68236-23-7

Basic information

• Product Name: 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE
• Synonyms: 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE;2-CHLORO-6,7-DIMETHOXY-3-QUINOLINECARBALDEHYDE;OTAVA-BB 1045294;AG-690/15443853;BAS 01520557;Oprea1_197761;Oprea1_832501;ST5253554
• CAS NO: 68236-23-7
• Molecular Formula: C₁₂H₁₀ClNO₃
• Molecular Weight: 251.67
• Mol File: 68236-23-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 265-267 °C
• Boiling Point: 393.9°C at 760 mmHg
• Flash Point: 192°C
• Appearance: /
• Density: 1.335g/cm³
• Vapor Pressure: 2.06E-06mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.95±0.50(Predicted)
• CAS DataBase Reference: 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE(68236-23-7)
• EPA Substance Registry System: 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE(68236-23-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 68236-23-7(Hazardous Substances Data)

Usage

General Description

2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE is a chemical compound with the molecular formula C12H10ClNO3. It is a quinoline derivative with a chlorine atom and two methoxy groups attached to the quinoline ring, as well as an aldehyde group at position 3. 2-CHLORO-6,7-DIMETHOXY-QUINOLINE-3-CARBALDEHYDE is commonly used in organic synthesis and medicinal chemistry, where it can serve as a building block for the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and chemical properties make it valuable for creating new drugs and studying the biological activities of related molecules. Additionally, this compound has potential applications in pesticide and herbicide development due to its structural features.

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

• 101382-56-3 6,7-Dimethoxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehyde 
• 112181-70-1 (E)-3-(2-Chloro-6,7-dimethoxy-quinolin-3-yl)-2-(4-chloro-phenylsulfanyl)-acrylonitrile 
• 112181-69-8 (Z)-3-(2-Chloro-6,7-dimethoxy-quinolin-3-yl)-2-(4-chloro-phenyl)-acrylonitrile 
• 92172-68-4 (2-Chloro-6,7-dimethoxy-8-nitro-quinolin-3-ylmethyl)-(4-methoxy-phenyl)-amine 
• 92172-73-1 2-Chloro-6,7-dimethoxy-8-nitro-3-(3-trifluoromethyl-phenoxymethyl)-quinoline 
• 92172-76-4 2-Chloro-6,7-dimethoxy-3-[(4-methoxy-phenylamino)-methyl]-quinolin-8-ylamine; compound with phosphoric acid 
• 94741-56-7 6,7-Dimethoxy-3-phenyl-thieno[2,3-b]quinoline-2-carboxylic acid methyl ester 
• 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 
• 94741-42-1 3-Acetyl-2-chloro-6,7-dimethoxyquinoline 
• 94741-44-3 (2-Chloro-6,7-dimethoxy-quinolin-3-yl)-phenyl-methanone 
• 93299-56-0 2-chloro-6,7-dimethoxy-3-quinolinecarbonitrile 
• 106835-45-4 3-Amino-6,7-dimethoxy-1H-pyrazolo<3,4-b>quinoline 

Relevant articles and documents

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.

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.

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.