31293-07-9

Usage

1H-Dibenzo[de,h]quinoline-2,7-dione

+ A naturally occurring alkaloid
+ Heterocyclic compound
+ Found in various plant species (e.g. Indian beech tree and Australian brush cherry)

Ellipticine

+ Has potential anti-tumor properties
+ Demonstrated antitumor and mutagenic effects
+ Studied for its potential as a chemotherapeutic agent
+ Exerts its effects by intercalating into DNA and inhibiting topoisomerase activity
+ Ultimately leads to cell death

Research

+ Ongoing studies on the use of ellipticine in cancer treatment
+ Shows promise as a potential anti-cancer drug

InChI:InChI=1/C16H9NO2/c18-13-8-9-4-3-7-12-14(9)15(17-13)10-5-1-2-6-11(10)16(12)19/h1-8H,(H,17,18)

Upstream product

• 120346-99-8 2-hydroxy-3-ethoxycarbonyl-7H-dibenzoquinolin-7-one 
• 120346-94-3 1-(cyanoethoxycarbonylmethyl)anthraquinone 
• 152027-94-6 1-(carbamoylethoxycarbonylmethyl)anthraquinone 

Relevant academic research and scientific papers

REACTION OF α-HALOGENO- AND α-NITROANTHRAQUINONES WITH THE ANIONS OF CH ACIDS. II. PERI-CYCLIZATION IN THE REACTION WITH NITRILES

As a result of hydrolysis of the nitrile group and cyclization 1-cyanomethylanthraquinones, obtained from 1-halogeno- or 1-nitroanthraquinones and cyanoacetic ester and phenylacetonitrile, are transformed into 3-substituted 2-hydroxy-7H-dibenzoquinolin-7-ones.Derivatives of the underscribed anthradipyridine were obtained from 1,5-bis(cyanomethylanthraquinones.The reaction of 1-halogeno- or 1-nitroanthraquinones with excess of malonitrile and cyanoacetic ester in the presence of potassium hydroxide in a polar aprotic solvent gave high yields of 2-amino-1,3-dicyano- and 2-amino-1,3-diethoxycarbonylbenzanthrones.The reaction of 1-cyanomethylanthraquinones with carbon disulfide in an alkaline medium led to 2-substituted 6H-anthrathiophen-6-ones as a result, probably, of closure of the thiopyran ring and recyclization.

TAUTOMERISM AND ACID-BASE CHARACTERISTICS OF 2-HYDROXY-1-AZABENZANTHRONES

In solutions of 2-hydroxy-1-azabenzanthrones in polar protic solvents tautomerism exists between the 9,10-anthraquinonoid lactim and 1,10-anthraquinonoid lactam forms.The introduction of a halogen atom at the position 3 to 6 reduces and the introduction of an amino group at the position 6 increases the content of the lactam tautomer.In acidity and basicity the lactam form of 2-hydroxy-1-azabenzanthrone surpasses the lactam form of 2-hydroxy-3-azabenzanthrone on account of an additional gain of energy through rearrangement of the 1,10-anthraquinonoid electronic structure intothe 9,10-anthraquinonoid structure during ionization.The 6-amino derivatives of 2-hydroxy- and 2-methoxy-1-azabenzanthrones are protonated first in the heterocycle and then, like 6-aminobenzanthrone, at the ketone carbonyl; they are only protonated at the amino group in the third stage; whereas 3-amino-2-methoxy-1-azabenzanthrone is protonated at the amino group immediately.