101617-91-8

Usage

Uses

Used in Pharmaceutical Research:
2-Chloro-6-methoxyquinoline-3-carbonitrile is used as a key intermediate in the synthesis of various bioactive molecules, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemicals:
2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE may also find applications in the field of agrochemicals, where it could be utilized in the development of new pesticides or other agricultural chemicals to improve crop protection and yield.
Used in Materials Science:
2-Chloro-6-methoxyquinoline-3-carbonitrile has potential uses in materials science, where it could be incorporated into the design of advanced materials with specific properties, such as improved conductivity or enhanced stability.

InChI:InChI=1/C11H7ClN2O/c1-15-9-2-3-10-7(5-9)4-8(6-13)11(12)14-10/h2-5H,1H3

Upstream product

• 73568-29-3 2-chloro-6-methoxyquinolin-3-carboxaldehyde 
• 51-66-1 4-methoxyacetanilide 

Downstream Products

• 95733-92-9 (2-Chloro-6-methoxy-quinolin-3-yl)-phenyl-methanone 
• 123990-79-4 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile 
• 1415354-59-4 1-benzyl-7-methoxy-1H-pyrimido[4,5-b]quinolin-4-one 
• 1415354-69-6 2-(benzylamino)-6-methoxyquinoline-3-carbonitrile 
• 1371588-07-6 4-(3-cyano-6-hydroxyquinolin-2-yl)benzoic acid 
• 1371588-96-3 4-(3-cyano-6-methoxyquinolin-2-yl)benzoic acid 

Relevant academic research and scientific papers

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.

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.

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.

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.

A clean conversion of aldehydes to nitriles using a solid-supported hydrazine

A polymer-supported hydrazine reagent has been applied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for combinatorial chemistry programmes.

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

Pyrazolo[3,4-b]quinolines and their use as antiviral agents

Pyrazolo[3,4-b]quinolines having the formula STR1 where R is hydrogen, hydroxy or alkoxy; R2 is halogen, cyano, carbamyl, carboxy, lower-alkylcarbonyl, amino or aminomethyl; and R1 is hydrogen or selected substituents as defined herein, are useful as antiviral agents and/or as vasodilators.