144511-12-6

Basic information

• Product Name: PSQ03
• Synonyms: PSQ03
• CAS NO: 144511-12-6
• Molecular Formula: C₁₃H₇F₂NO₃
• Molecular Weight: 263.1963864
• EINECS: -0
• Mol File: 144511-12-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PSQ03(CAS DataBase Reference)
• NIST Chemistry Reference: PSQ03(144511-12-6)
• EPA Substance Registry System: PSQ03(144511-12-6)

Safety Data

• Hazardous Substances Data: 144511-12-6(Hazardous Substances Data)

Upstream product

• 4664-08-8 cinchomeronic anhydride 
• 490-11-9 3,4-pyridinecarboxylic acid 
• 540-36-3 para-difluorobenzene 

Downstream Products

• 144511-13-7 6,9-difluorobenzoisoquinoline-5,10-dione 

Relevant articles and documents

New anthracenedione derivatives with improved biological activity by virtue of stable drug-DNA adduct formation

Mitoxantrone is an anticancer agent that acts as a topoisomerase II poison, however, it can also be activated by formaldehyde to form DNA adducts. Pixantrone, a 2-aza-anthracenedione with terminal primary amino groups in its side chains, forms formaldehyde-mediated adducts with DNA more efficiently than mitoxantrone. Molecular modeling studies indicated that extension of the "linker" region of anthracenedione side arms would allow the terminal primary amino greater flexibility and thus access to the guanine residues on the opposite DNA strand. New derivatives based on the pixantrone and mitoxantrone backbones were synthesized, and these incorporated primary amino groups as well as extended side chains. The stability of DNA adducts increased with increasing side chain length of the derivatives. A mitoxantrone derivative bearing extended side chains (7) formed the most stable adducts with ～100-fold enhanced stability compared to mitoxantrone. This finding is of great interest because long-lived drug-DNA adducts are expected to perturb DNA-dependent functions at all stages of the cell cycle.

Hetero-annulated indazoles

This invention is directed to heteroannulated indazoles namely to 2,5-disubstituted quinolino-, isoquinolino-, phthalazino-, and quinoxalino- annulated indazole-6(2H)-ones and related mono N-oxides. These compounds have been shown to have antitumor activity.

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

In the search for novel heteroanalogs of anthracendiones, 6,9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione dimaleate salt (BBR 2778), was selected as the most promising compound. New methods of synthesis produce the compound in purity greater than 99%.

2-aminoalkyl-5-aminoalkylamino substituted-isoquinoindazole-6(2H)-ones

This invention is directed to 2-aminoalkyl-5-aminoalkylamino substituted isoquino [8,7,6-cd]indazole-6-(2H)-ones and to 2-aminoalkyl-5-aminoalkylamino substituted-isoquino [5,6,7-cd] indazole-6(2H)-ones. These compounds have been shown to have antitumor activity.

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.