113250-80-9

Upstream product

• 113250-73-0 [1-(2-Chloro-phenyl)-meth-(E)-ylidene]-naphthalen-1-yl-amine 
• 134-32-7 1-amino-naphthalene 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 89-98-5 2-chloro-benzaldehyde 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 113250-73-0 (2-chloro-benzylidene)-[1]naphthyl-amine 

Downstream Products

• 218-38-2 benzo[c]phenanthridine 
• 6361-33-7 N-(1-naphthyl)benzylamine 
• 634-41-3 N-(2-methylphenyl)-1-naphthylamine 
• 1158798-85-6 C₂₀H₁₈ClN 
• 1310480-62-6 1-(2-chlorobenzyl)-3,3-dimethyl-1-(naphthalen-1-yl)urea 

Relevant academic research and scientific papers

Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions

The photostimulated reaction of N-(2-halo-benzyl)aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the SRN1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo[a]phenanthridine (98%), and benzo[c]phenanthridine (84%) were synthesized.

Use of Quantitative Structure - Activity Relationship (QSAR) and ADMET prediction studies as screening methods for design of benzyl urea derivatives for anti-cancer activity

2D and 3D quantitative structure-activity relationship studies have been carried out for establishing a correlation between the structural properties of benzyl urea derivatives and their anti-tumour activities. From this correlation, the new chemical entities were designed, and their activity and absorption, distribution, metabolism, excretion, and toxicity properties were also predicted. Finally, the most promising compounds from these screening were synthesized and biologically evaluated for their anti-cancer properties. Compound 1-(2, 4-dimethylphenyl)-3, 3-dimethyl-1-(2-nitrobenzyl) urea (7d) showed significant anti-proliferative activity (at 100 μg/mL) in human cancer cell lines-T-cell leukemia (Jurkat J6), myelogenous leukemia (K562), and breast cancer (MCF-7) compared to reference standard 5-flurouracil.

Electron-transfer-mediated synthesis of phenanthridines by intramolecular arylation of anions from n-(ortho-Halobenzyl)arylamines: regiochemical and mechanistic analysis

The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(orrAo-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of orthohalobenzylchlorides with different arylamines. The reaction of the anions of a diverse set N-(orthohalobenzyl)arylamines was studied, and the methodology was extended to the synthesis of trispheridine, a natural product, in very good yield, In order to explain the regiochemical outcome of these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.

Benzyne Cyclization Route to Benzophenanthridine Alkaloids. Synthesis of Chelerythrine, Decarine, and Nitidine

The alkaloids chelerythrine (8b) and decarine (7c) have been synthesized through a benzyne-mediated cyclization of N-(2-halobenzyl)-1-naphthylamines 4 with KNH2 in ammonia/ether.The 7-hydroxybenzophenanthridine structure 16a proposed for the alkaloid fagaridine is questioned on the basis of comparison with a model compound (16b) synthesized by benzyne cyclization.For the 8,9-oxygenated alkaloids like nitidine (8i), this cyclization proceeded poorly, but a dramatic improvement occurred when LDA/THF at -78 deg C was used instead of KNH2/NH3.