218-38-2

Usage

Uses

Given the highly toxic and carcinogenic nature of 5-Azachrysene, its direct use in applications is limited due to the associated health risks. However, research and regulatory efforts are focused on understanding its toxicological effects and developing measures to mitigate its impact on human health and the environment.
Used in Environmental and Occupational Health Research:
5-Azachrysene is utilized as a subject of study in research aimed at understanding the mechanisms of its carcinogenic effects and DNA damage induction. This research is crucial for developing strategies to reduce exposure and manage the risks associated with this chemical.
Used in Regulatory Measures Development:
5-Azachrysene serves as a key chemical in the development of regulatory measures and guidelines to control its emission and presence in the environment. Efforts in this area aim to minimize the impact of 5-Azachrysene on public health and environmental safety.
While 5-Azachrysene itself is not used in a positive application due to its harmful effects, the knowledge gained from studying its properties and impacts is invaluable for creating safer environments and informing public health policies.

InChI:InChI=1/C17H11N/c1-4-8-15-12(5-1)9-10-16-14-7-3-2-6-13(14)11-18-17(15)16/h1-11H

Upstream product

• 59115-71-8 5H-benzo[c]phenanthridin-6-one 
• 66644-26-6 N-(2-phenyl-[1]naphthyl)-formamide 
• 19730-92-8 7,8,9,10-tetrahydro-benzo[c]phenanthridine 
• 154283-46-2 6-chloro-benzo[c]phenanthridine 
• 855290-02-7 benzo[c]phenanthridine-6-carboxylic acid 
• 109601-95-8 11-azido-11H-benzo[a]fluorene 
• 4070-41-1 8-hydroxydihydosanguinarine 
• 76862-54-9 Benzotetrazolo<1,5-f>phenanthridine 
• 113250-73-0 [1-(2-Chloro-phenyl)-meth-(E)-ylidene]-naphthalen-1-yl-amine 
• 113250-95-6 benzo[c]phenanthridine 
• 98799-47-4 11,12-Dihydro-benzo[c]phenanthridine 
• 113250-80-9 (2-chlorobenzyl)(naphthalen-1-yl)amine 
• 55377-53-2 11,12-dihydrobenzo[c]phenanthridin-6-(5H)-one 
• 529-19-1 2-Methylbenzonitrile 

Relevant academic research and scientific papers

A new synthetic approach to the benzo[c]phenanthridine ring system

The base-catalyzed reaction of 2-methylbenzonitrile and paraformaldehyde provided 6-amino-11,12-dihydrobenzo[c]phenanthridine, which was converted via the corresponding 6-oxo- and 6-thioxo-derivatives into benzo[c]phenanthridine.

A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction

The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.

Sanguinarine as a new chemical entity of thioredoxin reductase inhibitor to elicit oxidative stress and promote tumor cell apoptosis

The alteration of redox homeostasis is a hallmark of cancer cells. As a critical player in regulating cellular redox signaling, thioredoxin reductase (TrxR) enzymes are increasingly recognized as attractive targets for anticancer drug development. We repo

Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines

A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima-Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related natural products can be derived. The synthetic utility of this method by the quick assembly of the natural product trispheridine is also demonstrated.

Synthesis method of phenanthridine and derivative of phenanthridine

The invention discloses a synthesis method of phenanthridine as shown in a formula (I) and a derivative of the phenanthridine. In the synthesis method, o-arylphenylsulfimide shown as a formula (II) isused as a raw material and reacts in an organic solvent under the action of a [Cu]/Selectfluor catalyst to obtain a corresponding target product (I). The synthesis method disclosed by the invention has the advantages of cheap and easily available and low-toxicity catalyst, environmental friendliness, mild reaction conditions, high universality of functional group and easiness and convenience in operation. The formulas (I) and (II) are shown in the description.

Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C?H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-N-Ms-arylamines with Benzyl Halides/Sulfonates

An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram-scale preparation.

A preparation method of compound phenanthridine apperception (by machine translation)

The invention discloses a method for preparing phenanthridine apperception composition, comprising: adding the reactant in the solvent 2 - halogenated -N- Protection of the aromatic amine and benzylic or benzyl sulfonic acid ester compound, then adding metal palladium catalyst, a ligand and an alkali, in heating and inert gas protection under the conditions of the chemical reaction, the reaction is complete after treatment to obtain the compound of the present invention pure product. Preparation method of this invention adopts the simple and easily obtained 2 - halogenated -N- Protection of the aromatic amine and benzylic or benzyl sulfonic acid ester compound as a raw material, by nucleophilic substitution/C - H activation/aromatization series reaction to obtain the phenanthridine compound, with raw materials are easy, simple operation, after treatment is simple, and high yield. (by machine translation)

Palladium-Catalyzed Nucleophilic Substitution/C-H Activation/Aromatization Cascade Reaction: One Approach to Construct 6-Unsubstituted Phenanthridines

A facile and practical palladium-catalyzed nucleophilic substitution/C-H activation/aromatization cascade reaction has been developed. A range of 6-unsubstituted phenanthridines could be obtained in moderate to good yields (31-85%) with readily prepared N-Ms arylamines and commercially available 2-bromobenzyl bromide derivatives as starting materials. The potential application of the protocol was also demonstrated by the expeditious synthesis of the natural alkaloid trisphaeridine.

Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines

A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.