145369-94-4

Usage

Chemical Properties

Tan powder

InChI:InChI=1/C10H7Cl2N/c1-6-8(11)3-2-7-9(12)4-5-13-10(6)7/h2-5H,1H3

Upstream product

• 98948-95-9 6-bromo-4-hydroxyquinoline-3-carboxylic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 106-40-1 4-bromo-aniline 
• 122794-99-4 6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester 
• 76228-06-3 6-bromo-2,3-dihydro-4(1H)-quinolinone 
• 141-82-2 malonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 15568-85-1 5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 101937-44-4 diethyl 2-((4-bromophenylamino)methylene)malonate 
• 149-73-5 trimethyl orthoformate 
• 98948-95-9 6-bromo-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 79607-23-1 ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 1320361-74-7 ethyl 3-(4-bromoanilino)propenoate 

Downstream Products

• 65340-70-7 6-bromo-4-chloroquinoline 
• 857762-32-4 6-bromo-3-chloroquinolin-4-ol 
• 857758-88-4 3,6-dibromo-quinolin-4-ol 
• 927801-17-0 6-bromo-3,4-dichloroquinoline 
• 927801-19-2 3,6-dibromo-4-chloro-quinoline 
• 1375077-25-0 4-(4-(6-bromoquinolin-4-yloxy)-6-chloro-1,3,5-triazin-2-ylamino)-benzonitrile 
• 1551455-21-0 N-(2-methoxy-5-(4-((trimethylsilyl)ethynyl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1551455-28-7 2-fluoro-N-(2-methoxy-5-(4-((trimethylsilyl)ethynyl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 927801-23-8 6-bromo-4-iodoquinoline 
• 1086062-75-0 6-bromo-4-chloroquinoline hydrochloride 
• 1551453-19-0 2,4-difluoro-N-(5-(4-(3-hydroxyprop-1-yn-1-yl)quinolin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1551454-59-1 2,4-difluoro-N-(2-methoxy-5-(4-((trimethylsilyl)ethynyl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1551453-47-4 N-(5-(4-ethynylquinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1551453-50-9 N-(5-(4-((1H-pyrazol-4-yl)ethynyl)quinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 

Relevant academic research and scientific papers

A Selective and Orally Bioavailable Quinoline-6-Carbonitrile-Based Inhibitor of CDK8/19 Mediator Kinase with Tumor-Enriched Pharmacokinetics

Senexins are potent and selective quinazoline inhibitors of CDK8/19 Mediator kinases. To improve their potency and metabolic stability, quinoline-based derivatives were designed through a structure-guided strategy based on the simulated drug–target dockin

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

QUINOLINE-BASED COMPOUNDS AND METHODS OF INHIBITING CDK8/19

Disclosed herein are quinoline-based compounds and method for inhibiting CDK8 or CDK19 for the intervention in diseases, disorders, and conditions. The quinoline-based composition comprise substituents at quinoline ring positions 4 and 6, wherein the substituent at position 4 is selected from a substituted or unsubstituted arylalkylamine or a substituted or unsubstituted arylhetrocyclylamine. Pharmaceutical compositions comprising the substituted qunioline compositions, methods of inhibiting CDK8 or CDK19, and methods of treating CDK8/19-associated diseases, disorders, or conditions are also disclosed.

BICYCLE TOPOISOMERASE I INHIBITING COMPOUNDS, PROCESS FOR PREPARATION AND USE THEREOF

The invention described herein relates to the compounds of Formula I for treating diseases and disorders for which inhibition or modulation of the topoisomerase I enzyme produces a physiologically beneficial response, in particular for the treatment of breast cancer. Also provided is the process of preparing compounds of Formula I.

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

Design, synthesis, and antitumor evaluation of quinoline-imidazole derivatives

A series of compounds bearing quinoline-imidazole (8a–e, 9a–e, 10a–e, 11a–e, and 12a–e) not reported previously were designed and synthesized. The target compounds were evaluated for antitumor activity against A549, PC-3, HepG2, and MCF-7 cells by the MTT method, with NVP-BEZ235 being the positive control. Most compounds showed moderate activity and compound 12a showed the best activity against HepG2, A549, and PC-3 cells, with half-maximal inhibitory concentration (IC50) values of 2.42 ± 1.02 μM, 6.29 ± 0.99 μM, and 5.11 ± 1.00 μM, respectively, which was equal to NVP-BEZ235 (0.54 ± 0.13 μM, 0.36 ± 0.06 μM, 0.20 ± 0.01 μM). Besides, the IC50 value of 12a against the cell line WI-38 (human fetal lung fibroblasts) was 32.8 ± 1.23 μM, indicating that the target compounds were selective for cancer cells. So, 11a and 12a were evaluated against PI3Kα and mTOR to find out if the compounds acted through the PI3K-Akt-mTOR signal transduction pathway. The inhibition ratios to PI3Kα and mTOR were slightly lower than that of NVP-BEZ235, suggesting there may be some other mechanisms of action. The structure–activity relationships and docking study of 11a and 12a revealed that the latter was superior. Moreover, the target compounds showed better in vitro anticancer activity when the C-6 of the quinoline ring was replaced by a bromine atom.

Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors

Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.

Sulfonylurea compound as well as preparation method and application thereof

The invention discloses a sulfonylurea compound, geometrical isomers or pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and a preparation method thereof. The sulfonylurea compound, the pharmaceutically acceptable salts, hydrates or solvates serving as active ingredients are mixed with pharmaceutically acceptable carriers or excipients to prepare compositions and preparedinto clinically acceptable dosage forms. The invention further discloses application of the compounds in preparation of medicines for treating and/or preventing proliferative diseases, application inpreparation of medicines for treating and/or preventing cancers, and application in preparation of medicines for treating and/or prostatic cancer, lung cancer and breast cancer.

Oxidation method of 4-oxo-2,3-dihydroquinoline compound

The invention discloses an oxidation method of a 4-oxo-2,3-dihydroquinoline compound. The method comprises the following steps: taking the 4-oxo-2,3-dihydroquinoline compound as a raw material; addingan organic solvent, an acidifying agent and an oxidizing agent; performing oxidation reaction at 50-85 DEG C; and after the reaction is finished, performing post-treatment on the reaction liquid to obtain a 4-hydroxyquinoline compound. Various raw materials used by the preparation method disclosed by the invention are simple and easy to obtain, are industrial products and have wide sources and low price; the preparation method is simple, easy to operate and high in product yield; compared with the traditional oxidation method of the 4-oxo-2,3-dihydroquinoline compound, the method disclosed bythe invention has the advantages of being more efficient and simpler in post-treatment; and the method is especially important for the industrialization of the product.

6-bromo-4-chloroquinoline preparation method

The invention discloses a 6-bromo-4-chloroquinoline preparation method. 4-bromaniline, ethyl propiolate, phosphorus trichloride and the like are used as raw materials to obtain a target product 6-bromo-4-chloroquinoline through three-step reaction. The 6-bromo-4-chloroquinoline preparation method is convenient and simple in operation and environment friendly, the comprehensive yield is 70% or above and remarkably increased as compared with existing yield which is 26-42%, existing medicine production cost is sharply reduced, and the 6-bromo-4-chloroquinoline preparation method is suitable for industrial mass production.