3-(4-fluorophenoxy)phenoxyethyl thiocyanates, exhibited half-maximal effective concentration (EC50) values of 1.6 and 4.9 μm, respectively, against tachyzoites of T. gondii, whereas they showed similar potency to WC-9 against intracellular T. cruzi (EC50values of 5.4 and 5.7 μm, respectively). In addition, 2-[3- (phenoxy)phenoxyethylthio]ethyl-1,1-bisphosphonate, which is a hybrid inhibitor containing 3-phenoxyphenoxy and bisphosphonate groups, has activity against T. gondii proliferation at sub-micromolar levels (EC50=0.7 μm), which suggests a combined inhibitory effect of the two functional groups.

Preparation of Bodipy-ferrocene dyads and modulation of the singlet/triplet excited state of bodipy: Via electron transfer and triplet energy transfer

Modulation of the singlet/triplet excited state of a fluorophore is becoming more important for molecular switches, molecular memory devices, chemical or biological sensors and controllable photodynamic therapy (PDT) etc. Boron-dipyrromethene (Bodipy)-ferrocene (Fc) dyads were prepared for reversible electrochemical switching of the singlet excited state (fluorescence), as well as the triplet excited states of Bodipy. The photophysical properties of the dyads were studied using steady-state UV-vis absorption spectroscopy, fluorescence, electrochemical characterization, time-resolved fluorescence and nanosecond transient absorption spectroscopies. The fluorescence of the Bodipy moieties in the dyads was quenched significantly, due to the photo-induced electron transfer (PET). This conclusion was supported by electrochemical characterization and calculation of the Gibbs free energy changes of PET. We demonstrated that the fluorescence of the Bodipy moiety can be reversibly switched ON and OFF by electrochemical oxidation of the Fc moiety (Fc/Fc+). Furthermore, we proved that the Fc moiety is efficient for quenching of the triplet excited states of Bodipy. Two quenching mechanisms, PET and triplet-triplet-energy transfer (TTET), are responsible for the intramolecular and intermolecular quenching of the triplet excited states of the diiodoBodipy unit.

Synthesis and Evaluation of a Library of Trifunctional Scaffold-Derived Compounds as Modulators of the Insulin Receptor

We designed a combinatorial library of trifunctional scaffold-derived compounds, which were derivatized with 30 different in-house-made azides. The compounds were proposed to mimic insulin receptor (IR)-binding epitopes in the insulin molecule and bind to and activate this receptor. This work has enabled us to test our synthetic and biological methodology and to prove its robustness and reliability for the solid-phase synthesis and testing of combinatorial libraries of the trifunctional scaffold-derived compounds. Our effort resulted in the discovery of two compounds, which were able to weakly induce the autophosphorylation of IR and weakly bind to this receptor at a 0.1 mM concentration. Despite these modest biological results, which well document the well-known difficulty in modulating protein-protein interactions, this study represents a unique example of targeting the IR with a set of nonpeptide compounds that were specifically designed and synthesized for this purpose. We believe that this work can open new perspectives for the development of next-generation insulin mimetics based on the scaffold structure.

BODIPY triads triplet photosensitizers enhanced with intramolecular resonance energy transfer (RET): Broadband visible light absorption and application in photooxidation

Resonance energy transfer (RET) was used to enhance the light absorption in triad triplet photosensitizers to access strong and broadband absorption in visible region (from 450-750 nm). This strategy was demonstrated by preparation of (BODIPY)2-diiodo-aza-BODIPY triad (B-2) and (carbazole-styryl BODIPY)2-diiodo-aza-BODIPY triad (B-3), in which the energy donor (BODIPY or styryl-BODIPY) and the energy acceptor (aza-BODIPY, also as the spin converter) parts were connected by click chemistry. Both the energy donors and the energy acceptors show strong absorption in the visible spectral region, but at different wavelengths, therefore the triads show broadband absorption in visible spectra region, e.g. the two major absorption bands of B-3 are located at 593 nm and 683 nm, with ε up to 220 000 M-1 cm-1 and 81 000 M-1 cm-1, respectively. For comparison, a reference compound with only diiodo-aza-BODIPY as the light-harvesting unit was prepared (B-1), which shows only one major absorption band in visible spectral region. Fluorescence studies indicated intramolecular energy transfer for these BODIPY hybrids, a conclusion which is supported by the femtosecond time-resolved transient absorption spectroscopy. Nanosecond transient absorption spectra show that triplet excited states of the dyad and the triad are localized on the iodo-aza-BODIPY part. The compounds were used as triplet photosensitizers for singlet oxygen (1O2) mediated photooxidation of 1,5-dihydroxylnaphthalene and the photosensitizing ability of the new triplet photosensitizers are more efficient than the mono-chromophore based triplet photosensitizers. The molecular design rationale of these RET-enhanced multi-chromophore triplet photosensitizer is useful for development of efficient triplet photosensitizers and for their applications in photocatalysis, photodynamic therapy, photovoltaics and upconversion.

KSRP/FUBP2 is a binding protein of GO-Y086, a cytotoxic curcumin analogue

Bis(arylmethylidene)acetone derivatives are an important class of curcumin analogues that exhibit various biological and pharmacological activities. We herein report that GO-Y086, a biotinylated bis(arylmethylidene)acetone, inhibits cancer cell growth. We also show that GO-Y086 specifically interacts with the nuclear protein KSRP/FUBP2 by covalent modification. GO-Y086 markedly suppresses the expression of the c-Myc protein, which plays an important role in cellular proliferation and whose expression is regulated by KSRP/FUBP2.

Histone deacetylase inhibitors through click chemistry

Histone deacetylase inhibitors (HDACi) are a relatively new class of chemotherapy agents. Herein, we report a click-chemistry based approach to the synthesis of HDACi. Fourteen agents were synthesized from the combination of two alkyne and seven azido pre

Applications of solid supported azide anion: A one-pot, two-step preparation of functionalized 1,2,3-triazoles

Functionalized 1,2,3-triazoles were prepared in a one-pot, two-step synthesis from alkyl halides and alkynes using a polymer supported azide. Two different base resins were examined. The chemistry is suitable for the preparation of combinatorial libraries.