24345-74-2

Usage

Chemical Properties

Clear Colorless Oil

Uses

Multifunctional alkylating agent

InChI:InChI=1/C4H8N6O/c5-9-7-1-3-11-4-2-8-10-6/h1-4H2

Upstream product

• 7460-82-4 diethylene glycol ditosylate 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 5414-19-7 1,1'-oxybis(2-bromo-ethane) 
• 34604-52-9 diethylene glycol dimesylate 

Downstream Products

• 2752-17-2 2,2'-diaminodiethyl ether 
• 1204387-19-8 C₄₀H₄₂N₈O₄ 
• 1204387-14-3 C₄₀H₄₂N₈O₄ 
• 1350896-45-5 C₂₄H₂₈N₆O₃ 
• 1281972-09-5 C₁₁H₁₆N₂O₂ 
• 1424069-81-7 4-phenyl-1-(2-(2-(4-phenyl-1,2,3-triazol-1-yl)ethoxy)ethyl)-1,2,3-triazole 
• 464190-91-8 2-aminoethyl 2’-azidoethyl ether 

Relevant academic research and scientific papers

Regioselective formation of diazafulleroids bridged by glycol diacetate and glycol chains

Five diazafulleroids with neighbouring double 5, 6-insertion were regioselectivity synthesized by the reactions of C60 with ethylene, diethylene, triethylene glycol di(2-azideacetates) and diethyline, triethylene glycol diazides in refluxing chlorobenzene.

Chemical Promiscuity of Non-Macrocyclic Multidentate Chelating Ligands for Radiometal Ions: H4neunpa-NH2vs H4noneunpa

A comparative investigation of two structurally related potentially nonadentate chelating ligands, H4neunpa-NH2 and H4noneunpa, has been undertaken to examine the influence of bifunctionalization on their coordination chemistry and metal ion selectivity. Significantly improved synthetic routes for each compound have been developed, employing straightforward high-yielding strategies. Radiolabeling studies with [44Sc]Sc3+, [111In]In3+, [177Lu]Lu3+, and [225Ac]Ac3+ revealed a sharp contrast between the affinity of each chelator for large radiometal ions. H4noneunpa demonstrated highly effective coordination of [177Lu]Lu3+ and [225Ac]Ac3+ achieving quantitative radiochemical yields (>98%) at ligand concentrations of 10-6 M (room temperature (RT), 10 min), with excellent stability when challenged in human serum, while H4neunpa-NH2 was unable to complex either metal ion effectively. Nuclear magnetic resonance (NMR) spectroscopy was employed to explore the coordination chemistry of each chelating ligand with nonradioactive metal ions, spanning a range of ionic radii and coordination numbers. A comprehensive conformational analysis of each metal complex was undertaken using density functional theory (DFT) calculations to explore the coordination geometries and explain the discrepancy in binding characteristics. Theoretical simulations revealed notable differences in the coordination geometry and apparent denticity of each ligand, which together account for the observed selectivity in metal binding and have important implications for the future design of complexes based upon this framework to target large radiometal ion coordination.

A novel graphite-like stacking structure in a discrete molecule and its molecular recognition behavior

A graphite-like stacking structure was nicely reproduced in a discrete molecule that was prepared by 2+2 macrocyclic Schiff base formation. In the crystal structure, two hexabenzocoronene planes are closely stacked with displacement, yielding the intramolecular stacking structure similar to an AB- or ABC-stacking pattern in natural graphite. This molecule showed a recognition ability toward electron-deficient aromatic molecules in solution.

Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens

A new family of bipodal anion transporters based on chalcogen-containing scaffolds has been designed and synthesized. Though structurally related to the well-studied tripodal anionophores, these molecules are simpler with only two anion-binding sites. However, the activities remain high. Anion transport could be facilitated by the new transporter at an exceptionally low loading of transporter/lipid ratio of 1:500000. This impressive efficiency is comparable with the most active one from the tren-based tripodal series. To investigate influences from different scaffolds and substituent groups, lipophilicity, anion-binding property, and transport activity of each molecule were studied. It was found that the bridge atom has a major impact on transport activities mainly as a result of anion-binding differences. The results also suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities. Anion transporters based on chalcogen-containing scaffolds have been designed and synthesized. Their lipophilicities, anion binding properties, and transport activities were investigated in detail. The results suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities.

