483287-37-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-methylquinoline-3-carbonitrile is used as a synthetic intermediate for the production of various pharmaceuticals. It plays a crucial role in the synthesis of biologically active molecules, contributing to the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical industry, 2-chloro-6-methylquinoline-3-carbonitrile is used as a synthetic intermediate for the production of agrochemicals. Its involvement in the synthesis of various chemical compounds makes it valuable for the development of new agrochemical products.
Used in Fine Chemicals Production:
2-Chloro-6-methylquinoline-3-carbonitrile is also used as a synthetic intermediate in the production of other fine chemicals. Its versatility in synthesis allows for the creation of a wide range of chemical compounds for various applications.

InChI:InChI=1/C11H7ClN2/c1-7-2-3-10-8(4-7)5-9(6-13)11(12)14-10/h2-5H,1H3

Upstream product

• 73568-27-1 2-chloro-6-methylquinoline-3-carbaldehyde 
• 103-89-9 4-Methylacetanilide 
• 106-49-0 p-toluidine 

Downstream Products

• 1415354-58-3 1-benzyl-7-methyl-1H-pyrimido[4,5-b]quinolin-4-one 
• 333329-31-0 2-(benzylamino)-6-methylquinoline-3-carbonitrile 
• 1100051-05-5 6-methyl-2-phenylethynyl-quinoline-3-carbonitrile 

Relevant academic research and scientific papers

Synthesis and biological screening of novel 2-morpholinoquinoline nucleus clubbed with 1,2,4-oxadiazole motifs

Novel series of 2-morpholinoquinoline scaffolds (6a-n), containing the 1,2,4-oxadiazole and moiety, was designed and synthesized in good yield (76–86%). The synthesized compounds were screened for their preliminary in vitro antimicrobial activity against

Synthesis, antimicrobial evaluation, DNA gyrase inhibition, and in silico pharmacokinetic studies of novel quinoline derivatives

Herein, we report the synthesis and in vitro antimicrobial evaluation of novel quinoline derivatives as DNA gyrase inhibitors. The preliminary antimicrobial activity was assessed against a panel of pathogenic microbes including Gram-positive bacteria (Streptococcus pneumoniae and Bacillus subtilis), Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), and fungal strains (Aspergillus fumigatus, Syncephalastrum racemosum, Geotrichum candidum, and Candida albicans). Compounds that revealed the best activity were subjected to further biological studies to determine their minimum inhibitory concentrations (MICs) against the selected pathogens as well as their in vitro activity against the E. coli DNA gyrase, to realize whether their antimicrobial action is mediated via inhibition of this enzyme. Four of the new derivatives (14, 17, 20, and 23) demonstrated a relatively potent antimicrobial activity with MIC values in the range of 0.66–5.29 μg/ml. Among them, compound 14 exhibited a particularly potent broad-spectrum antimicrobial activity against most of the tested strains of bacteria and fungi, with MIC values in the range of 0.66–3.98 μg/ml. A subsequent in vitro investigation against the bacterial DNA gyrase target enzyme revealed a significant potent inhibitory activity of quinoline derivative 14, which can be observed from its IC50 value (3.39 μM). Also, a molecular docking study of the most active compounds was carried out to explore the binding affinity of the new ligands toward the active site of DNA gyrase enzyme as a proposed target of their activity. Furthermore, the ADMET profiles of the most highly effective derivatives were analyzed to evaluate their potentials to be developed as good drug candidates.

The antimicrobial potential and pharmacokinetic profiles of novel quinoline-based scaffolds: synthesis andin silicomechanistic studies as dual DNA gyrase and DHFR inhibitors

The resistance of pathogenic microbes to currently available antimicrobial agents has been considered a global alarming concern. Hence, close attention should be paid to the development of novel potent antimicrobials. Herein, we report the synthesis,in vitroantimicrobial evaluation, of two novel sets of quinoline derivatives as potential DNA gyrase and DHFR inhibitors. The design of new compounds depended on modifying the structural aspects of previously reported fluoroquinolones. In both sets, the methyl group replaced the fluorine atom at C-6. In the first set, the diverse heterocyclic fragments of reported antimicrobial potentials, including pyrazole, isoxazole, and pyrimidine, were attached to C-3 of the quinoline scaffold. In the second set, the quinolone ring was replaced with the pyrazolo[3,4-b]quinoline scaffold to examine the effect of this action on the antimicrobial activity and thein silicovirtual binding with DNA gyrase and DHFR. The preliminary antimicrobial activity of new compounds was assessed against a panel of pathogenic microbes including Gram-positive bacteria (Streptococcus pneumoniaandBacillus subtilis), Gram-negative bacteria (Pseudomonas aeruginosaandEscherichia coli), and fungal strains (Aspergillus fumigatus,Syncephalastrum racemosum, andGeotriucum candidum). Six derivatives displayed relatively potent antimicrobial activity with a percent activity range of 80-113% relative to ampicillin, gentamicin, and amphotericin B as reference antimicrobial agents. Molecular docking studies were conducted to predict the binding affinities of new compounds toward the active sites of DNA gyrase and DHFR as proposed therapeutic targets.

Discovery and optimization of thienopyridine derivatives as novel urea transporter inhibitors

Urea transporters (UTs) play an important role in the urine concentrating mechanism and are recognized as novel targets for developing small molecule inhibitors with salt-sparing diuretic activity. Thienoquinoline derivatives, a class of novel UT-B inhibitors identified by our group, play a significant diuresis in animal model. However, the poor solubility and low bioavailability limited its further development. To overcome these shortcomings, the structure modification of thienoquinoline was carried out in this study, which led to the discovery of novel thienopyridine derivatives as specific urea transporter inhibitors. Further optimization obtained the promising preclinical candidate 8n with not only excellent inhibition effect on urea transporters and diuretic activity on rat model, but also suitable water solubility and Log P value.

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.

An alternate route to the synthesis of imidazo[1,2-a]quinolines using I2-NaI reagent

A new and a facile route to the synthesis of imidazo[1,2-a]quinolines has been described via iodocyclization reaction of 2-allylaminoquinoline derivatives using I2-NaI reagent.

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.

A one pot method of conversion of aldehydes into nitriles using iodine in ammonia water: Synthesis of 2-chloro-3-cyanoquinolines

One pot rapid transformations of heteroaromatic carbaldehyde to cyano group using cheap and easily available iodine in aqueous ammonia has been described.

Pyrazolo-fused quinoline analogues: Synthesis of 1H-pyrazolo [3, 4-b] quinolines and 3-amino-1H-pyrazolo [3, 4-b] quinolines from 3-formyl and 3-cyano-2-chloroquinolines

Stepwise synthesis of 1H-pyrazolo [3, 4-b] quinolines 6 has been described from the reactions of 2-chloro-3-formylquinolines 1 with ethyleneglycol and hydrazine hydrate reagents in sequence followed by hydrolysis with BiCl 3. However, 3-amino-1H-pyrazolo[3, 4-b]quinolines 7 have been synthesized from 2-chloro-3-cyanoquinolines 2 with excess of hydrazine hydrate in one step. The functional group manipulation of amino group in compounds 7 has also been studied.

Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities

A simple and regioselective synthesis of 2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides bearing electron donating groups at m-position. However, yields of quinolines having electron donating groups are good in all cases. Further, the nucleophilic substitution reaction of the quinolines is also investigated. Similarly, the formyl group in the quinolines is subjected to further transformation into cyano (CAN-NH3) and alkoxycarbonyl (NIS-K2CO3/alcohols) groups to afford corresponding 3-cyano and 3-alkoxycarbonylquinolines, respectively.