Benz[a]acridine

Base Information

• Chemical Name: Benz[a]acridine
• CAS No.: 225-11-6
• Molecular Formula: C17H11 N
• Molecular Weight: 229.281
• Hs Code.: 2933990090
• European Community (EC) Number: 205-929-7
• UNII: D4Q8MR98LU
• DSSTox Substance ID: DTXSID9075371
• Nikkaji Number: J38.204C
• Wikidata: Q27155920
• Mol file: 225-11-6.mol

Synonyms:benz(a)acridine

Chemical Property of Benz[a]acridine

Chemical Property:

• Vapor Pressure: 9.76E-08mmHg at 25°C
• Melting Point: 131 °C
• Refractive Index: 1.783
• Boiling Point: 446.2 °C at 760 mmHg
• PKA: 4.71±0.25(Predicted)
• Flash Point: 201.4 °C
• PSA: 12.89000
• Density: 1.239 g/cm³
• LogP: 4.54120
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 229.089149355
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

Benz[a]acridine BCR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=NC4=CC=CC=C4C=C32
• General Description: BENZO(A)ACRIDINE, also known as 1,2-Benzacridine or 7-Azabenz[a]anthracene, is a polycyclic aromatic compound structurally related to benzacridine derivatives. The referenced study indicates that certain benzacridine derivatives, such as compound **14**, exhibited no significant antitumor, DNA intercalative, or topoisomerase II-dependent DNA cleavage activity, in contrast to more active analogs like **21**. The findings suggest that the biological activity of benzacridine derivatives is highly dependent on structural modifications, particularly chromophore planarity and specific functional groups, which influence their DNA-binding and antitumor properties.

Technology Process of Benz[a]acridine

There total 49 articles about Benz[a]acridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

benzo[a]acridin-12-yl(phenyl)methanone → benz[a]acridine (225-11-6)

Guidance literature:

With sodium hydroxide; In tert-butyl alcohol; at 110 ℃; for 24h; regioselective reaction; Sealed tube;

DOI:10.1039/c9cc03375k

Reference yield: 69.0%

1-[(2-aminophenyl)morpholin-4-yl-methyl]naphthalen-2-ol → benz[a]acridine (225-11-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; for 5h; under 760.051 Torr;

DOI:10.1002/open.201900150

Reference yield: 65.0%

7,12-dihydro-benzo[a]acridine (32638-83-8) → benz[a]acridine (225-11-6)

Guidance literature:

With potassium dichromate; sulfuric acid; In water; for 0.25h; Heating;

DOI:10.1039/P19800001233

upstream raw materials:

8,9,10,11-tetrahydro-benzo[a]acridine

7,12-dihydro-benzo[a]acridine

2-Nitrobenzyl alcohol

N-Phenyl-2-naphthylamine

Refernces

Synthesis and antitumor activity of fused quinoline derivatives

10.1248/cpb.38.3048

The study investigates the synthesis and biological properties of various fused quinoline derivatives, specifically focusing on their DNA intercalative properties, cytotoxicity against KB cells, antitumor activity in P388 leukemia mice, and ability to induce topoisomerase II-dependent DNA cleavage. Key chemicals involved include the indoloquinoline derivative 9 and the dihydrobenz[a]acridine derivative 14. Compound 9, synthesized by replacing the methylene group in 4a with an imino group, exhibited potent antitumor activity, intercalated DNA, and induced topoisomerase II-dependent DNA cleavage at low doses. In contrast, 14 was inactive in all assays. The study also examined other benzacridine derivatives (15, 20, and 21), finding that 21 showed potent activities in all assays, while 15 and 20 were less active. The research highlights the importance of chromophore planarity and structural features in determining the intercalative ability and antitumor activity of these compounds, with 9 being the most potent in this series.