219615-30-2

Basic information

• Product Name: 2-(2-N,N'-DiMethylaMinophenyl)iMidazole[4,5f][1,10]phenanthroline
• Synonyms: 2-(2-N,N'-DiMethylaMinophenyl)iMidazole[4,5f][1,10]phenanthroline
• CAS NO: 219615-30-2
• Molecular Formula: C21H17N5
• Molecular Weight: 339.39
• Mol File: 219615-30-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-N,N'-DiMethylaMinophenyl)iMidazole[4,5f][1,10]phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-N,N'-DiMethylaMinophenyl)iMidazole[4,5f][1,10]phenanthroline(219615-30-2)
• EPA Substance Registry System: 2-(2-N,N'-DiMethylaMinophenyl)iMidazole[4,5f][1,10]phenanthroline(219615-30-2)

Safety Data

• Hazardous Substances Data: 219615-30-2(Hazardous Substances Data)

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 1442691-99-7 C₂₇H₂₃ClN₅Ru⁽¹⁺⁾*Cl^(1-) 
• 928625-35-8 PtCl₂C₁₂H₆N₂CN₂HC₆H₄N(CH₃)2 

Relevant articles and documents

Luminescent pH sensors based on Ru(bpy)2L2+ where L are imidazo[f]1,10-phenanthrolines

The luminescence quantum yield of Ru(bpy)2L2+ complexes where L are imidazo[f]1,10-phenanthrolines is strongly controlled by pH due to intramolecular photoinduced electron transfer.

Synthesis, characterization, DNA binding, light switch "on and off", docking studies and cytotoxicity, of ruthenium(II) and cobalt(III) polypyridyl complexes

The novel ligand (dmbip) 2-(4-N, N-dimethylbenzenamine)1H-imidazo[4, 5-f][1, 10]phenanthroline and its complexes [Ru(phen)2dmbip] 2+ (1), [Ru(bpy)2dmbip]2+ (2), [Co(phen) 2dmbip]3+ (3) and

Luminescent ruthenium(II)-para-cymene complexes of aryl substituted imidazo-1,10-phenanthroline as anticancer agents and the effect of remote substituents on cytotoxic activities

Ruthenium complexes are currently significant attention in medicinal chemistry as they offer various properties which make them an appropriate choice for drug development. Herein, a series of ruthenium(II)-p-cymene-2-aryl-imidazo-1,10-phenanthroline derivatives have been prepared and characterised by elemental analysis, infrared, LC-mass and NMR techniques. The structural and chemical properties shows that Ru(II) complexes have got rigidity, planarity, aromaticity, hydrogen donating and accepting capability which aids both solubility and interaction with biomolecules. The binding strength of these complexes with DNA and BSA were found to be 104–106 M?1. The competitive displacement of ethidium bromide (EtBr) from DNA in the presence of complex reveals an intercalation or groove binding further this was supported by viscosity and in-silico studies. The cytotoxicity study of these Ru(II) complexes were conducted with two cancer cell lines (MDA-MB-231 and HeLa) and one human embryonic kidney cells (HEK-293). The study revealed that [(η6-p-cymene)RuCl (κ2-N,N-2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]Phenanthroline].PF6 (4e), [(η6-p-cymene)RuCl(κ2-N,N-2-(4-bromophenyl)-1H-imidazo[4,5-f][1,10]Phenanthroline].PF6 (4f) and [(η6-p-cymene)RuCl(κ2-N,N-2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]Phenanthro line].PF6 (4g) were found exhibit least inhibitory concentration (IC50) and high selectivity with respect to HeLa and MDA-MB-231. The activity of the Ru(II) complexes were position and substituents dependent.

Phenanthroimidazole derivatives act as potent inducer of autophagy by activating DNA damage pathway

A series of imidazo[4,5f][1,10]phenanthroline derivatives (1–6) have been synthesized in this study, and their inhibitory activity was evaluated by MTT assay. Results showed that all of these compounds demonstrate a promising inhibitory activity against a panel of human cancer cell lines. The 6, the most effective compound with IC50 of approximately 2.3 ± 0.1 μM, was against the growth and could induce autophagy of HepG2 cells. This condition was confirmed by abundant autophagic vacuoles appearing in cells and evident ultrastructural changes observed under transmission electron microscopy. The autophage induced by 6 has also been demonstrated by up-regulating LC3-II and Beclin1. The apoptosis and G2/M phase cell cycle arrest through DSB damage have also been confirmed after the HepG2 cells were treated by 6. These multiple effects, especially induction apoptosis and autophagy, indicate the potential of 6 for development as a novel anticancer drug.

