66657-42-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Oxo-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride is used as a reactant for the synthesis of pan-histone deacetylase (pan-HDAC) inhibitors. These inhibitors are important in the development of drugs targeting various diseases, including cancer, neurodegenerative disorders, and inflammatory conditions, by modulating the acetylation state of histone proteins and affecting gene expression.

InChI:InChI=1/C9H8ClNO3S/c10-15(13,14)7-2-3-8-6(5-7)1-4-9(12)11-8/h2-3,5H,1,4H2,(H,11,12)

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 7790-94-5 chlorosulfonic acid 
• 553-03-7 3,4-Dihydrocarbostyril 

Downstream Products

• 1393727-00-8 6-(4-(4-acetylphenyl)piperazin-1-ylsulfonyl)-3,4-dihydroquinolin-2(1H)-one 
• 1616590-44-3 C₁₇H₂₄N₂O₅S 
• 899717-26-1 N-(3,4-dimethylphenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 879178-88-8 N-(4-fluorophenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 912797-10-5 2-oxo-N-o-tolyl-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 1030222-01-5 N-(3,4-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 1345822-54-9 N-(4-chloro-3-methylphenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 912788-04-6 2-oxo-N-m-tolyl-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 912796-94-2 N-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 687593-47-1 N-(4-methoxyphenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 1325810-53-4 N-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 878949-29-2 2-oxo-N-p-tolyl-1,2,3,4-tetrahydroquinoline-6-sulfonamide 
• 909089-35-6 N-(3-fluorophenyl)-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonamide 

Relevant academic research and scientific papers

Discovery of Novel 3,4-Dihydro-2(1H)-Quinolinone Sulfonamide Derivatives as New Tubulin Polymerization Inhibitors with Anti-Cancer Activity

In this paper, a small series of novel quinoline sulfonamide derivatives was synthesized, and their structure of the target compounds were confirmed by 1H NMR and MS. The screening of the news target compounds’ in vitro cytotoxic activities against tumor cell lines by the MTT method was performed. Among them, compound D13 (N-(4-methoxybenzyl)-2-oxo-N-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-sulfonamide exhibited the strongest inhibitory effect on the proliferation of HeLa (IC50: 1.34 μM), and this value correlated well with the inhibitory activities of the compound against tubulin polymerization (IC50: 6.74 μM). In summary, a new type of quinoline-sulfonamide derivative with tubulin polymerization inhibitory activity was discovered, and it can be used as a lead compound for further modification.

Phenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy

Tryptophan metabolism has been recognized as an important mechanism in immune tolerance. Indoleamine 2,3-dioxygenase plays a key role in local tryptophan metabolism via the kynurenine pathway and has emerged as a therapeutic target for cancer immunotherapy. Our prior study identified phenyl benzenesulfonyl hydrazide 2 as a potent in vitro (though not in vivo) inhibitor of indoleamine 2,3-dioxygenase. Further lead optimization to improve in vitro potencies and pharmacokinetic profiles resulted in N′-(4-bromophenyl)-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl hydrazide 40, which demonstrated 59% oral bioavailability and 73% of tumor growth delay without apparent body weight loss in the murine CT26 syngeneic model, after oral administration of 400 mg/kg. Accordingly, 40, is proposed as a potential drug lead worthy of advanced preclinical evaluation.

Design and synthesis of novel and highly-active pan-histone deacetylase (pan-HDAC) inhibitors

Histone deacetylase (HDAC) inhibitions are known to elicit anticancer effects. We designed and synthesized several HDAC inhibitors. Among these compounds, compound 40 exhibited a more than 10-fold stronger inhibitory activity compared with that of suberoylanilide hydroxamic acid (SAHA) against each human HDAC isozyme in vitro (IC50 values of 40: HDAC1, 0.0038 μM; HDAC2, 0.0082 μM; HDAC3, 0.015 μM; HDAC8, 0.0060 μM; HDAC4, 0.058 μM; HDAC9, 0.0052 μM; HDAC6, 0.058 μM). The dose of the administered HDAC inhibitors that contain hydroxamic acid as the zinc-binding group may be reduced by 40. Because the carbostyril subunit is a time-tested structural component of drugs and biologically active compounds, 40 most likely exhibits good absorption, distribution, metabolism, excretion, and toxicity (ADMET). Thus, compound 40 is expected to be a promising therapeutic agent or chemical tool for the investigation of life process.

ETHER DERIVATIVES HAVING 5-LIPOXYGENASE INHIBITORY ACTIVITY

The invention concerns ether derivatives of the formula I Q1?X?Ar?Q2 wherein Q1 is an optionally substituted 9-, 10- or 11-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur; X is oxy, thio, sulphinyl or sulphonyl; Ar is optionally substituted phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazoiediyl, thiadiazoiediyl or oxadiazolediyl; and Q2 is selected from the groups of the formulae II and III: wherein R1 is hydrogen, (2-5C)alkanoyl or optionally substituted benzoyl; R2 is (l-4C)alkyl; and R3 is hydrogen or (l-4C)alkyl; or R2 and R3 are linked to form a methylene, vinylene, ethylene or trimethylene group; or a pharmaceutically-acceptable salt thereof; processes for their preparation; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.

Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. I. Alkyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrates and related compounds

Many alkyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrates and related compounds were synthesized and tested for inhibitory activity against blood platelet aggregation in vitro. Among them, ethyl 4-(2-oxo,1,2,3,4-tetrahydro-6-quinolyloxy)butyrate was