158583-91-6

Usage

Derived from

Quinoline

Contains

Two chlorine atoms

Contains

A carbonitrile group attached to the third carbon atom of the quinoline ring

Usage

As a building block in the synthesis of pharmaceuticals and agrochemicals

Potential applications

Development of antimalarial drugs and other biologically active compounds

Also used as

An intermediate in organic synthesis for the preparation of various heterocyclic compounds.

InChI:InChI=1/C10H4Cl2N2/c11-8-2-1-6-3-7(5-13)10(12)14-9(6)4-8/h1-4H

Upstream product

• 108-42-9 3-chloro-aniline 
• 588-07-8 3-Chloroacetanilide 
• 73568-33-9 2,7-dichloro-quinoline-3-carbaldehyde 

Downstream Products

• 1415354-65-2 1-benzyl-8-chloro-1H-pyrimido[4,5-b]quinolin-4-one 
• 1415354-72-1 2-(benzylamino)-7-chloroquinoline-3-carbonitrile 

Relevant academic research and scientific papers

Synthesis and Evaluation of the Antibacterial and Antioxidant Activities of Some Novel Chloroquinoline Analogs

Quinoline heterocycle is a useful scaffold to develop bioactive molecules used as anticancer, antimalaria, and antimicrobials. Inspired by their numerous biological activities, an attempt was made to synthesize a series of novel 7-chloroquinoline derivati

lH-Pyrazolo[3,4-b]quinolin-3-amine derivatives inhibit growth of colon cancer cells via apoptosis and sub G1 cell cycle arrest

A series of lH-pyrazolo[3,4-b]quinolin-3-amine derivatives were synthesized and evaluated for anticancer efficacy in a panel of ten cancer cell lines, including breast (MDAMB-231 and MCF-7), colon (HCT-116, HCT-15, HT-29 and LOVO), prostate (DU-145 and PC3), brain (LN-229), ovarian (A2780), and human embryonic kidney (HEK293) cells, a non-cancerous cell line. Among the eight derivatives screened, compound QTZ05 had the most potent and selective antitumor efficacy in the four colon cancer cell lines, with IC50 values ranging from 2.3 to 10.2 μM. Furthermore, QTZ05 inhibited colony formation in HCT-116 cells in a concentration-dependent manner. Cell cycle analysis data indicated that QTZ05 caused an arrest in the sub G1 cell cycle in HCT-116 cells. QTZ05 induced apoptosis in HCT-116 cells in a concentration-dependent manner that was characterized by chromatin condensation and increase in the fluorescence of fluorochrome-conjugated Annexin V. The findings from our study suggest that QTZ05 may be a valuable prototype for the development of chemotherapeutics targeting apoptotic pathways in colorectal cancer cells.

Base-catalyzed cyclization reaction of 2-chloroquinoline-3-carbonitriles and guanidine hydrochloride: A rapid synthesis of 2-amino-3H-pyrimido[4,5-b] quinolin-4-ones

t-BuOK-catalyzed cyclization of 2-chloroquinoline-3-carbonitriles with guanidine hydrochloride provided simple and rapid synthesis of 2-amino-3H-pyrimido[4,5-b]quinolin-4-ones in very short reaction time with good yield. Other 1,3-binucleophiles are found to react at the same rate. This methodology could be extended with their 3-formyl and 3-ester derivatives for the synthesis of pyrimido annulated quinolines.

Synthesis of 2-aryl-1,2,3,4-tetrahydropyridothienoquinolin-4-ones

The synthesis of a new tetracyclic condensed quinoline system is reported by a novel method.The method involves β-enamino carbonyl compound as starting material to get 1-quinolin-2-yl>-3-aryl-2-propen-1-one, which in turn is cyclised