A Fluorescent and Switchable Rotaxane Dual Organocatalyst

Rotaxane organocatalysis presents a new direction toward controlled one-pot catalytic reactions. By combining molecular switches and catalysts, fluorescence and pH-responsive switching along with the exclusive selectivity of dual catalytic reactions are d

Visible light-activatable cyclodextrin-conjugates for the efficient delivery of nitric oxide with fluorescent reporter and their inclusion complexes with betaxolol

This contribution reports the design, synthesis, photochemical properties and drug inclusion capability of two novel β-cyclodextrin (βCD) conjugates, βCD-NBFNO1 and βCD-NBFNO2, covalently integrating an N-nitroso amino-nitro-benzofurazan in the primary and secondary hydroxyl rims of the βCD scaffold, respectively through flexible spacers of different length. Both βCD conjugates are water-soluble and release nitric oxide (NO) under the input of either blue or green light, with quantum yields ΦNO (blue) = 0.13, 0.31 and ΦNO (green) = 0.007, 0.013 respectively, the former representing the largest values ever reported for nonmetal-containing NO donors activatable by visible light. The good contrast between the fluorescence green emission of the chromogenic moiety after and before the NO release permits the easy and in real-time quantification of the amount of NO generated, without the addition of external fluorescent agents. Despite the presence of the appendages, these βCD derivatives are also able to complex betaxolol, a β-blocker drug widely used for the reduction of the intraocular pressure, with binding constants Kb = 500 ± 50 and 1100 ± 100 M-1, respectively, without affecting the photochemical performances. In view of the well-known vasodilator properties of NO, the present βCD derivatives represent intriguing candidates for biopharmaceutical research studies addressed to combined therapeutic ocular applications.

Thermal response of a PVCL-HA conjugate

The synthesis and self-assembling of a thermoresponsive conjugate of hyaluronic acid (HA) and poly(N-vinylcaprolactam) (PVCL) is reported. Both polymers were end functionalized: HA via reductive amination, thereby introducing an azide endgroup to the chain end, and PVCL via thioetherification to introduce a propargyl group. The two were coupled with a copper assisted "click" reaction into a bioconjugate composed of HA blocks with the molar mass 3,600 g mol-1 (1618 saccharide units) and PVCL blocks of 3,500 g mol-1 (μ25 repeating units). The cloud point temperature measured by transmittance was 50-51 °C in water. The calorimetrically observed phase transition temperature of PVCL in the conjugate increased by 2 °C to 47.7 °C, whereas the enthalpy of the phase transition was unaffected by the conjugation. HA-PVCL conjugate self-assembles in water upon heating into monodisperse, colloidally stable, hollow spherical particles whose size may be tuned with the heating rate of the solution. Slow and fast heating resulted in vesicles with the hydrodynamic radii of 443 or 275 nm, respectively. The heating rate did not, however, affect the cloud point. Salt did not noticeably affect the size of the polymer particles, presumably because of interactions between the HA and PVCL blocks.

Catalytic Synthesis of PEGylated EGCG Conjugates that Disaggregate Alzheimer's Tau

The naturally occurring flavonoid ( )-epigallocatechin gallate (EGCG) is a potent disaggregant of tau fibrils. Guided by the recent cryo-electron microscopy (cryoEM) structure of EGCG bound to fibrils of tau derived from an Alzheimer s brain donor, methods to site-specifically modify the EGCG D-ring with aminoPEGylated linkers are reported. The resultant molecules inhibit tau fibril seeding by Alzheimer s brain extracts. Formulations of aminoPEGylated EGCG conjugated to the (quasi)-brain-penetrant nanoparticle Ferumoxytol inhibit seeding by AD-tau with linker length affecting activity. The protecting groupfree catalytic cycloaddition of amino azides to mono-propargylated EGCG described here provides a blueprint for access to stable nanoparticulate forms of EGCG potentially useful as therapeutics to eliminate Alzheimer s-related tau tangles.

Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry

Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.

Electrochemical CO2 Reduction-The Effect of Chalcogenide Exchange in Ni-Isocyclam Complexes

Among the numerous homogeneous electrochemical CO2 reduction catalysts, [Ni(cyclam)]2+ is known as one of the most potent catalysts. Likewise, [Ni(isocyclam)]2+ was reported to enable electrochemical CO2 conversion but has received significantly less attention. However, for both catalysts, a purposeful substitution of a single nitrogen donor group by chalcogen atoms was never reported. In this work, we report a series of isocyclam-based Ni complexes with {ON3}, {SN3}, {SeN3}, and {N4} moieties and investigated the influence of nitrogen/chalcogen substitution on electrochemical CO2 reduction. While [Ni(isocyclam)]2+ showed the highest selectivity toward CO2 reduction within this series with a Faradaic efficiency of 86% for the generation of CO at an overpotential of-1.20 V and acts as a homogeneous catalyst, the O-and S-containing Ni complexes revealed comparable catalytic activities at ca. 0.3 V milder overpotential but tend to form deposits on the electrode, acting as precursors for a heterogeneous catalysis. Moreover, the heterogeneous species generated from the O-and S-containing complexes enable a catalytic hydride transfer to acetonitrile, resulting in the generation of acetaldehyde. The incorporation of selenium, however, resulted in loss of CO2 reduction activity, mainly leading to hydrogen generation that is also catalyzed by a heterogeneous electrodeposit.