Acridines

Acridine (dibenzo(b,e)pyridine; 2,3,5,6-dibenzopyridine; 2,3-benzoquinoline; 10-azaanthracene) alkaloids are flat (planar) aromatic, hydrophobic nitrogen heterocycles, structurally related to anthracene with one of the central CH groups replaced by nitrogen. Acridine derivatives have a long history, beginning with antimicrobial activity that was reported by Ehrlich and Benda in 1912, and exhibit several drug properties, such as anticancer, antibiotic anti-AchE, antiprion, anticiceptive, antileukemia, antimalarial, antipsychotic, antidepressant, antidimentia, antinociceptive, and telomerase inhibition. Their hydrophobicity allows them to diffuse into the cell membrane and complex with (intercalate) DNA and RNA; giving them their drug properties as well as causing fluorescence that can be used to study cellular processes like cell cycle determination, stain nucleic acids, and flow cytometry. 9-Aminoacridine hydrochloride monohydrate is a mutagen, but appropriately substituted 9-arylaminoacridine anticancer drugs act via interference with the mammalian topoisomerase II enzyme. The presence of a halogen allows these reagents to be used as substrates in various coupling reactions, including Suzuki-Miyaura cross-coupling reactions. Sigma-Aldrich offers several acridine derivatives to facilitate drug discovery.

Product #

Image

Description

Molecular Formula

Add to Cart

722502 9-Bromoacridine 97% C13H8BrN
159425 9-Chloroacridine 97% C13H8ClN
145688 6,9-Dichloro-2-methoxyacridine 97% C14H9Cl2NO
CDS000473 Coriphosphine O AldrichCPR C16H18ClN3
672548 6-Chloro-2-methoxy-9-phenoxyacridine 98% C20H14ClNO2