20149-91-1

Upstream product

• 82-45-1 1-amino-9,10-anthracenedione 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1093274-89-5 C₂₆H₁₈N₃O₂⁽¹⁺⁾*Cl^(1-) 
• 112322-20-0 N-o-tolyl-glycine-(9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 75534-84-8 N-phenyl-glycine-(9,10-dioxo-9,10-dihydro-[1]anthrylamide) 

Relevant academic research and scientific papers

Single crystal X-ray structure and optical properties of anthraquinone-based dyes

This study focuses on the preparation, single crystal X-ray diffraction, characterization, and optical properties of some anthraquinone-based dyes. The anthraquinone-based antimicrobial dye N-{2-[(9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-2-oxoethyl}-N,N-dimethylbutan-1-aminium chloride monohydrate (III) was obtained from 1-aminoanthraquinone (I) via 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide (II) using known preparation and characterization methods. Single crystal X-ray diffraction analysis of III revealed a monoclinic system, space group P21/n, Z = 4. Photoluminescence properties of anthraquinone dyes I-III were also investigated. These dyes gave an intense emission (λmax = 341 nm) upon the irradiation by UV light and showed photoluminescence quantum yields of 73 %, 66 %, and 61 % with long excited-state lifetimes of 6.87 ns, 6.14 ns, and 5.69 ns, respectively. These anthraquinone dyes are of interest as an organic light emitting material for electroluminescent devices.

Efficiently functionalized oxacalix[4]arenes: Synthesis, characterization and exploration of their biological profile as novel HDAC inhibitors

A series of novel substituted oxacalix[4]arene has been synthesized and explored for their biological profile by evaluating anticancer, antifungal and antibacterial properties. The derivatives have been characterized by various spectroscopic techniques su

Following the solvent directly during ultrafast excited state proton transfer

Excited state intramolecular proton transfer in 1-chloroacetylaminoanthraquinone is investigated from the perspective of the solvent. Using a new two-dimensional nonlinear optical spectroscopy the solvent response is probed directly as the proton transfer takes place. The measurements indicate that solvent reorganization controls the proton transfer in acetonitrile by dynamically shifting the position of equilibrium in the excited state, even on subpicosecond time scales. Copyright

Calix[4]pyrrole virtuous sensor: a selective and sensitive recognition for Pb(II) ions by spectroscopic and computational study

A novel supramolecular sensor derived from calix[4]pyrrole system i.e. calix[4]pyrrole bearing aminoanthraquinone derivative (CAAQ) have been designed and synthesized. The complexation behavior of metal cations [Ag(I), Ba(II), Ca(II), Ni(II), Co(II), Fe(I

A highly selective anthraquinone appended oxacalixarene receptor for fluorescent ICT sensing of F? ions: an experimental and computational study

Abstract: A new anthraquinone appended oxacalix[4]arene (DAQOC) has been synthesized and characterized by different 1H NMR, IR, ESI-MS and 13C NMR spectroscopic techniques. This compound was explored for its sensing abilities towards various anions. DAQOC showed selective anion sensing behaviour towards F? ions which was supported by absorption as well as emission studies. Among other anions, only in the presence of F? ions, a quenching in the fluorescence emission of over 79% was observed due to changes in the intermolecular charge transfer (ICT) process. DAQOC exhibited high selectivity and good sensitivity toward F? ions in the presence of competing ions and the detection limit was found to be 1.23 μM. 1H NMR titration displays that the peak corresponding to –NH protons (at 12.91 ppm) disappears upon interaction with F?, suggesting that the sensing mechanism follows the deprotonation route. The geometrical features of F? bound oxacalixarene species were modelled by the Density Functional Theory (DFT) and NCIPlot calculations. The findings suggested that the appended substituents including nitro groups and anthraquinone can make the calix[4]arene ring electron deficient and thereby more susceptible for F? ions. Moreover, this present chemosensor has been applied for recognition of F? ions from waste water samples which is of direct practical relevance. Graphic abstract: A new anthraquinone appended oxacalix[4]arene has been explored for its sensing abilities towards F? by absorption and emission studies. An intermolecular charge transfer mechanism has been attributed due to the deprotonation of N–H groups in DAQOC. DAQOC-F? complex is modelled by the Density Functional Theory and NCIPlot calculations.[Figure not available: see fulltext.]

