5-Ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide

Base Information

• Chemical Name: 5-Ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide
• CAS No.: 1239-45-8
• Molecular Formula: C21H20BrN3
• Molecular Weight: 394.314
• Hs Code.: 29339990
• Pharos Ligand ID: UA864SDLLZ5T
• Mol file: 1239-45-8.mol

Synonyms:

Chemical Property of 5-Ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide

Chemical Property:

• Appearance/Colour: Purple/maroon crystalline powder
• Melting Point: 260-262 °C (dec.)(lit.)
• Refractive Index: 1.6700 (estimate)
• Flash Point: >100°C
• PSA: 55.92000
• Density: g/cm³
• LogP: 2.29820
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL, opaque, strongly red
• Water Solubility.: 40 g/L (25 ºC)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 393.08406
• Heavy Atom Count: 25
• Complexity: 765

Purity/Quality:

98%, ^*data from raw suppliers

ETBR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T,T+
• Statements: 23-68-36/37/38-26-21/22-22
• Safety Statements: 36/37-45-36/37/39-28A-26-22-28-63

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1C2=CC(=N)C=CC2=C3C=CC(=CC3=C1C4=CC=CC=C4)N.Br
• General Description: Ethidium bromide (also known as Homidium bromide, Dromilac, and other names) is a fluorescent dye commonly used in molecular biology for DNA staining due to its strong intercalating properties with double-stranded DNA. It is often employed in competitive binding assays to evaluate the DNA-binding affinity of other ligands, as seen in studies involving chromomycin A3 analogs and distamycin analogues. Its ability to intercalate into DNA makes it a useful tool for visualizing nucleic acids in techniques like gel electrophoresis, though its mutagenic properties necessitate careful handling.

Technology Process of 5-Ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide

There total 23 articles about 5-Ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide 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: 59.0%

3,8-Bis-ethoxycarbonylamino-5-ethyl-6-phenyl-phenanthridinium; bromide (52671-22-4) → ethidium Bromide (1239-45-8)

Guidance literature:

With sulfuric acid; at 150 ℃; for 0.333333h;

Reference yield: 57.0%

3,8-dinitro-5-ethyl-6-phenylphenanthridinium ethyl sulfate (93840-65-4) → ethidium Bromide (1239-45-8)

Guidance literature:

3,8-dinitro-5-ethyl-6-phenylphenanthridinium ethyl sulfate; With sulfuric acid; iron; In ethanol; water; for 1.5h; Reflux;

With ammonia; In ethanol; water; at 25 ℃; Further stages;

DOI:10.1134/S107042721109014X

Reference yield:

2-nitro-benzidine (2243-78-9) → ethidium Bromide (1239-45-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / N,N-diethylaniline / ethanol / 0.17 h / Heating

2: 93 percent / iron, hydrochlorid acid / Heating; 1) water, 1 h, 2) aqueous ethanol, 20 min

3: 77 percent / nitrobenzene / Heating

4: 66 percent / POCl₃ / 0.75 h / Heating

5: N,N-dimethyl-acetamide / 0.5 h

6: 59 percent / diluted H₂SO₄ / 0.33 h / 150 °C

With hydrogenchloride; sulfuric acid; iron; N,N-diethylaniline; trichlorophosphate; In ethanol; N,N-dimethyl acetamide; nitrobenzene;

upstream raw materials:

3,8-dinitro-6-phenylphenanthridine

ethyl ester of p-toluenesulfonic acid

bis(ethoxycarbonylamino)-3,8 phenyl-6 phenanthridine

3,8-Bis-ethoxycarbonylamino-5-ethyl-6-phenyl-phenanthridinium; bromide

Downstream raw materials:

N-8-succinyl ethidium bromide

N-3,8-(disuccinyl) ethidium bromide

N-3,8-di(BOC-glycyl) ethidium bromide

N-8-(methyl succinyl) ethidium bromide

Refernces

New DNA binding ligands as a model of chromomycin A₃

10.1016/j.bmcl.2004.07.043

The research focuses on developing new DNA-binding ligands modeled after Chromomycin A3 (CRA3), a potent antitumor antibiotic known for binding in the minor groove of GC-rich regions of duplex DNA. The new ligands were designed to mimic CRA3's structure, particularly its trisaccharide part, using a simple alkyl group attached to the chromophore. The study successfully demonstrated that these new ligands form Mg2+-coordinated dimer complexes, exhibiting DNA-binding affinity. The synthesis involved several steps, including [4+2] cycloaddition, aldol reaction, deprotection, dehydroxylation, and hydrogenation. The ligands' Mg2+-binding properties were investigated using UV spectra, and their DNA-binding affinity was evaluated through a competitive displacement assay with ethidium bromide (ETBr) and self-complementary DNA duplexes. The experiments showed that the alkyl chain in the new ligands contributes significantly to the formation of dimer complexes and DNA binding, with the 3(S) isomer showing high affinity to DNA in the presence of MgCl2. The study concluded that the simple alkyl chain can mimic some roles of the trisaccharide part for Mg2+-dimer complex formation and Mg2+-mediated DNA binding, and further efforts are underway to develop stronger DNA-binding ligands based on this model.

Synthesis and biological evaluation of distamycin analogues - New potential anticancer agents

10.1002/ardp.200800122

The study focuses on the synthesis and biological evaluation of eight distamycin analogues, which are potential anticancer agents designed to bind to the minor groove of B-DNA. These analogues were tested for their in-vitro cytotoxicity against human breast cancer cell lines MCF-7 and MDA-MB-231. The chemicals used in the study include distamycin analogues (compounds 1–8), ethidium bromide for DNA binding assays, and topoisomerase I and II enzymes for assessing the compounds' inhibitory activity. The purpose of these chemicals was to evaluate the analogues' antiproliferative and cytotoxic effects, their interaction with DNA, and their potential to inhibit DNA topoisomerases, which are key enzymes in cellular processes and targets for anticancer drug development. The study aimed to identify potential new anticancer agents with strong cytotoxic effects and DNA binding capabilities.