4589-37-1

Usage

Chemical compound

5-hydroxybenzo[g]isoquinoline-6,9,10(2H)-trione
Belongs to isoquinoline-6,9,10(2H)-trione family
Derivative of isoquinoline

Molecular structure

benzo ring fused to an isoquinoline ring, hydroxy group at the 5th position, carbonyl groups at the 6th, 9th, and 10th positions
Studied for potential pharmaceutical properties
Potential applications in medicinal chemistry and drug development
Biological activities include anti-inflammatory, analgesic, and antitumor effects
Further research needed to explore full range of potential uses and properties.

Upstream product

• 4664-08-8 cinchomeronic anhydride 
• 123-31-9 hydroquinone 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 144510-94-1 6,9-bis<<2-ethyl>amino>benzoisoquinoline-5,10-dione 
• 144510-96-3 6,9-bis{[2-(amino)ethyl]amino}benzo[g]isoquinoline-5,10-dione 

Relevant academic research and scientific papers

6, 9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5, 10-dione dimaleate and synthesis technology thereof

The invention discloses a synthesis technology of 6, 9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5, 10-dione dimaleate and relates to the technical field of antineoplastic drug synthesis. The synthesis technology comprises that 3, 4-pyridinedicarboxylic anhydride and hydroquinone undergo a reaction in the presence of a catalyst to produce a first intermediate, the first intermediate and N-t-butoxycarbonylethylenediamine undergo a reaction to produce a second intermediate, the second intermediate is subjected to deprotection, and the product and maleic acid undergo a salt forming reaction to produce a product. The prepared product has purity greater than 99.5% and known single impurity and unknown single impurity contents less than 0.1%. The important intermediate of the synthesis technology has stable properties and is convenient for storage. The synthesis technology allows mild reaction conditions, has simple processes, realizes a low cost and is suitable for industrial production. The invention also provides pixantrone dimaleate. The pixantrone dimaleate can be processed to form a freeze-dried powder injection for treating human aggressive non-Hodgkin's lymphoma with easy recurrence and high treatment difficulty.

6,9-Bisbenzoisoquinoline-5,10-diones. A Novel Class of Chromophore-Modified Antitumor Anthracene-9,10-diones: Synthesis and Antitumor Evaluations

Synthetic procedures have been developed which lead to the 2-aza congeners 3 and several related N-oxides 4.The analoques 3 exhibited a wide range of in vitro cytotoxicity against L1210 leukemia, the human colon adenocarcinoma cell line LoVo, and the doxorubicin resistant LoVo/DX cell line.Selected analogues of 3 showed significant P388 antileukemic activity in mice with 3c exhibiting high activity.This activity was also retained in the related N-oxide 4a.These heterocyclic bioisosteric models are representative of the first anthracene-9,10-diones which display antileukemic activity comparable to mitoxantrone.

Synthesis of Azaanthraquinones: Homolytic Substitution of Pyridines

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6.In particular, derivatives of pyridine-3-carbonitrile have been benzoylated at positions 2 and 4.Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1- and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).