143210-98-4

Upstream product

• 79-04-9 chloroacetyl chloride 
• 117-79-3 2-aminoanthraquinone 

Downstream Products

• 143211-08-9 1-(anthraquinon-2-yl)-3-carboethoxy-2,5-pyrrolidindione 
• 143211-04-5 1-(anthraquinon-2-yl)-5-benzylidene-1,3-thiazolidin-2,4-dione 

Relevant academic research and scientific papers

Confined Singlet Oxygen in Mesoporous Silica Nanoparticles: Selective Photochemical Oxidation of Small Molecules in Living Cells

(Chemical Equation Presented) Chemical conversion of specific bioactive molecules by external stimuli in living cells is a powerful noninvasive tool for clarification of biomolecular interactions and to control cellular functions. However, in chaotic biological environments, it has been difficult to induce arbitrary photochemical reactions on specific molecules because of their poor molecular selectivity. Here we report a selective and nontoxic photochemical reaction system utilizing photoactivated mesoporous silica nanoparticles to control biological functions. Methylene blue modification within nanoparticle pores for photosensitization produced singlet oxygen confined to the pore that could mediate selective oxidation of small molecules without any damage to living cells. This intracellular photochemical system produced bioactive molecules in situ and remotely controlled the cell cycle phase. We also confirmed that this photoreaction could be applied to control cell cycle phase in tumor tissue transplanted in mice. The cell cycle phase in the cells in mice, to which our system was administered, was arrested at the G2/M phase upon photoirradiation. We demonstrate a simple and promising method for the exogenous conversion of an intracellular biomolecule to another functional compound.

Synthesis, optical and electrochemical properties of new receptors and sensors containing anthraquinone and benzimidazole units

Novel anion receptors and sensors, HBIMANQ and BIMANQ fabricated from the imidazolole unit and anthraquinone moieties were synthesized. 1H NMR spectroscopy and UV-vis titrations in DMSO-d6 and DMSO, respectively, showed that both receptors underwent deprotonation at the NH- moiety of the amide-anthraquinone unit in the presence of basic anions such as F- and AcO-. These phenomena gave a dramatic color change due to charge transfer transition corresponding to the shift of λmax from 371 nm to 489 nm. Redox chemistry of HBIMANQ and BIMANQ in the presence of anions (F-, Cl-, AcO-, BzO-, and H2PO4-) using cyclic voltammetry showed the different CV responses upon addition of various anions. In the case of HBIMANQ with various anions, the CV changes are dependent on the basic strength of anions in order of F->AcO-, BzO->H2PO4->Cl-, Br-. Interestingly, the CV responses of BIMANQ with H2PO4- exhibited the most significant changes. BIMANQ, thus, has an excellent electrochemical selectivity toward H2PO4-.

Synthesis and characterization of new water soluble 9,10-anthraquinonе and evaluation of its antimicrobial activity

The synthesis and characterization of a new cationic anthraquinone derivative (S3) soluble in water has been described. Its absorption characteristics in aqueous and N,N-dimethylformamide solutions have been determined. Аntimicrobial activity of the compound S3 was tested in vitro towards eight pathogenic bacteria and two yeasts strains. The results obtained suggest that the newly synthesized compound is effective in treating the relevant pathogens and is suitable in designing new effective antimicrobial preparations. Antimicrobial activity and release of S3 after its deposition on cotton fabric and incorporation into thin polylactid film have also been investigated.

Novel anthraquinone derivative, and synthesis method and application thereof

The invention discloses a novel anthraquinone derivative, and a synthesis method and an application thereof, and belongs to the field of compounds. The method comprises the steps: step 1, carrying outa reaction on 2-aminoanthraquinone with chloroacetyl chloride in the presence of an alkaline reagent to obtain a compound II; and step 2, carrying out a reaction on the compound II with m-phenylenediamine in the presence of an alkaline reagent to obtain a compound III. The preparation method of the anthraquinone derivative provided by the invention is simple, and the anthraquinone derivative hashigh sensitivity as a fluorescent chemical sensor.

Inducing apoptosis through upregulation of p53: structure–activity exploration of anthraquinone analogs

We previously reported a series of p53-elevating anthraquinone compounds with considerable cytotoxicity for acute lymphoblastic leukemia (ALL) cells. To further develop this class of compounds, we examined the effect of a few key structural features on the anticancer structure–activity relationship (SAR) in ALL cells. The active analogs showed comparable cytotoxicity and upregulation of p53 but did not induce significant downregulation of MDM2 as seen with the lead compound AQ-101, indicating the importance of the anthraquinone core scaffold for MDM2 regulation. The result from the current study not only contributes to the SAR framework of these anthraquinone derivatives but also opens up new chemical space for further optimization work.

Photoreleasable Protecting Groups Triggered by Sequential Two-Photon Absorption of Visible Light: Release of Carboxylic Acids from a Linked Anthraquinone- N -Alkylpicolinium Ester Molecule

A photoreleasable protecting group activated by sequential absorption of two visible photons is designed, synthesized, and tested. Specifically, an anthraquinone-based chromophore is covalently attached to an N-alkylpicolinium ester. Photolysis of this linked system results in the clean release of a corresponding carboxylic acid. Through product analysis, laser flash photolysis, and steady-state UV-vis spectroscopy, it is demonstrated that carboxylate ion release is affected by sequential absorption of two photons. The initial photochemical step results in reduction of an anthraquinone chromophore to the corresponding hydroquinone. The latter either reacts with O2 to regenerate the starting material, or absorption of a second photon causes an electron transfer to the picolinium group triggering C-O bond scission and release of the carboxylate.

Synthesis and biological activity of some heterocyclic systems containing anthraquinone

2-Aminoanthraquinone (1) was reacted with ethyl chloroformate to afford 2. The reaction between carbamate 2 and hydrazine hydrate gave semicarbazide 3, which on treatment with benzoic acid, phenyl isothiocyanate and carbondisulfide/potassium hydroxide furnished oxadiazoles 4, 6 and triazole 5, respectively. Also, treatment of 1 with chloroacetyl chloride gave chloroacetyl derivative 8. The reaction of glycolic acid, thioglycolic acid, diethylmalonate and malononitrile with 8 has been investigated. Compound 8 was treated with potassium thiocyanate to give 12, which was cyclized to 13a, while the reaction between 8 and potassium cyanate gave 13b directly. The structures of hitherto unknown compounds were confirmed by analytical and spectral methods. Some of the synthesized compounds were screened to test their antibacterial and antifungal properties.