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5H-(1,3)Dioxolo(5,6)indeno(1,2-C)isoquinoline-5,12(6H)-dione, 6-(3-((2-hydroxyethyl)amino)propyl)-2,3-dimethoxy-

HCID 397888
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Basic information

CAS
308246-52-8
Standard SMILES
COc1cc2c3c(n(CCCNCCO)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2
InChIKey
QCSDJDQOJBQTDV-UHFFFAOYSA-N
Molecular formula
C24H24N2O7
Average molar mass
452.5 g/mol
Monoisotopic mass
452.15835111

Overview

Topoisomerase-1 Inhibitor LMP744 is an indenoisoquinoline derivative and topoisomerase 1 (Top1) inhibitor, with potential antineoplastic activity. Upon administration, LMP744 binds to and stabilizes cleaved DNA-Top1 complexes, which prevents DNA re-ligation, induces stable, irreversible DNA strand breaks, prevents DNA repair, and leads to cell cycle arrest and apoptosis. As tumor cells proliferate at a much higher rate than normal cells, LMP744 specifically targets cancer cells. Top1, a DNA modifying enzyme essential for transcription, replication, and repair of double-strand DNA breaks, is overexpressed in tumor cells.

Names & identifiers

Preferred name
5H-(1,3)Dioxolo(5,6)indeno(1,2-C)isoquinoline-5,12(6H)-dione, 6-(3-((2-hydroxyethyl)amino)propyl)-2,3-dimethoxy-
IUPAC
20-[3-(2-hydroxyethylamino)propyl]-15,16-dimethoxy-5,7-dioxa-20-azapentacyclo[10.8.0.02,10.04,8.013,18]icosa-1(12),2,4(8),9,13,15,17-heptaene-11,19-dione
English name
LMP744
Molecular formula
C24H24N2O7
Molecular weight
452.45656

Names & synonyms

LMP744308246-52-8LMP-744MJ-III-65NSC-706744NCI60_037977NSC-70674329BY7HQV0TCHEMBL126159Topoisomerase-1 inhibitor lmp7445H-(1,3)Dioxolo(5,6)indeno(1,2-C)isoquinoline-5,12(6H)-dione, 6-(3-((2-hydroxyethyl)amino)propyl)-2,3-dimethoxy-6-(3-((2-hydroxyethyl)amino)propyl)-2,3-dimethoxy-5H-[1,3]dioxolo[4',5':5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione
Show more names
LMP744,LMP-744LMP744 (MJ-III655H-[1,3]Dioxolo[5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione, 6-[3-[(2-hydroxyethyl)amino]propyl]-2,3-dimethoxy-6-(3-((2-hydroxyethyl)amino)propyl)-2,3-dimethoxy-5H-[1,3]dioxolo[4,5:5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione(WXG02929)20-{3-[(2-hydroxyethyl)amino]propyl}-15,16-dimethoxy-5,7-dioxa-20-azapentacyclo[10.8.0.02,1?.0?,?.013,1?]icosa-1(12),2(10),3,8,13(18),14,16-heptaene-11,19-dione
6-[3-[(2-Hydroxyethyl)amino]propyl]-2,3-dimethoxy-5H-[1,3]dioxolo[5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione20-[3-(2-Hydroxyethylamino)propyl]-15,16-dimethoxy-5,7-dioxa-20-azapentacyclo[10.8.0.02,10.04,8.013,18]icosa-1(12),2,4(8),9,13,15,17-heptaene-11,19-dioneLMP744 free base6-(3-(2-hydroxyethyl)amino-1-propyl)-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno(1,2-)isoquinoline308246-52-8 (free base)UNII-29BY7HQV0Torb1709250SCHEMBL4162998

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
107 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
8
Heavy atoms
33
Formal charge
0
Complexity
802

Physicochemical properties

Melting point
231 · 231-234 °C
Boiling point
748.1 · 748.1±60.0 °C(Predicted)
Density
1.46 · 1.46±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO
form
Solid
pka
14.79 · 14.79±0.10(Predicted)
color
Brown to dark brown
FDA UNII
29 BY7HQV0T · 29BY7HQV0T

Chemistry & industry

Applications

UsesLMP744 (MJ-III65) is a DNA intercalator and Topoisomerase I (Top1) inhibitor with antitumor activity[1].

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Database identifiers

CAS
308246-52-8
PubChem CID
397888
DTXSID
DTXSID30327954
ChEMBL
CHEMBL126159
UNII
29BY7HQV0T
Nikkaji
J1.431.138F