6470-90-2

Basic information

• Product Name: N,N'-(9,10-dihydro-9,10-dioxoanthracene-2,6-diyl)bisbenzamide
• Synonyms: N,N'-(9,10-dihydro-9,10-dioxoanthracene-2,6-diyl)bisbenzamide;2,6-dibenzamidoanthraquinone;EINECS 229-300-1;2,6-Bis(benzoylamino)-9,10-anthraquinone;2,6-Bis(benzoylamino)anthraquinone
• CAS NO: 6470-90-2
• Molecular Formula: C₂₈H₁₈N₂O₄
• Molecular Weight: 446.45352
• EINECS: 229-300-1
• Mol File: 6470-90-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 561.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.409±0.06 g/cm3(Predicted)
• PKA: 12.11±0.20(Predicted)
• CAS DataBase Reference: N,N'-(9,10-dihydro-9,10-dioxoanthracene-2,6-diyl)bisbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-(9,10-dihydro-9,10-dioxoanthracene-2,6-diyl)bisbenzamide(6470-90-2)
• EPA Substance Registry System: N,N'-(9,10-dihydro-9,10-dioxoanthracene-2,6-diyl)bisbenzamide(6470-90-2)

Safety Data

• Hazardous Substances Data: 6470-90-2(Hazardous Substances Data)

Upstream product

• 131-14-6 2,6-diamino-9,10-anthraquinone 
• 98-88-4 benzoyl chloride 

Downstream Products

• 66214-41-3 N,N'-(9,10-dioxo-9,10-dihydro-anthracene-2,6-diyl)-bis-benzimidoyl chloride 

Relevant articles and documents

Synthesis and human telomerase inhibition of a series of regioisomeric disubstituted amidoanthraquinones

Telomerase is the enzymatic activity that maintains the ends of eukaryotic chromosomes. Telomerase activity is detected in most tumor cells whereas it is low or undetectable in most normal somatic cells. Expression of the telomerase catalytic component, the human telomerase reverse transcriptase (hTERT), is believed to be controlled primarily at the level of transcription. Because of this selective expression property of telomerase, it has been touted as a specific target for antitumor chemotherapeutics. However, a concern for the applicability of telomerase inhibitors is that they require a long lag time for telomeres to be shortened to critical length before cancer cells stop proliferating. Here we investigate telomerase inhibitory, cytotoxicity and the hTERT repressing effects on a number of synthesized 2,6-diamidoanthraquinones and 1,5-diamidoanthraquinones as compared to their disubstituted homologues. We found that several of the 1,5-diamidoanthraquinones and 2,6- diamidoanthraquinones inhibited telomerase activity effectively with IC 50 at the sub-micro to micro molar range and caused acute cytotoxicity to cancer cells with EC50 similar or better than that of mitoxantrone. Particularly, 2,6-diamidoanthraquinone with 2-ethylaminoacetamido side chains 33, even though not affecting cell proliferation, showed to be endowed with a strong telomerase effect, probably related to a marked stabilization of the G-quadruplex-binding structure. The results suggested that these compounds caused multiple effects to cancer cells. More significantly, they overcome the long lag period problem of classical telomerase inhibitors that they are also potent cytotoxic agents. These results greatly expand the potential of tricyclic anthraquinone pharmacophore in preventive and/or curative therapy.