68236-23-7

Usage

Uses

Used in Organic Synthesis:
2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE is used as a building block in organic synthesis for the creation of various pharmaceuticals and bioactive compounds. Its unique structure and chemical properties contribute to the synthesis of new drugs and the study of the biological activities of related molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE serves as a key intermediate for the synthesis of potential therapeutic agents. Its structural features allow for the development of compounds with specific biological activities, enhancing the discovery of new drugs.
Used in Pesticide and Herbicide Development:
2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE has potential applications in the development of pesticides and herbicides. Its structural features make it a candidate for creating compounds with pesticidal and herbicidal properties, contributing to the advancement of agricultural chemicals.

InChI:InChI=1/C12H10ClNO3/c1-16-10-4-7-3-8(6-15)12(13)14-9(7)5-11(10)17-2/h3-6H,1-2H3

Upstream product

• 881-70-9 3',4'-dimethoxyacetanilide 
• 68-12-2 N,N-dimethyl-formamide 
• 6315-89-5 3,4-dimethoxyaniline 
• 95460-42-7 2-chloro-6,7-dimethoxy-quinoline-3-aldoxime 

Downstream Products

• 112181-70-1 (E)-3-(2-Chloro-6,7-dimethoxy-quinolin-3-yl)-2-(4-chloro-phenylsulfanyl)-acrylonitrile 
• 95733-86-1 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-(4-methoxy-phenyl)-methanol 
• 95733-95-2 6,7-Dimethoxy-3-phenyl-isoxazolo[5,4-b]quinoline 
• 95734-01-3 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-phenyl-methanone oxime 
• 95733-96-3 6,7-Dimethoxy-3-(4-methoxy-phenyl)-isoxazolo[5,4-b]quinoline 
• 95733-90-7 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-(4-methoxy-phenyl)-methanone 
• 95734-02-4 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-(4-methoxy-phenyl)-methanone oxime 
• 106835-45-4 3-Amino-6,7-dimethoxy-1H-pyrazolo<3,4-b>quinoline 
• 93299-56-0 2-chloro-6,7-dimethoxy-3-quinolinecarbonitrile 
• 5278-37-5 6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 94741-44-3 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-phenyl-methanone 
• 94741-42-1 3-Acetyl-2-chloro-6,7-dimethoxyquinoline 
• 94741-36-3 (2R,3R)-3-Hydroxy-6,7-dimethoxy-3-phenyl-2,3-dihydro-thieno[2,3-b]quinoline-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis, structure-activity relationship and molecular docking studies of novel quinoline-chalcone hybrids as potential anticancer agents and tubulin inhibitors

A new series of quinoline-chalcone hybrids was synthesized. The structures of these compounds were characterized by spectroscopic methods including 1H and 13CNMR and mass spectroscopy. The cytotoxic activity of compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma) and A2780/RCIS (Cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), MCF-7/MX (Mitoxantrone resistant human breast cancer cells) and normal Huvec cells. The structure-activity relationship of synthesized compounds is discussed. Among quinolines 5e, 5g and 5j possessing benzoyl group showed significant cytotoxic activity against both resistant cancer cells and their parents. Compounds 5g and 5j, demonstrated the most antiproliferative activity with IC50 values ranging from 2.32 to 22.4 μM. They were also identified as tubulin inhibitors and induced cell cycle arrest at G2/M phase and apoptosis. Compound 5j induced more arrest at G2/M phase in four cancer cell lines compared to compound 5g. Finally, molecular dynamics simulation and molecular docking studies of compound 5j into the colchicine-binding site of tubulin demonstrated the possible interaction of this compound in the active site of tubulin.

Design of new quinolin-2-one-pyrimidine hybrids as sphingosine kinases inhibitors

Sphingosine-1-phosphate is now emerging as an important player in cancer, inflammation, autoimmune, neurological and cardiovascular disorders. Abundance evidence in animal and humans cancer models has shown that SphK1 is linked to cancer. Thus, there is a

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.

Design, synthesis and evaluation of 3-quinoline carboxylic acids as new inhibitors of protein kinase CK2

In this article, the derivatives of 3-quinoline carboxylic acid were studied as inhibitors of protein kinase CK2. Forty-three new compounds were synthesized. Among them 22 compounds inhibiting CK2 with IC50 in the range from 0.65 to 18.2 μM were identified. The most active inhibitors were found among tetrazolo-quinoline-4-carboxylic acid and 2-aminoquinoline-3-carboxylic acid derivatives.

Synthesis and biological evaluation of new rhodanine analogues bearing 2-chloroquinoline and benzo[h]quinoline scaffolds as anticancer agents

Several rhodanine derivatives (9-39) were synthesized for evaluation of their potential as anticancer agents. Villsmeier cyclization to synthesize aza-aromatic aldehydes, rhodanine derivatives preparation and Knoevenagel type of condensation between the rhodanines and aza-aromatic aldehydes are key steps used for the synthesis of 31 compounds. In vitro antiproliferative activity of the synthesized rhodanine derivatives (9-39) was studied on a panel of six human tumor cell lines viz. HGC, MNK-74, MCF-7, MDAMB-231, DU-145 and PC-3 cell lines. Some of the compounds were capable of inhibiting the proliferation of cancer cell lines at a micromolar concentration. Six compounds are found to be potent against HGC cell lines; compound 15 is found to be active against HGC - Gastric, MCF7 - Breast Cancer and DU145 - Prostate Cancer cell lines; compound 39 is potent against MNK-74; four compounds are found to be potent against MCF-7 cell lines; three compounds are active against MDAMB-231; nine compounds are found to be potent against DU-145; three compounds are active against PC-3 cell lines. These compounds constitute a promising starting point for the development of novel and more potent anticancer agents in future.

Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes

Various quinoline carboxaldehydes were prepared from corresponding anilides using classical Vilsmeier-Haack reaction conditions and transformed into their Baylis-Hillman adducts. The synthesized Baylis-Hillman adducts were screened for their in vitro antimalarial activity against Plasmodium falciparum . Most of the compounds out of 21 compounds synthesized and screened exhibited substantial antimalarial activity. by Walter de Gruyter.

Synthesis and SAR of 2-aryl-3-aminomethylquinolines as agonists of the bile acid receptor TGR5

Optimization of a screening hit from uHTS led to the discovery of TGR5 agonist 32, which was shown to have activity in a rodent model for diabetes.

A convenient access to biquinoline carbaldehydes using nickel-phosphine complex-mediated homocoupling of haloquinoline carbaldehydes in one-pot reaction

The homocoupling of 2-chloro-carbaldehyde derivatives gave the corresponding 2,2'-biquinolines by using the in situ generated reactive reagent Ni[(PPh3)]4. Several new 2-chloro-3-(1.3 dioxalan-2yl) quinoline derivatives are synthesized and structurally characterized. The overall structures of biquinoline derivatives are not planar.

HCV INHIBITORS AND METHODS OF USING THEM

The present invention comprises tetrazoloquinoline-compounds that are inhibitors of HCV. Compositions comprising the compounds in combination with a pharmaceutically acceptable carrier are also disclosed, as are methods of using the compounds and composit

Synthesis of APTRA derivatives as building blocks for low-affinity fluorescent Ca2+ indicators

A new method for the synthesis of trialkyl aminophenoltriacetates (APTRA triesters) and the functionalization of these into suitable building blocks for potential fully conjugated low-affinity fluorescent Ca2+ indicators are described. Georg Th