120085-99-6

Basic information

• Product Name: 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline
• Synonyms: 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline
• CAS NO: 120085-99-6
• Molecular Formula: C₂₆H₁₆N₂O₂
• Molecular Weight: 388.41744
• Mol File: 120085-99-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 657.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.303±0.06 g/cm3(Predicted)
• PKA: 3.86±0.30(Predicted)
• CAS DataBase Reference: 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline(120085-99-6)
• EPA Substance Registry System: 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline(120085-99-6)

Safety Data

• Hazardous Substances Data: 120085-99-6(Hazardous Substances Data)

Usage

General Description

2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline is a chemical compound with complex and long structure of aromatic rings and formyl groups. It is commonly used as a ligand in coordination chemistry and metal complexes due to its ability to chelate metal ions. 2,9-bis[p-(formyl)phenyl]-1,10-phenanthroline has the potential to form stable complexes with various transition metals, making it valuable in catalytic and medicinal applications. It can also exhibit fluorescence properties, making it useful in the development of fluorescent probes and sensors for biochemical and environmental analysis. Additionally, its chemical structure and properties make it a valuable tool in the field of materials chemistry, nanotechnology, and organic synthesis.

Upstream product

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• 157523-10-9 2,9-Bis<(p-tetrahydropyranyloxymethyl)phenyl>-1,10-phenanthroline 
• 157523-08-5 2-<(p-Tetrahydropyranyloxymethyl)phenyl>-1,10-phenanthroline 
• 17100-68-4 2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran 
• 105114-53-2 1-bromo-4-(5,5-dimethyl-1,3-dioxan-2-yl)benzene 
• 66-71-7 1,10-Phenanthroline 
• 321697-17-0 2,9-bis[p-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-1,10-phenanthroline 
• 157523-11-0 2,9-bis(p-hydroxymethylphenyl)-1,10-phenanthroline 
• 120085-98-5 2,9-bis(4-(dibromomethyl)phenyl)-1,10-phenanthroline 
• 2417-95-0 p-tolyllithium 

Downstream Products

• 157523-12-1 2,9-Bis(p-carboxyphenyl)-1,10-phenanthroline 

Relevant articles and documents

Design, synthesis, and antiproliferative effect of 2,9-bis[4-(pyridinylalkylaminomethyl)phenyl]-1,10-phenanthroline derivatives on human leukemic cells by targeting G-quadruplex

Current multiagent chemotherapy regimens have improved the cure rate in acute leukemia patients, but they are highly toxic and poorly efficient in relapsed patients. To improve the treatment approaches, new specific molecules are needed. The G-quadruplexes (G4s), which are noncanonical nucleic acid structures found in specific guanine-rich DNA or RNA, are involved in many cellular events, including control of gene expression. G4s are considered as targets for the development of anticancer agents. Heterocyclic molecules are well known to target and stabilize G4 structures. Thus, a new series of 2,9-bis[(substituted-aminomethyl)phenyl]-1,10-phenanthroline derivatives (1a–i) was designed, synthesized, and evaluated against five human myeloid leukemia cell lines (K562, KU812, MV4-11, HL60, and U937). Their ability to stabilize various oncogene promoter G4 structures (c-MYC, BCL-2, and K-RAS) as well as the telomeric G4 was also determined through the fluorescence resonance energy transfer melting assay and native mass spectrometry. In addition, the more bioactive ligands 1g–i were tested for telomerase activity in HuT78 and MV4-11 protein extracts.

Design, Synthesis, and Evaluation of 2,9-Bis[(substituted-aminomethyl)phenyl]-1,10-phenanthroline Derivatives as G-Quadruplex Ligands

Genomic sequences able to form guanine quadruplexes (G4) are found in oncogene promoters, in telomeres, and in 5′- and 3′-untranslated regions as well as introns of messenger RNAs. These regions are potential targets for drugs designed to treat cancer. Herein, we present the design and syntheses of ten new phenanthroline derivatives and characterization of their interactions with G4-forming oligonucleotides. We evaluated ligand-induced stabilization and specificity and selectivity of ligands for various G4 conformations using FRET-melting experiments. We investigated the interaction of compound 1 a (2,9-bis{4-[(3-dimethylaminopropyl)aminomethyl]phenyl}-1,10-phenanthroline), which combined the greatest stabilizing effect and specificity for G4, with human telomeric sequences using FRET, circular dichroism, and ESI-MS. In addition, we showed that compound 1 a interferes with the G4 helicase activity of Saccharomyces cerevisiae Pif1. Interestingly, compound 1 a was significantly more cytotoxic toward two human leukemic cell lines than to normal human blood mononuclear cells. These novel phenanthroline derivatives will be a starting point for further development and optimization of potent G4 ligands that have potential as anticancer agents.

COVALENT ORGANIC FRAMEWORKS WITH A WOVEN STRUCTURE

The disclosure provides for covalent organic frameworks (COFs) that constructed from weaving a plurality of long organic threads together. In particular, the disclosure provides for the construction of woven COFS, where long organic strands are connected