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138154-39-9

138154-39-9 | 6H-Imidazo[4,5,1-de]acridin-6-one, 5-[[2-(diethylamino)ethyl]amino]-8-hydroxy-

CAS No: 138154-39-9 Catalog No: AG00183K MDL No:

Product Description

Catalog Number:
AG00183K
Chemical Name:
6H-Imidazo[4,5,1-de]acridin-6-one, 5-[[2-(diethylamino)ethyl]amino]-8-hydroxy-
CAS Number:
138154-39-9
Molecular Formula:
C20H22N4O2
Molecular Weight:
350.4143
IUPAC Name:
10-[2-(diethylamino)ethylamino]-5-hydroxy-1,14-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-2(7),3,5,9,11,13(16),14-heptaen-8-one
InChI:
InChI=1S/C20H22N4O2/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3
InChI Key:
CUNDRHORZHFPLY-UHFFFAOYSA-N
SMILES:
CCN(CCNc1ccc2c3c1c(=O)c1cc(O)ccc1n3cn2)CC
UNII:
MZ4Y5H4OAB

Properties

Complexity:
512  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
350.174g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
350.422g/mol
Monoisotopic Mass:
350.174g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
70.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.6  

Literature

Title Journal
Role of human UDP-glucuronosyltransferases in the biotransformation of the triazoloacridinone and imidazoacridinone antitumor agents C-1305 and C-1311: highly selective substrates for UGT1A10. Drug metabolism and disposition: the biological fate of chemicals 20120901
Influence of temperature and interactions with ligands on dissociation of dsDNA and ligand-dsDNA complexes of various types of binding. An electrochemical study. Physical chemistry chemical physics : PCCP 20120314
Novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2): crystal structures, biochemical activity, and intracellular effects of imidazoacridin-6-ones. Journal of medicinal chemistry 20111013
Anticancer imidazoacridinone C-1311 inhibits hypoxia-inducible factor-1α (HIF-1α), vascular endothelial growth factor (VEGF) and angiogenesis. Cancer biology & therapy 20111001
The imidazoacridinone antitumor drug, C-1311, is metabolized by flavin monooxygenases but not by cytochrome P450s. Drug metabolism and disposition: the biological fate of chemicals 20110801
Cytotoxicity studies of some novel fluoro acridone derivatives against sensitive and resistant cancer cell lines and their mechanistic studies. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20110717
Use of yeast chemigenomics and COXEN informatics in preclinical evaluation of anticancer agents. Neoplasia (New York, N.Y.) 20110101
Imidazoacridin-6-ones as novel inhibitors of the quinone oxidoreductase NQO2. Bioorganic & medicinal chemistry letters 20100501
Structural determinants of imidazoacridinones facilitating antitumor activity are crucial for substrate recognition by ABCG2. Molecular pharmacology 20090501
Thermoresponsive polymeric gel as a medium for examining interactions between dsDNA and an anticancer drug. Analytical and bioanalytical chemistry 20081001
Sequential induction of mitotic catastrophe followed by apoptosis in human leukemia MOLT4 cells by imidazoacridinone C-1311. Apoptosis : an international journal on programmed cell death 20071201
Electroanalytical and spectroscopic procedures for examination of interactions between double stranded DNA and intercalating drugs. Analytical and bioanalytical chemistry 20071101
Comparative evaluation of C1311 cytotoxic activity and interference with cell cycle progression in a panel of human solid tumour and leukaemia cell lines. International journal of oncology 20071001
Comparative cytotoxicity of C-1311 in colon cancer in vitro and in vivo using the hollow fiber assay. Journal of chemotherapy (Florence, Italy) 20071001
C421 allele-specific ABCG2 gene amplification confers resistance to the antitumor triazoloacridone C-1305 in human lung cancer cells. Biochemical pharmacology 20070630
The hollow fibre model--facilitating anti-cancer pre-clinical pharmacodynamics and improving animal welfare. International journal of oncology 20061201
Development and validation of an LC-UV method for the quantification and purity determination of the novel anticancer agent C1311 and its pharmaceutical dosage form. Journal of pharmaceutical and biomedical analysis 20050901
Compatibility and stability of the novel anti-cancer agent C1311 in infusion devices and its in vitro biocompatibility. Journal of oncology pharmacy practice : official publication of the International Society of Oncology Pharmacy Practitioners 20050301
Pharmaceutical development of a parenteral lyophilised dosage form for the novel anticancer agent C1311. PDA journal of pharmaceutical science and technology 20050101
Similarity between enzymatic and electrochemical oxidation of 2-hydroxyacridinone, the reference compound of antitumor imidazoacridinones. Acta biochimica Polonica 20030101

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