2,4,5-Triaryl imidazole probes for the selective chromo-fluorogenic detection of Cu(II). Prospective use of the Cu(II) complexes for the optical recognition of biothiols

The sensing behaviour toward metal cations and biothiols of two 2,4,5-triarylimidazole probes (3a and 3b) is tested in acetonitrile and in acetonitrile–water. In acetonitrile the two probes present charge-transfer absorption bands in the 320–350 nm interv

Intramolecular electron transfer in Cu(ii) complexes with aryl-imidazo-1,10-phenanthroline derivatives: experimental and quantum chemical calculation studies

1H-Imidazo[4,5-f][1,10]phenanthrolines containing phenyl (1), 4-(N,N-dimethylamino)phenyl (2), 4-(azadithiacrown-ether)phenyl (3), 3,4-dimethoxyphenyl (4) and 2,2′-bithiophen-5-yl (5) were synthesized and their Cu(ii) complexes were studied to determine the effect of substituents, geometry of complexes and solvent nature on the spectral and redox properties of the copper complexes. It was found that in the case of 4-(N,N-dimethylamino)phenyl- and 4-(azadithiacrown-ether)phenyl substituents, the formation of a L2·Cu2+ complex of pseudo-tetrahedral geometry causes the appearance of an intense metal-to-ligand charge transfer (MLCT) band in the visible region and induces a positive shift in the reduction potential causing the occurrence of autoreduction of Cu(ii). Density functional theory (DFT) and its extension to time dependent density functional theory (TD-DFT) were employed to study the molecular structure and electronic and spectroscopic properties of copper with the 4-(N,N-dimethylamino)phenyl-1H-imidazo[4,5-f][1,10]phenanthroline ligand (2). The calculation results are in agreement with those obtained from optical measurements. Electrochemical studies showed that the autoreduction is observed when Cu2+/Cu+ transfer and oxidation of the ligand occur under the closed electrochemical condition.

Red-emitting cyclometalated platinum(II) complexes with imidazolyl phenanthrolines: Synthesis and photophysical properties

Three cyclometalated platinum(II) complexes with substituted imidazolyl phenanthrolines L1–L3 have been synthesized and characterized using spectral and electrochemical techniques. The effect of substituent (in the appended aromatic ring to the imidazolyl moiety) on the electronic feature and redox potential of the cyclometalated platinum(II) complexes of general formula [Pt(ppy)(L1-L3)]Cl (1–3) are discussed. Complexes 1–3 are luminescent in the solution and solid state. Complex 1, with two trifluoromethyl moieties present in the ligand shows a higher degree of PtII?PtII interaction than the ligand incorporated with N,N-dimethyl moiety. The excimer formation through π ? π and d ? π (Pt?Pt) interactions is evident and the degree of excimer formation is in the order 1 >2 > 3. Excited-state properties are corroborated by static and time-dependent density-functional theory.

HETEROAROMATIC IMIDAZOLYL COMPOUNDS AND METHODS FOR TREATING CANCER

Provided herein are heteroaromatic imidazolyl compounds, compositions comprising such compounds, and related methods of making and using the compounds, e.g., the compounds are useful for treating diseases such as cancer.

Microwave-assisted synthesis of arene ruthenium(II) complexes that induce S-phase arrest in cancer cells by DNA damage-mediated p53 phosphorylation

A series of arene ruthenium(II) complexes coordinated by phenanthroimidazole derivates, [(C6H6)Ru(L)Cl] Cl·2H2O (1b L = IP, 2b L = p-NMe2PIP, 3b L = p-MeOPIP, 4b L = p-HOPIP, 5b L = p-COOHPIP, 6b L = p-CF3

Potassium ferro-cyanide trihydrate complex catalyzed one-pot synthesis of 2-phenylimidazo [4,5-f] [1,10] phenanthroline

Various 2-phenylimidazo [4,5-f] [1,10] phenanthrolines were synthesized from potassium ferro-cyanide trihydrate (KFCT) complex catalyzed three component reaction of 1,10-phenanthroline-5,6-dione, aromatic aldehydes and ammonium acetate at room temperature in excellent isolated yield. This is a simple and straight forward, high yielding, not involving any hazardous or expensive catalyst method.