38750-39-9

Basic information

• Product Name: 7H-dibenzo[de,g]quinolin-7-one
• CAS NO: 38750-39-9
• Molecular Formula: C₁₆H₉NO
• Molecular Weight: 231.2488
• Mol File: 38750-39-9.mol

Chemical Properties

• Boiling Point: 465.4°C at 760 mmHg
• Flash Point: 238.9°C
• Density: 1.343g/cm³
• Vapor Pressure: 7.71E-09mmHg at 25°C
• Refractive Index: 1.745
• CAS DataBase Reference: 7H-dibenzo[de,g]quinolin-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7H-dibenzo[de,g]quinolin-7-one(38750-39-9)
• EPA Substance Registry System: 7H-dibenzo[de,g]quinolin-7-one(38750-39-9)

Safety Data

• Hazardous Substances Data: 38750-39-9(Hazardous Substances Data)

Upstream product

• 63927-22-0 8-bromo-isoquinoline 
• 40138-16-7 2-formylbenzene boronic acid 
• 1160852-12-9 7-oxo-7H-dibenzo[de,g]quinoline-4,5-dicarboxylic acid 
• 125442-44-6 dimethyl 7-oxo-7H-dibenzoquinoline-4,5-dicarboxylate 
• 89968-51-4 10-(methoxyimino)phenanthren-9-one 
• 101439-09-2 (2-bromophenyl)isoquinolin-1-yl-acetonitrile 
• 491-30-5 1-isoquinolone 
• 1383571-57-0 (2-bromophenyl)(isoquinolin-1-yl)methanone 
• 19658-77-6 1-iodoisoquiniline 

Relevant articles and documents

Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives

A series of new oxoaporphine derivatives were synthesized and their inhibitory activity of topoisomerase I, cytotoxicity and DNA-binding properties were studied. Oxoaporphine can strongly inhibit topoisomerase I at concentrations of 5-50'M and the cytotoxicity of the derivatives are more potent than their lead compound. Hypochromism, broadening and red shift in the absorption spectra were observed when these compounds bind to calf thymus DNA (CT DNA). These spectral characteristics were consistent with the intercalative binding of these compounds.

One-pot synthesis of oxoaporphines as potent antitumor agents and investigation of their mechanisms of actions

An efficient one-pot reaction for the synthesis of oxoaporphine alkaloids has been developed. Twenty-three compounds of oxoaporphine alkaloids were prepared and assessed for their antitumor activities. Most compounds inhibited the growth of T-24 tumor cells in vitro. Particularly, 4B displayed the most potent activity with an IC50 value of 0.5 μM, which was 19-fold more potent than the parent compound 4. The substitution at C3-position of oxoaporphine core by ?NO2 significantly enhanced the anticancer activity. Mechanism studies indicated that 4 and 4B induced cell cycle arrest at G2/M phase; in contrast, 4V induced cell cycle arrest at the S phase. Increase of mitochondrial ROS/Ca2+ and decrease of MMP, accompanied by activation of caspase-3/9, were observed in T-24 cells after exposure to compounds 4, 4B and 4V, suggesting that the mitochondrial pathway was involved in the induced apoptosis. Moreover, compound 4B effectively inhibited tumor growth in a mouse xenograft model bearing T-24.

Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine

A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.

Direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[ de,g ]quinolin-7-ones via reductive photocyclization

A series of A/D-ring substituted dibenzo[de,g]quinolin-7-ones was produced from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl ring and the phenyl group. The mechanism of the reductive photocyclization is also discussed.