185129-91-3

Basic information

• Product Name: 2-(4-hydroxyphenyl)iMidazole[4,5f][1,10]phenanthroline
• Synonyms: 2-(4-hydroxyphenyl)iMidazole[4,5f][1,10]phenanthroline;2-(p-Hydroxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthrolline;Phenol, 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)-
• CAS NO: 185129-91-3
• Molecular Formula: C19H12N4O
• Molecular Weight: 312.32478
• Mol File: 185129-91-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-hydroxyphenyl)iMidazole[4,5f][1,10]phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-hydroxyphenyl)iMidazole[4,5f][1,10]phenanthroline(185129-91-3)
• EPA Substance Registry System: 2-(4-hydroxyphenyl)iMidazole[4,5f][1,10]phenanthroline(185129-91-3)

Safety Data

• Hazardous Substances Data: 185129-91-3(Hazardous Substances Data)

Usage

Molecular structure

A complex structure containing a phenanthroline ring linked to an imidazole ring with a 4-hydroxyphenyl group.

Usage in coordination chemistry

It has the ability to chelate with various metal ions, making it a popular compound in coordination chemistry and metal complexation studies.

Potential pharmaceutical applications

The compound can exhibit biological activity in the presence of certain metal ions, making it a potential candidate for drug development or as a ligand in metalloproteins.

Fluorescence probe

2-(4-hydroxyphenyl)imidazole[4,5-f][1,10]phenanthroline has been studied as a fluorescence probe for detecting metal ions in biological systems.

Analytical and diagnostic purposes

The compound's ability to form stable complexes with metal ions makes it useful for various analytical and diagnostic techniques.

Versatility

2-(4-hydroxyphenyl)imidazole[4,5-f][1,10]phenanthroline is a versatile compound with potential applications in various fields, particularly in coordination chemistry and bioinorganic chemistry.

Upstream product

• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 66-71-7 1,10-Phenanthroline 

Downstream Products

• 1352326-98-7 2-[4-[2-(1-piperidyl)ethoxy]phenyl]-1H-imidazo[4,5-f]-1,10-phenanthroline 
• 1352326-99-8 2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1H-imidazo[4,5-f]-1,10-phenanthroline 
• 1436591-01-3 4-[2-[4-(1H-imidazo[4,5-f]-1,10-phenanthrolin-2-yl)phenoxy]ethyl]morpholine 
• 1442692-00-3 C₂₅H₁₈ClN₄ORu⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

RETRACTED ARTICLE: Studies of proteasome inhibition and antitumor activity by novel amino acid-polypyridine-copper complexes

Five innovative ternary copper (II) complexes [Cu (OH-PIP)(Phe)Cl](1), [Cu (OH-PIP)(Gly)(H2O)]NO3·2H2O (2), [Cu (OH-PIP)(Ala)(Cl)]·H2O (3), [Cu (OH-PIP)(Met)]PF6·2H2O (4), and [Cu (OH-PIP)(Gln)(H2O)]Cl·3H2O (5) have been synthesized and characterized by infrared spectroscopy, elemental analysis, and single crystal X-ray diffraction analysis. X-ray crystallography showed that all Cu atoms were five-coordinated in a square-pyramidal configuration. They are screened for in vitro cytotoxicity against a panel of human cancer cell lines CAL-51, MDA-MB-231, HeLa, MCF-7, SGC-7901, A549, K562, and SMMC-7721. The most promising results were achieved for complexes 1 to 5, with the IC50 values in the range of 0.082μM to 0.69μM (against CAL-51 cell lines). The anticancer activities against CAL-51, MDA-MB-231, and MCF-7 were higher than that of Carboplatin. The mechanism studies showed that complexes 1 to 5 could inhibit proteasome activity, induce apoptosis, and inhibit cell proliferation, indicating their great potential as proteasome inhibitors for triple-negative breast cancer therapy.

Antibacterial activities and DNA-cleavage properties of novel fluorescent imidazo-phenanthroline derivatives

