5278-87-5

Basic information

• Product Name: 2-phenylbenzo[h]quinoline-4-carboxylic acid
• CAS NO: 5278-87-5
• Molecular Formula: C₂₀H₁₃NO₂
• Molecular Weight: 299.3227
• Mol File: 5278-87-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 543.2°C at 760 mmHg
• Flash Point: 282.3°C
• Density: 1.308g/cm³
• Vapor Pressure: 1.25E-12mmHg at 25°C
• Refractive Index: 1.732
• CAS DataBase Reference: 2-phenylbenzo[h]quinoline-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylbenzo[h]quinoline-4-carboxylic acid(5278-87-5)
• EPA Substance Registry System: 2-phenylbenzo[h]quinoline-4-carboxylic acid(5278-87-5)

Safety Data

• Hazardous Substances Data: 5278-87-5(Hazardous Substances Data)

Upstream product

• 134-32-7 1-amino-naphthalene 
• 100-52-7 benzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 5353-96-8 6,7-benzoisatin 
• 98-86-2 acetophenone 

Downstream Products

• 854047-28-2 ethyl 2-phenylbenzo[h]quinoline-4-carboxylate 
• 65-85-0 benzoic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of novel benzo- and tetrahydrobenzo-[h]quinoline derivatives as potential DNA-intercalating antitumor agents

A new series of benzo- and tetrahydro benzo-[h]quinoline bearing a flexible (dimethylamino)ethylcarboxamide side chain was designed and synthesized as DNA-intercalating antitumor agents. The cytotoxic activity of the synthesized compounds was evaluated against four human cancer cell lines including MCF-7, A2780, C26 and A549. In general, saturated quinolines (tetrahydrobenzo[h]quinolines) exhibited more cytotoxicity compared to their corresponding unsaturated quinolines (benzo[h]quinolines). Compound 6e showed significant cytotoxicity against all four human cancer cell lines with IC50 values ranging from 1.86 to 3.91 μM. The interaction of the selected compounds showed significant cytotoxicity (6b, 6e, 6i and 6j) with calf thymus DNA (CT-DNA) was studied by UV and florescent spectroscopy. In general, benzo[h]quinolines showed higher interacting effect with DNA than their corresponding saturated tetrahydrobenzo[h]quinolines. Compound 6i exhibited the most DNA intercalating effects among the series. The apoptotic induction potential of the most cytotoxic compounds (6e, 6b and 6i) in A549 cells was studied using Annexin V-FITC/Propidium iodide staining assay. Compound 6e which showed the most cytotoxic effect against A549 cancer cells also exhibited stronger apoptotic induction activity in comparison with 6b and 6i.The docking was performed in order to study the DNA interaction properties of these compounds. According to the computational data, these compounds can interact with DNA as DNA-intercalating agents.

Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5′-phosphatase (SHIP)

Recently, inhibition of the SH2-containing inositol 5′-phosphatase 1 (SHIP1) has become an attractive strategy for facilitating engraftment of MHC-I mismatched bone marrow grafts, increasing the number of adult stem cells in vivo, and inducing mobilization of hematopoietic stem cells. Utilizing high-throughput screening, two quinoline small molecules (NSC13480 and NSC305787) that inhibit SHIP1 enzymatic activity were discovered. New syntheses of these inhibitors have been developed which verified the relative stereochemistry of these structures. Utilizing this synthetic route, some analogs of these quinolines have been prepared and tested for their ability to inhibit SHIP. These structure activity studies determined that an amine tethered to the quinoline core is required for SHIP inhibition. SHIP inhibition may explain the antitumor effects of similar quinoline amino alcohols and provides an impetus for further synthetic studies in this class of compounds.