4552-43-6

Basic information

• Product Name: 4-CHLORO-2-CYANOQUINOLINE
• Synonyms: 4-CHLORO-2-CYANOQUINOLINE;4-chloroquinoline-2-carbonitrile
• CAS NO: 4552-43-6
• Molecular Formula: C₁₀H₅ClN₂
• Molecular Weight: 188.6131
• Mol File: 4552-43-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 320.4°Cat760mmHg
• Flash Point: 147.6°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 0.000319mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CHLORO-2-CYANOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-CYANOQUINOLINE(4552-43-6)
• EPA Substance Registry System: 4-CHLORO-2-CYANOQUINOLINE(4552-43-6)

Safety Data

• Hazardous Substances Data: 4552-43-6(Hazardous Substances Data)

Usage

Preparation

synthesis of 4-chloroquinoline-2-carbonitrile: To a solution of 2,4-dichloroquinoline (444 mg, 2.24 mmol) in DMF (5 mL) was added zinc cyanide (117 mg, 1.14 mmol) and Pd(PPh3)4 (259 mg, 0.22 mmol). The reaction mixture was stirred at 120 °C for 1 h. A saturated NH4Cl solution (20 mL) was added and the mixture was extracted with ethyl acetate (3x5 mL). The organic layer was washed with a NaCl solution (5mL) and dried over sodium sulfate, filtered and evaporated. The product was further purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (95:5) to give 4-chloroquinoline-2-carbonitrile (392 mg, 2.085 mmol, 93 %) as a white solid.

InChI:InChI=1/C10H5ClN2/c11-9-5-7(6-12)13-10-4-2-1-3-8(9)10/h1-5H

Upstream product

• 4637-59-6 4-Chloroquinoline N-oxide 
• 151-50-8 potassium cyanide 
• 56-57-5 4-nitroquinoline-N-oxide 
• 2942-58-7 diethyl cyanophosphonate 
• 20473-16-9 4-chloro-2-cyanoquinoline 1-oxide 
• 611-35-8 4-chloroquinoline 
• 330660-35-0 silver cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 557-21-1 zinc(II) cyanide 
• 703-61-7 2,4-dichloroquinoline 

Downstream Products

• 15733-82-1 2-carboxy-4-chloroquinoline 

Relevant articles and documents

Enantioselective Palladium(II)-Catalyzed Oxidative Aminofluorination of Unactivated Alkenes with Et4NF?3 HF as a Fluoride Source

The first asymmetric PdII-catalyzed aminofluorination of unactivated alkenes using chiral quinoline-oxazolines (Quox) as ligands has been developed. This reaction provides easy access to a wide array of enantiomerically enriched β-fluoropiperidines in good yields and with excellent enantioselectivity. Notably, Et4NF?3 HF as a readily accessible nucleophilic fluoride source was found to play an essential role in the enantioselective control, and CsOCF3 also acts a key additive to improve the excellent ee value of products.

Cyclic bridged analogs of isoCA-4: Design, synthesis and biological evaluation

In this work, a series of cyclic bridged analogs of isocombretastatin A-4 (isoCA-4) with phenyl or pyridine linkers were designed and synthesized. The synthesis of the desired analogs was performed by the formation of nitro-vinyl intermediates, followed by a Cadogan cyclization. Structure activity relationship (SAR) study demonstrates the critical role of the combination of quinaldine as ring A, pyridine as the linker, and indole as ring B in the same molecule, for the cytotoxic activity. Among all tested compounds, compound 42 showed the highest antiproliferative activity against a panel of cancer cell lines with average IC50 values of 5.6 nM. Also, compound 42 showed high antiproliferative activity against the MDR1-overexpressing K562R cell line; thus, it was 1.5- and 12-fold more active than the reference compounds, isoCA-4 and CA-4, respectively. Moreover, 42 displayed a strong antiproliferative activity against the colon-carcinoma cells (HT-29), which are resistant to combretastatin A-4 and isoCA-4, and it was found to be 8000-fold more active than natural CA-4. Compound 42 also effectively inhibited tubulin polymerization both in vitro and in cells, and induced cell cycle arrest in G2/M phase. Next, we demonstrated that compound 42 dose-dependently caused caspase-induced apoptosis of K562 cells through mitochondrial dysfunction. Finally, we evaluated the effect of compound 42 in human no cancer cells compared to the reference compound. We demonstrated that 42 was 73 times less cytotoxic than isoCA-4 in quiescent peripheral blood lymphocytes (PBLs). In summary, these results suggest that compound 42 represents a promising tubulin inhibitor worthy of further investigation.

Quinoline substituted indole compound, and preparation method and application thereof

The invention discloses a quinoline substituted indole compound, a pharmaceutical composition containing the quinoline substituted indole compound, and a preparation method for the quinoline substituted indole compound. The invention also discloses the quinoline substituted indole compound, a pharmaceutical application for the pharmaceutical composition containing the quinoline substituted indolecompound, specifically an application of the pharmaceutical composition containing the quinoline substituted indole compound in preparation of drugs used for treatment of tumors, and an application ofthe quinoline substituted indole compound in preparation of drugs used for treatment of diseases or symptoms by inhibition of tubulin activity.