185129-90-2

Basic information

• Product Name: 2-(4-chlorophenyl)iMidazole[4,5f][1,10]phenanthroline
• Synonyms: 2-(4-chlorophenyl)iMidazole[4,5f][1,10]phenanthroline
• CAS NO: 185129-90-2
• Molecular Formula: C₁₉H₁₁ClN₄
• Molecular Weight: 330.77
• Mol File: 185129-90-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-chlorophenyl)iMidazole[4,5f][1,10]phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)iMidazole[4,5f][1,10]phenanthroline(185129-90-2)
• EPA Substance Registry System: 2-(4-chlorophenyl)iMidazole[4,5f][1,10]phenanthroline(185129-90-2)

Safety Data

• Hazardous Substances Data: 185129-90-2(Hazardous Substances Data)

Upstream product

• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 66-71-7 1,10-Phenanthroline 
• 1073-67-2 4-vinylbenzyl chloride 
• 79790-36-6 9,10-diamino-1,4,5,8-tetraazaphenanthrene 
• 106-43-4 para-chlorotoluene 
• 873-76-7 para-Chlorobenzyl alcohol 

Relevant articles and documents

Liposomes encapsulated iridium(III) polypyridyl complexes enhance anticancer activity in vitro and in vivo

Three iridium(III) complexes [Ir(ppy)2(CPIP)](PF6) (Ir-1, ppy = 2-phenylpyridine, CPIP = 2-(4-chlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), [Ir(ppy)2(DCPIP)](PF6) (Ir-2, DCPIP = 2-(3,4-dichlorophenyl)-1H

Towards the Development of Photo-Reactive Ruthenium(II) Complexes Targeting Telomeric G-Quadruplex DNA

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Targeting G-Rich DNA Structures with Photoreactive Bis-Cyclometallated Iridium(III) Complexes

The synthesis and characterisation of three novel iridium(III) bis-cyclometallated complexes is reported. Their photophysics have been fully characterised by classical methods and revealed charge-transfer (CT) and ligand-centred (LC) transitions. Their ability to selectively interact with G-quadruplex telomeric DNA over duplex DNA has been studied by circular dichroism (CD), bio-layer interferometry (BLI) and surface plasmon resonance (SPR) analyses. Interestingly, one of the complexes was able to promote photoinduced electron transfer (PET) with the guanine DNA base, which in turn led to oxidative damage (such as the formation of 8-oxoguanine) to the telomeric sequence. To the best of our knowledge, this is the first study of highly photo-oxidising bis-cyclometallated iridium(III) complexes with G-quadruplex telomeric DNA.

A Remote ‘Imidazole’-Based Ruthenium(II) Para-Cymene Pre-catalyst for the Selective Oxidation Reaction of Alkyl Arenes and Alcohols

Herein we disclosed the use of a remote ‘imidazole’-based precatalyst [(para-cymene)RuII(L)Cl]+, C-1 where L=2-(4-substituted-phenyl)-1H-imidazo[4,5-f][1,10] phenanthroline) for the selective oxidation of a variety of alkyl arenes/heteroarenes and alcohols to their corresponding aldehydes or ketones in presence of tert-butyl hydroperoxide (TBHP). The remote ‘imidazole’ moiety present in the complex facilitates the activation of oxidant and subsequent generation of active species via the release of para-cymene from C-1, which in-turn was less effective without the ‘imidazole’ moiety. The mechanistic features of C-1 promoted oxidation of alkyl arenes were also assessed from spectroscopic, kinetic, and few control experiments. The substrate scope for C-1 promoted oxidation reaction was assessed based on the selective oxidation of 27-different alkyl arenes/heteroarenes and 25 different alcohols to their corresponding aldehydes/ketones in moderate to good yields.

