Acridine

Base Information

• Chemical Name: Acridine
• CAS No.: 260-94-6
• Molecular Formula: C13H9N
• Molecular Weight: 179.221
• Hs Code.: 29333990
• European Community (EC) Number: 205-971-6
• NSC Number: 3408
• UN Number: 2713
• UNII: 42NI1P5Q1X
• DSSTox Substance ID: DTXSID8059766
• Nikkaji Number: J2.978E
• Wikipedia: Acridine
• Wikidata: Q342713
• NCI Thesaurus Code: C203
• Metabolomics Workbench ID: 133466
• ChEMBL ID: CHEMBL39677
• Mol file: 260-94-6.mol

Synonyms:Acridine;Acridines

Chemical Property of Acridine

Chemical Property:

• Appearance/Colour: colourless to light yellow crystals
• Vapor Pressure: 0.000113mmHg at 25°C
• Melting Point: 106-109 °C
• Refractive Index: 1.726
• Boiling Point: 346.726 °C at 760 mmHg
• PKA: 5.58(at 20℃)
• Flash Point: 153.796 °C
• PSA: 12.89000
• Density: 1.188 g/cm³
• LogP: 3.38800
• Storage Temp.: Refrigerator
• Solubility.: dioxane: 0.1 g/mL, clear
• Water Solubility.: 57.35mg/L(24 oC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 179.073499291
• Heavy Atom Count: 14
• Complexity: 181
• Transport DOT Label: Poison

Purity/Quality:

98% min ^*data from raw suppliers

Acridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-68-36/37/38
• Safety Statements: 22-36-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Acridine Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=N2
• Uses: A quinoline derivative used as manufacturing dyes and as intermediate for antileishmanial agents. A catabolic product of carbamazepine (C175840) metabolite. manufacture of dyes and intermediates; some dyes derived from it are used as antiseptics, e.g. 9-aminoacridine, acriflavine and proflavine. The hydrochloride has been used as reagent for cobalt, iron and zinc. Acridine is a compound occurring in coal tar that has been used in the manufacture of dyes and intermediates. Derivatives are used as antiseptics (e.g., proflavine). Acridine is a strong irritant to mucous membranes and skin, and it causes sneezing on inhalation.

Technology Process of Acridine

There total 234 articles about 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: 73.0%

acridine-9-carboxylic acid (5336-90-3) → acridine (260-94-6) + 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 130 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201204169

Reference yield: 63.0%

o-aminobenzaldehyde (529-23-7) + phenylboronic acid (98-80-6) → acridine (260-94-6) + 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With pyridine; oxygen; copper(II) nitrate; In dimethyl sulfoxide; at 130 ℃; for 24h; under 760.051 Torr;

DOI:10.1021/acs.orglett.8b00957

Reference yield: 51.0%

acridine (92-81-9) → acridine (260-94-6) + 10H-acridin-9-one (578-95-0,790240-54-9)

Guidance literature:

With oxygen; 1-(2,2-diphenyl-2λ⁴,3λ⁴-[1,3,2]diazaborolo[4,5,1-ij]quinolin-1(2H)-yl)-3-phenylpropan-1-one; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 5h; Irradiation; Green chemistry;

DOI:10.1039/d1gc01063h

upstream raw materials:

1,2,3,4-tetrahydroacridine

acridine

ethanol

2,2'-azobis(isobutyronitrile)

Downstream raw materials:

9-(phenylmethyl)acridine

9,10-dibenzyl-9,10-dihydro-acridine

9-triphenylsilyl-10-methylacridane

10-methyl-9, 10-dihydro-9-acridinone

Refernces

Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position

10.1016/j.ejmech.2011.04.016

The research focuses on the synthesis and evaluation of functionalized quinacrine analogs for their anti-prion activities and drug-like potential. The study involves the replacement of the basic alkyl side chain of quinacrine with various 4-(substituted phenyl)piperazinyl and 1-benzylpiperidin-4-yl moieties to derive new analogs. The anti-prion activity of these analogs was assessed using different prion-infected murine cell models, with potency, activity across models, and binding affinities to a human prion protein fragment (hPrP121e231) being key parameters. The experiments included cell-based assays to determine the effective concentration reducing PrPSc content (EC50), full anti-prion activity (FAA), and maximal tolerant concentration (TC). Additionally, the binding affinities were measured using surface plasmon resonance (SPR), and permeability across the blood-brain barrier was evaluated using the PAMPA-BBB assay. The analogs were also tested for their susceptibility to P-glycoprotein (Pgp) efflux activity, which can limit brain accumulation. The reactants used in the synthesis of these analogs included amines, acridine derivatives, and other chemical moieties, while analyses involved NMR, MS, HPLC, and combustion analysis to confirm the structures and purities of the synthesized compounds.