Design and biological activities of fluorescent imidazo-phenanthroline derivatives; (E)-5-((4-((4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenoxy)methyl)benzylidene)amino)- isophthalicacid, 2 and 2-(4-(((5-chloroquinolin-8-yl)oxy)methyl)phenyl)-1H-imidazo[4,5f] [1,10]phenanthroline, 3, have been reported. Their characterizations were performed by spectroscopic techniques. Their promising photophysical behaviours were observed in absorbance and fluorescence studies. The antibacterial activities of the compounds were determined against seven different microorganisms; Bacillus subtilis ATCC 6633(G + ), Pseudomonas aeruginosa ATCC 29853(G-), Escherichia coli ATCC 35,218 (G-), Enterococcus faecalis ATCC 292,112 (G + ), Salmonella typhimurium ST-10 (G-), Streptococcus mutans NCTC 10,449 (G + ), and Staphylococcus aureus ATCC 25923(G + ). MIC values of 3 was determined as 156,25 μM on all tested bacteria. A preliminary study of the structure–activity relationship (SAR) also revealed that the antimicrobial activity depended on the substituents on the phenyl ring. The electron withdrawing Cl-substitued compound 3 most favour for antimicrobial activity even at lowest concentration compared to other compounds. DNA-cleavage activities of the compounds were also investigated. The interactions of the compounds with supercoiled pBR322 plasmid DNA were obtained by agarose gel electrophoresis. All imidazo-phenanthroline derivatives were found to be highly effective on DNA, even at the lowest concentrations because of their planar nature which provides ease of bind to the helix structure of DNA.

Luminescent heteroleptic Eu(iii) probes for the selective detection of diethyl chlorophosphate as a G-series nerve agent mimic in the vapor phase using solid-state films

The extreme toxicity of innocuous organophosphate (OP) nerve agents poses a significant public health risk. Developing an efficient sensing and detection system is crucial to contain and mitigate disasters and strengthen national security. Luminescence sp

Preparation of Different Substitued Polypyridine Ligands, Ruthenium(II)-Bridged Complexes and Spectoscop?c Studies

Novel different substitued polypyridine ligands 4-((4-(1H-imidazo[4,5-f][1,10]phenanthroline-2-yl)phenoxy)methyl)benzaldehyde (BA-PPY), (E)-N-(4-((4-(1H-imidazo[4,5-f][1,10]phenanthroline-2-yl)phenoxy)methyl)benzylidene)-pyrene-4-amine (PR-PPY), (E)-N-(4-

Novel Copper Complexes That Inhibit the Proteasome and Trigger Apoptosis in Triple-Negative Breast Cancer Cells

Five innovative ternary copper(II) complexes [Cu(OH-PIP)(Phe)Cl](1), [Cu(OH-PIP)(Gly)(H2O)]NO3·2H2O (2), [Cu(OH-PIP)(Ala)(Cl)]·H2O (3), [Cu(OH-PIP)(Met)]PF6·2H2O (4), and [Cu(OH-PIP)(Gln)(H

Synthesis, characterization, and nonlinear optical responses of nickel(ii) complexes with phenanthroline-based ligands

Three nickel(II) complexes with phenanthroline-based ligands were synthesized and characterized by UV-visible, IR, MS, and elemental analysis. Their off-resonance third-order nonlinear optical (NLO)properties were measured using a femtosecond laser and th

A Gyroidal MOF with Unprecedented Interpenetrating utc-c Network Exhibiting Exceptional Thermal Stability and Ultrahigh CO2 Affinity

A zeolite-like gyroidal MOF (denoted as SCNU-1) constructed with Cu ions and 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol has a featured interpenetrating uninodal utc-c network which is for the first time found in the real structure. Moreover, SCNU

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.

In-vitro and in-vivo monitoring of gold(III) ions from intermediate metabolite of sodium aurothiomalate through water-soluble ruthenium (II) complex-based luminescent probe

Real-time monitoring of drug metabolism in vivo is of great significance to drug development and toxicology research. The purpose of this study is to establish a rapid and visual in vivo detection method for the detection of an intermediate metabolite of the gold (I) drug. Gold (I) drugs such as sodium aurothiomalate (AuTM) have anti-inflammatory effects in the treatment of rheumatoid arthritis. Gold(III) ions (Au3+) are the intermediate metabolite of gold medicine, and they are also the leading factor of side effects in the treatment of patients. However, the rapid reduction of Au3+ to Au+ by thiol proteins in organisms limits the in-depth study of metabolism of gold drugs in vivo. Here we describe a luminescence Au3+ probe (RA) based on ruthenium (II) complex for detecting Au3+ in vitro and in vivo. RA with large Stokes shift, good water solubility and biocompatibility was successfully applied to detect Au3+ in living cells and vivo by luminescence imaging, and to trap the fluctuation of Au3+ level produced by gold (I) medicine. More importantly, the luminescent probe was used to the detection of the intermediate metabolites of gold (I) drugs for the first time. Overall, this work offers a new detection tool/method for a deeper study of gold (I) drugs metabolite.

Diatom-like silica–protein nanocomposites for sustained drug delivery of ruthenium polypyridyl complexes

Inspired by the unique glass cell wall of diatom, we design a new nanostructure of human serum albumin nanoparticle (HSANP) coated with silica (HSA/SiO2), which consists of a core–satellite assembly of small silica nanoparticles on a single HSA