Preclinical evaluation of DO3A-Act-AQ: A polyazamacrocyclic monomeric anthraquinone derivative as a theranostic agent

An anthraquinone conjugated macrocyclic chelating agent, 2,2′,2″-(10-(2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino) -2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid or DO3A-Act-AQ, was synthesized by reacting trisubstituted cyclen (DO3A) with 2-chloro-N-(9,10-dioxo-9,10-dihydro-anthracen-1-yl)-acetamide and radiolabeled with 68GaCl3 in 84% efficiency and a specific activity of 4.62 MBq/nmol. The IC50 value for BMG-1 cells was 0.1 mM, while the same concentration of DO3A-Act-AQ rendered no significant toxicity in HEK cells. The exposure of BMG-1 cells with 0.1 mM DO3A-Act-AQ displayed a time-dependent increase in apoptosis (40.7% at 4 h and 53% at 24 h), and the effect was 2.8- and 3.6-fold % higher as seen in HEK cells. An increase in S-phase cell population suggested S-phase arrest concomitant with induction of apoptosis in BMG-1 cells reaching to 4.5 times after 24 h with respect to control cells. DNA binding studies on CT-DNA (calf thymus) revealed a quenching pattern in the presence of DO3A-Act-AQ (10-70 μM), and the Stern-Volmer quenching constant was 2.4157 × 106 L mol-1, indicative of strong binding with ds-DNA. A decrease in the positive and negative bands of CT-DNA was seen at 278 nm and 240 nm, respectively, on addition of 0.05 mM of DO3A-Act-AQ in CD studies. 68Ga-DO3A-Act-AQ was stable in vitro in both PBS and human serum for at least 2 h. The in vivo blood kinetics study performed on normal rabbits indicated fast clearance with t1/2(F) = 40 ± 0.3 min and t1/2(S) = 3 h 30 min ± 0.1 min. Ex vivo biodistribution analysis displayed a favorable tumor-to-muscle ratio of 8.4 after 2 h in athymic nude mice xenografted with BMG-1 cells, suggesting the specificity of 68Ga-DO3A-Act-AQ toward tumors.

Chromofluorogenic naphthoquinolinedione-based probes for sensitive detection and removal of Hg2+ in aqueous solutions

Mercury ions are an industrial and environmental toxin that need to be monitored and regulated in aqueous samples. We prepared six probes (1–6) using a naphthoquinolinedione ring as a fluorophore platform that contains different substituents on the quinolone ring. All probes showed abilities to selectively bind Hg2+, but their sensitivity to the detection of this metal ion significantly varied depending on the substituent pattern. Among these probes, probe 5 with Br and CN substituents on the quinolone ring was most effective for the sensitive detection of Hg2+ in aqueous solutions. This probe showed a naked-eye color change from yellow to purple upon binding to Hg2+. A ratio-metric method using UV–visible absorption data gave a limit of detection (LOD) of 20 nM, while the fluorescence-based result yielded an LOD of 0.047 pM. When bio-samples such as human urine and serum were used as media, the fluorescence-based LOD of this probe for Hg2+ detection increased to 50 nM. Probe 5 was also effective at detecting methylmercury, an organic mercury species, dissolved in drainage water or urine. Based on the results of DLS, FE-SEM, and DFT calculations, the probe appeared to form large aggregates and undergo photo-induced electron transfer (PET) upon Hg2+ binding, both of which are responsible for the probe fluorescence quenching. Probe 5 also showed the ability to sense Hg2+ within three different types of human cells: Brain cells (U87MG), Hela cells and skin cancer cells (SK-MEL28). Furthermore, this probe holds significant potential for on-site applications since various solid supports such as silica gel, filter papers and TLC plates were effectively used for sensitive and selective Hg2+ sensing, following probe coating/adsorption.

