144510-89-4

Basic information

• Product Name: 6,9-bis{[2-(diethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione
• Synonyms: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-(diethylamino)ethyl)amino)-; benz[g]isoquinoline-5,10-dione, 6,9-bis[[2-(diethylamino)ethyl]amino]-
• CAS NO: 144510-89-4
• Molecular Formula: C₂₅H₃₅N₅O₂
• Molecular Weight: 437.5777
• Mol File: 144510-89-4.mol

Chemical Properties

• Boiling Point: 633.4°C at 760 mmHg
• Flash Point: 336.9°C
• Density: 1.18g/cm³
• Vapor Pressure: 5.99E-16mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 6,9-bis{[2-(diethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6,9-bis{[2-(diethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione(144510-89-4)
• EPA Substance Registry System: 6,9-bis{[2-(diethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione(144510-89-4)

Safety Data

• Hazardous Substances Data: 144510-89-4(Hazardous Substances Data)

Upstream product

• 100-36-7 N,N-diethylethylenediamine 
• 144511-13-7 6,9-difluorobenzoisoquinoline-5,10-dione 
• 4664-08-8 cinchomeronic anhydride 
• 490-11-9 3,4-pyridinecarboxylic acid 

Relevant articles and documents

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.

6,9 Bis(substituted-amino)benzo-[g]isoquinoline-5,10-diones

A compound according to formula (I): wherein R is, C1-C10 alkyl; phenyl or C7-C10 aralkyl;, C2-C10 aklyl substituted with one or two substituents selected from the group consisting of OR1 and -NR2R3;, C2-C10 alkyl interrupted by one or two oxygen atoms or by a member selected from the group consisting of -NR4-, cis-CH=CH, trans-CH=CH- and -C=C-, and optionally substituted with one or two hydroxy (OH) or -NR2R3 groups; and wherein, R1 is selected from the group consisting of hydrogen, C1-C6 alkyl, phenyl, C7-C10 aralkyl, -CHO, -COR5-, -COOR5, -S(O2)R5 and C2-C6 alkyl optionally substituted with -NR2R3;, R2 and R3 are the same or different and are selected from the group consisting of hydrogen, C1-C10 alkyl, C7-C10 aralkyl, phenyl, C2-C10 alkyl substituted with one or two hydroxy (OH) groups, -CHO, -COR5, -COOR5, and -S(O2)R5, R2 and R3 taken together with the nitrogen atom to which they are bound form an ethyleneimine ring or a 5- or 6-membered aromatic or non-aromatic heterocyclic ring optionally containing another heteroatom selected from the group consisting of sulfur, oxygen and nitrogen, R2 is H and R3 is -C(=NH)NH2 or R2 is -C(=NH)NH2 and R3 is H;, R4 is selected from the group consisting of hydrogen, C1-C10 alkyl, C2-C10 hydroxyalkyl, C2-C10 alkyl substituted with -NR2R3, C7-C10 aralkyl, phenyl, -COR5, -COOR5 and -S(O2)R5;, R5 is selected from the group consisting of C1-C10 alkyl, C7-C10 aralkyl, α-, β-, or γ-naphthyl, phenyl, o-, m-, or p-tolyl as free bases and their salts with pharmaceutically acceptable acids, have been found to have cytostatic and anti-tumor activity.