15679-03-5

Usage

Uses

Used in Pharmaceutical Synthesis:
6-chlorophenanthridine is utilized as a building block in the synthesis of various pharmaceuticals and organic compounds, contributing to the development of new drugs with diverse therapeutic applications.
Used in Antimicrobial Applications:
6-chlorophenanthridine is employed as an antimicrobial agent, leveraging its potential to combat infections caused by various microorganisms, thereby serving as a crucial component in the development of new antimicrobial drugs.
Used in Anticancer Applications:
In the field of oncology, 6-chlorophenanthridine is used as an anticancer agent, targeting the inhibition of tumor growth and progression, and potentially offering new therapeutic options for cancer treatment.
Used in Anti-inflammatory Applications:
6-chlorophenanthridine is used as an anti-inflammatory agent, potentially mitigating inflammation and associated symptoms, contributing to the development of novel treatments for inflammatory conditions.
Used in Antifungal Applications:
6-chlorophenanthridine is also studied for its potential use as an antifungal agent, indicating its possible role in treating fungal infections and further expanding its therapeutic applications.
Used in Disease Treatment Research:
6-chlorophenanthridine is explored for its potential in the treatment of various diseases, reflecting its broad-spectrum biological activity and the ongoing quest to harness its properties for medical advancements.

InChI:InChI=1/C13H8ClN/c14-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)15-13/h1-8H

Upstream product

• 1015-89-0 6(5H)-phenanthridinone 
• 14548-01-7 phenanthridine N-oxide 
• 17337-13-2 [1,1'-biphenyl]-2-yl-isocyanate 
• 138344-50-0 tert-butyl [1,1′-biphenyl]-2-ylcarbamate 
• 115293-14-6 1,3-di(biphenyl-2-yl)urea 
• 90-41-5 2-phenylaniline 
• 1015-89-0 phenanthridin-6-ol 
• 79-37-8 oxalyl dichloride 
• 2157-52-0 9-fluorenone oxime 
• 486-25-9 9-fluorenone 
• 6747-35-9 2-carboxy-2'-(aminocarboxyl)-1,1'-biphenyl 
• 229-87-8 phenanthridine 
• 173379-08-3 1,1'-biphenyl-2-yl isocyanide dibromide 
• 3128-77-6 2-isocyanobiphenyl 

Downstream Products

• 23165-19-7 4,4-dimethylmorpholinium chloride 
• 3340-87-2 6-phenoxyphenanthridine 
• 832-68-8 6-aminophenanthridine 
• 130137-90-5 Phenanthridin-6-yl-(4-phenyl-furazan-3-yl)-amine 
• 82937-37-9 2-nitro-N-(phenanthridin-6-yl)aniline 
• 846-62-8 6-anilinophenanthridine 
• 66151-98-2 Phenanthridin-6-yl-m-tolyl-amine 
• 142138-63-4 Phenanthridin-6-yl-o-tolyl-amine 
• 78256-30-1 2-nitrophenanthridin-6(5H)-one 
• 23818-43-1 4-nitro-6(5H)-phenanthridinone 
• 144402-92-6 6-hydrazinophenanthridine 
• 23441-13-6 6-(4-methyl-piperazyl)-phenanthridine 
• 229-87-8 phenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 

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.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.

Application of phenanthridine compounds to pesticides

The invention relates to an application of phenanthridine compounds shown in general formula (1) to pesticides. Part of the compounds is used as a plant virus agent and can well inhibit the tobacco mosaic virus; when used as a bactericide, the compounds have good inhibitory activity on tomato early blight, wheat scab, potato late blight, phytophthora capsici, rape sclerotinia rot, cucumber gray mould, rice sheath blight disease, cucumber fusarium wilt, cercospora brown spot of peanut, apple ring rot, wheat sharp eyespot, corn southern leaf blight, watermelon anthracnose and rice bakanae disease; when used as an insecticide, the compounds have poisonous activity on armyworms, mosquito larvae, cotton bollworms, ostrinia nubilalis, aphids, adult mites and plutella xylostella. In the formula,when molecular nitrogen is not imine, R can represent hydrogen atoms, methyl, acetyl and benzoyl; R and R represent a hydrogen atom or an oxygen atom simultaneously; R and R can represent hydroxyl, acetoxyl, methoxyl, methyleneoxy, a fluorine atom and the hydrogen atom; R is a bromine atom or the fluorine atom; R is the hydrogen atom or vinyl. When nitrogen is imine, R doesnot represent any group; one of R and R does not represent any group, and the other can represent the hydrogen atom, methoxyl, ethyoxyl, benzyloxy and a chlorine atom; R, R, R and Rrepresent the hydrogen atom.

Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism

Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.

Synthesis method of 6-chlorophenanthridine

The invention belongs to the fields of synthesis of medicines and materials and in particular relates to a synthesis method of 6-chlorophenanthridine. The synthesis method comprises the following two steps: firstly, carrying out reaction on formic acid and acetic anhydride, then reacting with 2-aminobiphenyl to generate an intermediate I; and secondly, reacting the obtained intermediate I with chloride and lewis acid to obtain 6-chlorophenanthridine. The synthesis method provided by the invention has the advantages that operation for preparing 6-chlorophenanthridine is easier, and safety factor is high, so that the synthesis method is especially applicable to industrial production.

Organic electroluminescent materials and devices

Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting diode devices comprising these compounds are also described.

METAL COMPLEXES OF CYCLOMETALLATED IMIDAZO[1,2-f]PHENANTHRIDINE AND DIIMIDAZO[1,2-A:1',2'-C]QUINAZOLINE LIGANDS AND ISOELECTRONIC AND BENZANNULATED ANALOGS THEREOF

The present invention refers to-imidazo [1,2-f] the dee trillion which gets torn phenylphenanthridines and [1,2-a:1 ', 2' -c] quinazoline ligands, or its isoelectronic characteristic and or phosphor including analogue relates to compounds including metal complex. Furthermore, the present invention refers to these compounds including relates organic light emitting diode devices. (by machine translation)

Dinuclear cyclic metal iridium complex as well as preparation method and application thereof

The invention relates to a dinuclear cyclic metal iridium complex as well as a preparation method and application thereof. A chemical structure formula of the complex is shown in the description, wherein a form I and a form II shown in the description are bidentate ligands taking C and N atoms as ligand atoms and mutually independently have the following structures: formula I, formula II, formula III, formula IV, formula V, formula VI or formula VII shown in the description, wherein R is a hydrogen atom, alkyl, alkoxy, alkyl sulphanyl, alkyl amino, aryl, aryloxy, arylthio, aryl amino, aryl alkyl, aryl alkoxy, aryl alkyl sulphanyl, aryl alkyl amino, acyl, acyloxy, acylamino, imino or carboxyl; X is Cl, Br, I, PF6, BF4 or (CF3SO2)2N; n and m are mutually independently and are integers of 1 to 6. The dinuclear cyclic metal iridium complex is a single-excitation and double-emission phosphorescent probe, and absorption and luminescent properties of two phosphorescent groups are kept very well; the dinuclear cyclic metal iridium complex is hopeful to be used for phosphorescent ratio type O2 sensing and imaging, has relatively strong lipotropy and can be used for mitochondrial location.

Synthesis of helquats based on phenanthridinium units: Four-step procedure to novel extended helical dications

Three novel helical dications (helquats) containing phenanthridinium units have been synthesized from 6-(pyridin-2-ylethynyl)phenanthridine as a common precursor prepared by Sonogashira coupling of phenanthridin-6-yl triflate with 2-ethynylpyridine. Bisquaternization of the common precursor followed by rhodium-catalyzed [2+2+2] cycloisomerization led to the title helical dicationic scaffolds. The connectivity and spatial arrangement of the three target helquats were unambiguously established by X-ray crystal structure analysis.

Novel amide and sulphonamide derivatives of 6-(piperazin-1-yl)phenanthridine as potent Mycobacterium tuberculosis H37Rv inhibitors

A series of thirty three novel 6-(piperazin-1-yl)phenanthridine amide and sulphonamide analogues were synthesized, characterized and screened for their in vitro antimycobacterial activity against Mycobacterium tuberculosis (MTB) H37Rv strain. These compounds exhibited minimum inhibitory concentration (MIC) between >56 and 50 μg/mL. Out of these derivatives, few compounds 6l, 6r, 7b, 7f, 7g and 7k exhibited moderate activity (MIC = 6.25 μg/mL) and compounds 6b, 6e, 6k, 6n, 7h, 7i and 7n displayed good activity (MIC = 3.13 μg/mL), whereas compounds 6m, 6s and 7d exhibited excellent anti-tubercular activity (MIC = 1.56 μg/mL). In addition, MTT assay was accomplished on the active analogues of the series against mouse macrophage (RAW 264.7) cells to evaluate the toxicity profile of the newly synthesized compounds and selectivity index of the compounds was determined. Additionally, compounds 6b and 7d were docked to the ATPase domain of M. tuberculosis GyrB protein to know the interaction profile and structures of compounds 6b and 7d were further substantiated through single crystal XRD.