832-68-8

Usage

Uses

Used in Pharmaceutical Synthesis:
Phenanthridin-6-amine is used as a building block in the synthesis of various pharmaceutical compounds, particularly for the development of anti-cancer drugs. Its unique structure and functional groups make it a valuable component in creating novel and effective therapeutic agents.
Used in Drug Discovery and Development:
Phenanthridin-6-amine is utilized in drug discovery and development due to its potential antimicrobial and antiparasitic properties. Its ability to target and interact with specific biological systems makes it a promising candidate for the creation of new drugs to combat various infections and diseases.
Used in Life Sciences Research:
In the field of life sciences, phenanthridin-6-amine is used as a fluorescent probe for the detection of biomolecules and cellular imaging. Its fluorescent properties allow researchers to visualize and study cellular processes and interactions at a molecular level, contributing to a deeper understanding of biological systems and mechanisms.
Overall, phenanthridin-6-amine is a multifaceted chemical with significant applications across various industries, including pharmaceuticals, drug discovery, and life sciences research. Its versatility and potential for further exploration make it an important tool for advancing scientific knowledge and developing innovative solutions to health-related challenges.

InChI:InChI=1/C13H10N2/c14-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)15-13/h1-8H,(H2,14,15)

Upstream product

• 229-87-8 phenanthridine 
• 2720-93-6 6-phenylphenanthridine 
• 6277-86-7 9-phenyl-9H-fluoren-9-amine 
• 7664-41-7 ammonia 
• 23564-81-0 N-phenyl-2-(2-chlorophenyl)formamidine 
• 873-32-5 2-Chlorobenzonitrile 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 15679-03-5 6-chlorophenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 
• 2157-52-0 9-fluorenone oxime 
• 486-25-9 9-fluorenone 
• 615-36-1 2-bromoaniline 
• 214360-48-2 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 
• 24310-30-3 N-biphenyl-2-yl-4-methylbenzenesulfonamide 

Downstream Products

• 109285-36-1 5-methyl-5H-phenanthridin-6-one-imine; hydriodide 
• 95953-05-2 di-phenanthridin-6-yl-amine 
• 108999-41-3 C₁₉H₁₃FN₄ 
• 108999-40-2 C₁₉H₁₃BrN₄ 
• 37694-95-4 imidazo[1,2-f]phenanthridine 
• 132141-40-3 3-Phenylimidazo<1,2-f>phenanthridine 
• 1617497-76-3 7,10-dihydrophenanthridin-6-amine 

Relevant academic research and scientific papers

Novel phenanthridine amide analogs as potential anti-leishmanial agents: In vitro and in silico insights

In the current work, sixteen novel amide derivatives of phenanthridine were designed and synthesized using 9-fluorenone, 4-Methoxy benzyl amine, and alkyl/aryl acids. The characterization of the title compounds was performed using LCMS, elemental analysis, 1HNMR, 13CNMR and single crystal XRD pattern was also developed for compounds A8. All the final analogs were screened in vitro for anti-leishmanial activity against promastigote form of L. infantum strain. Among the tested analogs, four compounds (A-06, A-11, A-12, and A-15) exhibited significant anti-leishmanial activity with EC50 value ranges from 8.9 to 21.96 μM against amastigote forms of tested L. infantum strain with SI ranges of 1.0 to 4.3. From the activity results it was found that A-11 was the most active compound in both promastigote and amastigotes forms with EC50 values 8.53 and 8.90 μM respectively. In-silico ADME prediction studies depicted that the titled compounds obeyed Lipinski's rule of five as that of the approved marketed drugs. The predicted in-silico toxicity profile also confirmed that the tested compounds were non-toxic. Finally, molecular docking and molecular dynamics study was also performed for significantly active compound (A-11) in order to study it's putative binding pattern at the active site of the selected leishmanial trypanothione reductase target as well as to understand the stability pattern of target-ligand complex for 100 ns. Single crystal XRD of compound A-08 revealed that the compound crystallizes in monoclinic C2/c space group and showed interesting packing arrangements.

Evaluation of the antiprion activity of 6-aminophenanthridines and related heterocycles

Series of 6-aminophenanthridines and related heterocyclic compounds such as benzonaphtyridines were prepared. Reduction of one of the three aromatic rings was also performed. The compounds were first tested for their antiprion activity in a previously described yeast-based colourimetric prion assay. The most potent derivatives were then assayed ex vivo against the mammalian prion PrPSc in a cell-based assay. Several of the new compounds were found more potent than the parent lead 6-aminophenanthridine. The most promising compounds against yeast and mammalian prions were 8-azido-6-aminophenanthridine (3m), and 7,10-dihydrophenanthridin-6-amine (14). In the mammalian cell-based assay, the IC50 of these two compounds were around 5 μM and 1.8 μM, respectively.

Synthesis of 6-aminophenanthridines via palladium-catalyzed insertion of isocyanides into N-sulfonyl-2-aminobiaryls

A robust route to a diverse set of 6-aminophenanthridines via palladium-catalyzed C-H activation of N-sulfonyl-2-aminobiaryl and isocyanide insertion is reported. This transformation could also provide an important approach for building core frameworks of conjugated organic polymer materials.

ORGANIC ELECTROLUMINESCENT ELEMENT AND NOVEL ALCOHOL-SOLUBLE PHOSPHORESCENT MATERIAL

Object of the present invention is to provide an organic electroluminescent element having an emissive layer that may be formed by wet process in the fabrication of the organic electroluminescence device with multi-layer structure and has excellent electron-injection property, electron-transfer property, durability and luminescent efficiency and a novel alcohol-soluble organic phosphorescent material that may be preferably applicable to the fabrication of the same. An organic electroluminescent element 1 has a plurality of laminated organic layers 4, 5, 6 sandwiched between anode 3 and cathode 7. A hole transport layer 5 composed of organic compounds insoluble in alcohol solvent and an emissive layer 6 formed by a wet process so that it contacts with the hole transport layer 5 on the side facing with the cathode 7 contains host materials consisting of one or more phosphine oxide derivatives soluble in alcohol solvent and guest materials soluble in alcohol solvent which can be excited electrically to emit light.

COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS

The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors, including TLR7 and TLR8. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine (formula I) wherein: X3 is N; X4 is N Or CR3; X5 is -CR4=CR5.

An expeditious synthesis of 6-aminophenanthridines

A simple synthesis of biologically active 6-aminophenanthridines was achieved by a Suzuki-Miyaura coupling reaction. Condensation of 2-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)aniline with 2-chlorobenzonitriles afforded 6-aminophenanthridines useful as prions inhibitors in a mild one-step procedure. The intermediate 2-amino-2′cyanobiphenyls could not be isolated.

A single step synthesis of 6-aminophenanthridines from anilines and 2-chlorobenzonitriles

Biologically active 6-aminophenanthridines were prepared in a single step procedure: Metal amides in liquid ammonia promoted the condensation of anilines with 2-chloro-benzonitriles. 6-Aminophenanthridines were isolated in moderate yield.