6564-45-0

Upstream product

• 1758-68-5 1,2-diamino-9,10-anthraquinone 
• 104-87-0 4-methyl-benzaldehyde 

Relevant academic research and scientific papers

One-pot protocol for J-aggregated anthraimidazolediones catalyzed by phosphotungstic acid in PEG-400 under aerobic condition

A precise and productive one pot green protocol has been developed for the chemoselective synthesis of anthra[1,2-d]imidazole-6,11-diones using phosphotungstic acid (PTA) as a reusable catalyst on polyethylene glycol-400 (PEG-400) support under aerobic condition. It involves a simple synthetic procedure for a wide range of anthraimidazolediones from 1,2-diaminoanthraquinone and various aldehydes possessing π-enriched aromatic/heteroaromatic rings and lipophilic alkyl chains. In inert atmosphere, the reaction followed a different pathway, yielding a unique naphtho-quinoxaline derivative. Synthesized anthraimidazoledione derivatives had shown different self-aggregation morphologies influenced by the substitution pattern. A nice agreement between crystal packing pattern and photophysical properties with J-aggregation morphology was also observed. Representative derivatives exhibited contrasting fluorescence behaviors in transition from solution state to nanostructured solid state.

Synthesis and evaluation of quinonoid compounds against tumor cell lines

Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 μM for some compounds. The β-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII).

The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-β-lapachone derivatives and β-lapachone-based 1,2,3-triazoles

In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas' disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream trypomastigote forms of the parasite. Compounds 2,2-dimethyl-3-(2,4-dibromophenylamino)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione, IC50/24 h 24.9 ± 7.4 and 4-azido-3-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione with 23.4 ± 3.8 μM showed a trypanosomicidal activity higher than benznidazole. These results demonstrate the potential of naphthoquinone derivatives as novel structures for the development of alternative drugs for Chagas' disease.

Synthesis, cytotoxicity and human telomerase inhibition activities of a series of 1,2-heteroannelated anthraquinones and anthra[ 1,2-d]imidazole-6,11 -dione homologues

A series of 1,2-heteroannelated anthraquinones and anthra[1,2-d]imidazole- 6,11-dione tetracyclic analogues with different side chain were prepared using an various synthetic route via acylation, cyclization, condensation, and intramolecular heterocyclization. Tetracyclic system containing alkyl and aryl, aromatic and heterocyclic, linear and cyclic, polar and apolar, and basic and acids residues were incorporated. They were evaluated for their effects on telomerase activity, hTERT expression, cell proliferations, and in vitro cytotoxicity against NCI's 60 cell line human tumor screen. Compounds 4, 11, 12, 14, 15, 16, 17, 19, 20, 23, 25, and 26 were selected by the NCI for one dose screening program and further studies on 4, 23 and 25 where the curves cross these lines represent the interpolated values to cause 50% growth inhibition (GI50), total growth inhibition (TGI) and 50% cell killing (LC 50). respectively. Further studies did not reveal any compound that showed potent and significant on telomerase inhibitory activity and hTERT repressing ability. Comparative testing of these compounds in the NCI's screen revealed varying levels of potency and differential cytotoxicity, apparently related to the unsaturation levels in and substitution patterns on the core ring system. It appeared that addition of a fourth planar aromatic system to a tricyclic chromophore might enhances potent cytotoxic agents, at a level equivalent to a second side chain in one of the tricyclic series. Although the exact mechanism of how this pharmacophore contributes to its activity is still unclear, however, the group in the extended arm of the tetracyclic system might contribute to proper binding to the residues within the grove of G-quadruplex structure.

HETEROANNELATED ANTHRAQUINONE DERIVATIVES AND THE SYNTHESIS METHOD THEREOF

A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I): wherein R1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH2)nX, a straight (CH2)n alkyl group, a (CH2)n alkoxyl group, a branched (CH2)n alkyl group, a C3?C12nephthenic group, and a C3?C12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C1?C8 alkyl group with a double-bond, a C1?C8 alkoxyl group with a double-bond, a branched C1?C8 alkyl group with a double-bond and a C3?C8 nephthenic group with a double-bond, and iv) a fourth substituent of a C5?C12 heterocyclic group.