70945-59-4

Usage

Chemical structure

A complex chemical compound with a polyaromatic structure containing anthracene and piperidine moieties.

Functional groups

Contains a quinone-hydroquinone structure with two hydroxyl groups at positions 1 and 4, and two piperidine-ethylamine groups at positions 5 and 8 of the anthracene core.

Potential applications

May have potential applications in medicinal chemistry, specifically in the development of antitumor or antibacterial agents, as well as in organic electronic materials.

Unique properties

Its unique structure and properties make it of interest for further research and potential applications in various fields.

Molecular weight

Approximately 482.6 g/mol

Appearance

Likely to be a solid, possibly with a crystalline structure.

Solubility

Solubility in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO) is expected, but specific solubility data is not provided.

Stability

Stability under normal conditions is expected, but specific stability data is not provided.

Synthesis

The synthesis of 1,4-dihydroxy-5,8-bis{[2-(piperidin-1-yl)ethyl]amino}anthracene-9,10-dione likely involves multiple steps, including the formation of the anthracene core, introduction of the hydroxyl groups, and attachment of the piperidine-ethylamine groups.

Upstream product

• 27578-60-5 1-(2-aminoethyl)piperidine 
• 131401-54-2 1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione 

Relevant academic research and scientific papers

Synthesis of DNA-directed pyrrolidinyl and piperidinyl confined alkylating chloroalkylaminoanthraquinones: Potential for development of tumor-selective N-oxides

A novel series of 1,4-disubstituted chloroethylaminoanthraquinones, containing alkylating chloroethylamino functionalities as part of a rigid piperidinyl or pyrrolidinyl ring-system, have been prepared. The target compounds were prepared by ipso-displacement of halides of various anthraquinone chromophores by either hydroxylated or chlorinated piperidinyl- or pyrrolidinyl-alkylamino side chains. The chloroethylaminoanthraquinones were shown to alkylate guanine residues of linearized pBR322 (1-20 μM), and two symmetrically 1,4-disubstituted anthraquinones (compounds 14 and 15) were shown to interstrand cross-link DNA in the low nM range. Several 1,4-disubstituted chloroethylaminoanthraquinones were potently cytotoxic (IC50 values: ≤40 nM) in human ovarian cancer A2780 cells. Two agents (compounds 18 and 19) exhibited mean GI50 values of 96 nM and 182 nM, respectively, in the NCI human tumor cell line panel. Derivatization of the potent DNA cross-linking agent 15 to an N-oxide resulted in loss of the DNA unwinding, DNA interstrand cross-linking and cytotoxic activity of the parent molecule.

ANTHARQUINONE COMPOUNDS AS ANTI CANCER COMPOUNDS

Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R1 to R4 are each selected from the group consisting of H, C1-4 alkyl, X1, -NHR0N (R5)2 in which R0 is a C1-12 alkanediyl and each R5 is H or optionally substituted C1-4 alkyl, and a group of formula (II) in which at least one of R6,R7 and R8 is selected from X2 , and X2 substituted C1-4 alkyl and any others are H or C1-4 alkyl; R9 is selected from H, C1-4 alkyl, X2 and X2 substituted C1-4 alkyl; m is 0 or 1; n is 1 or 2; X1 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; and X2 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R1 to R4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.