In Silico Studies and Design of Scrupulous Novel Sensor for Nitro Aromatics Compounds and Metal Ions Detection

A Novel calix[4]pyrrole system bearing carboxylic acid functionality [ABuCP] has been synthesized and its interaction towards various nitroaromatics compounds [NACs] were investigated. ABuCP showed significant color change with 1,3-dinitro benzene (1,3-DNB) in comparison to the solution of other nitroaromatic compounds such as 2,3-dinitro toluene (2,3-DNT), 2,4-dinitro toluene (2,4-DNT), 2,6-dinitro toluene (2,6-DNT), 4-NBB (4-nitrobenzyl bromide) and 4-nitro toluene (4-NT). The ABuCP-1,3-DNB complex produces a red shift in absorption spectra based on charge transfer mediated recognition. Additionally, the density functional theory calculation confirmed the possible mechanism for the binding of 1,3-DNB as a guest is well supported by the calculation of other parameters such as hardness, stabilization energy, softness, electrophilicity index and chemical potential. The TDDFT calculation facilitates the understanding of the proper binding mechanism in reference to experimental results. Additionally we have also developed its derivative which acts as a new fluorescent sensor which can selectively recognize Sr(II) ions. In this view its aminoanthraquinone derivative of calix[4]pyrrole i.e. ABuCPTAA is synthesized which also results in generation of high fluorescence capability sensor.

Anthraquinone-based electroactive ionic species as stable multi-redox anode active materials for high-performance nonaqueous redox flow batteries

Anthraquinone (AQ)-based materials are promising active materials for aqueous redox flow batteries (ARFBs) owing to their fast kinetics and reversible two-electron redox reactions, but their application in non-aqueous RFBs (NARFBs) is limited by the low solubility and inferior stability of the charged species in aprotic solvents. Here, three AQ-based electroactive ionic species are purposely designed for NARFBs by incorporating the acetamide group and tetraalkylammonium ionic group into the anthraquinone structure and pairing with hydrophobic counter anions. Both experimental and theoretical calculation results show improved solubility and stability. A two-electron transfer redox flow battery with a mixed-reactant electrolyte delivers impressive cycling performance with an average coulombic efficiency of 96.8%, energy efficiency of 82.4%, and overall discharge capacity retention of 86.0% over 200 cycles (99.93% capacity retention per cycle) at 10 mA cm?2. Furthermore, the battery exhibits robust rate capability to bear the current fluctuation.

Dual targeting of cholinesterase and amyloid beta with pyridinium/isoquinolium derivatives

With the surge in the cases of Alzheimer's disease (AD) over the years, several targets have been explored to curb the disease. Cholinesterases, namely acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), remain to be the available targets that are amendable to currently approved treatments. In this study, a series of novel compounds based on tramiprosate, a highly specific amyloid beta (Aβ) inhibitor, was designed to inhibit AChE, BuChE, and Aβ aggregation. In particular, the addition of a pyridinium/isoquinolinium ring to the tramiprosate moiety (to give compounds 3a–j) led to an increase in the binding affinity for the catalytic active site of cholinesterase, which was hampered by the presence of sulfonic acid. Exclusion of the sulfonic acid moiety led to a novel but effective class of cholinesterase inhibitors (9a–w). in vitro Aβ aggregation inhibition assay indicated that compounds 3a–j, 9e–f, 9i–l, 9q, 9r, 9u–w, and 12 could inhibit over 10% Aβ aggregation at 1 mM concentration. Cholinesterase inhibition assay suggested that compounds 9g, 9h, 9o, and 9q–t exhibit over 70% inhibition on both AChE and BuChE at a concentration of 100 μM. Amongst the designed molecules, compound 9r (ca 18% at 1 mM) showed comparable inhibitory effect on the inhibition of Aβ aggregation with tramiprosate (ca 20% at 1 mM), along with impressive cholinesterase inhibitory potential (AChE IC50 = 13 μM and BuChE IC50 = 12 μM), acceptable toxicity and ability to pass through blood brain barrier, which could be used to ameliorate the phenotypes of AD in preclinical models.