Synthesis, docking studies and antitumor activity of phenanthroimidazole derivatives as promising c-myc G-quadruplex DNA stabilizers

Phenanthroimidazole derivatives containing phenanthroline and imidazole heterocyclic aromatic rings are effective agents to inhibit tumor cell growth. Herein, halogen element-modified imidazo[4,5f][1,10]phenanthroline derivatives 1–6 (1, 4-fluorophenyl; 2

Remote ‘Imidazole’ Based Ruthenium(II) p-Cymene Precatalyst for Selective Oxidative Cleavage of C?C Multiple Bonds

The dual role of remote ‘imidazole’ attached with the precatalyst [(p-cymene)RuII(L)Y]+ (L=2-(4-substituted-phenyl)-1H-imidazo[4,5-f][1,10] phenanthroline, Y=chloride/solvent) was explored for the selective oxidative cleavage of C?C multiple bonds to acetals/aldehydes. The presence of ‘imidazole’ in the precatalysts was found to be useful for the activation of oxidant and release of p-cymene from the precatalysts, which in turn was not effective without the ‘imidazole’ moiety. The mechanistic aspects of the precatalyst were evaluated from spectroscopic, kinetic, and few other controlled experiments. The loss of p-cymene is the key step for the reaction and found to be faster in solvated precatalyst, [(p-cymene)RuII(L)(MeOH)]++ and thus showed 3–4-fold more effective as compared to [(p-cymene)RuII(L)Cl]+.

Oxovanadium phenanthroimidazole derivatives: synthesis, DNA binding and antitumor activities

Four unsymmetrical oxovanadium phenanthroimidazole complexes, [VO(hntdtsc)(NPIP)] (1), [VO(hntdtsc)(CPIP)] (2), [VO(hntdtsc)(MEPIP)] (3) and [VO(hntdtsc)(HPIP)] (4) (hntdtsc?=?2-hydroxy-1-naphthaldehyde thiosemicarbazone, NPIP?=?2-(4-nitrophenyl)-imidazo[

Arene Ruthenium(II) Complexes as Low-Toxicity Inhibitor against the Proliferation, Migration, and Invasion of MDA-MB-231 Cells through Binding and Stabilizing c-myc G-Quadruplex DNA

Arene Ru(II) complexes have long been extensively studied as potential inhibitors against the proliferation of tumor cells, but their behavior against the migration and invasion of tumor cells needs further research. In this work, a series of arene Ru(II) complexes, (η6-C6H6)Ru(p-XPIP)Cl]Cl (X = H, 1; F, 2; Cl, 3; Br, 4; and I, 5), have been synthesized, and their inhibitory activity against the migration and invasion of MDA-MB-231 breast cancer cells have been investigated. It is found that all of these complexes exhibit excellent inhibitory activity (IC50) against the growth of MDA-MB-231 breast cancer cells, and the value of IC50 for 1, 2, 3, 4, and 5 is about >300, 52.6, 11.4, 45.5, and 59.1 μM, respectively. Further studies by wound-healing assay, FITC-geltain assay, and flow cytometry assay showed that 3 can apparently suppress the migration and invasion of MDA-MB-231 cells via the joint action of S-phase arrest and apoptosis. Moreover, the binding behavior of these arene Ru(II) complexes with c-myc G-quadruplex DNA has also been studied, and the results showed that these complexes can bind and stabilize c-myc G-quadruplex DNA in groove binding mode. Also, the low toxicity of 3 was confirmed by its low inhibitory activity against the growth of normal MCF-10A breast cells in vitro and the development of zebrafish embryos in vivo. In other words, these results indicated that synthetic arene Ru(II) complexes can be developed as low-toxicity agents against the proliferation, migration, and invasion of breast cancer cells.

Imidazo [4,5f][1,10] phenanthroline derivatives as inhibitor of c-myc gene expression in A549 cells via NF-κB pathway

1,10-Phenanthroline has been shown to exhibit anticancer activity. Here, a series of imidazo [4,5f][1,10] phenanthroline derivatives 1-10 were synthesized and their biological activities were further elucidated. We found that 2-(4-Brominephenyl)-imidazo [