1677-42-5

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
CHEMBRDG-BB 6631006 is used as a research compound for exploring its potential in the development of new pharmaceuticals. Its unique structure and properties make it a candidate for further investigation into its therapeutic capabilities.
Used in Antihypertensive Applications:
In the field of cardiovascular health, CHEMBRDG-BB 6631006 is used as an antihypertensive agent for its ability to inhibit the angiotensin-converting enzyme (ACE). This inhibition can help regulate blood pressure and is a key mechanism in the treatment of hypertension.
Used in Anti-inflammatory Applications:
CHEMBRDG-BB 6631006 is also being studied for its potential as an anti-inflammatory agent. Its properties may contribute to reducing inflammation, which is important in the treatment of various conditions affected by inflammatory processes.
Used in Antioxidant Applications:
CHEMBRDG-BB 6631006 is being investigated for its potential antioxidant properties, which could be beneficial in protecting cells from oxidative damage, a common factor in many diseases and aging processes.
Further research is required to fully understand and harness the potential therapeutic applications of CHEMBRDG-BB 6631006, particularly in the areas of hypertension, inflammation, and oxidative stress.

InChI:InChI=1/C10H9NO2/c1-6-3-2-4-7-8(12)5-9(13)11-10(6)7/h2-5H,1H3,(H2,11,12,13)

Upstream product

• 95-53-4 o-toluidine 
• 78987-20-9 3-<(2-methylphenyl)amino>-3-oxopropanoic acid 
• 105-53-3 diethyl malonate 
• 10378-79-7 N₁,N₃-di-o-tolylmalonamide 

Downstream Products

• 102878-20-6 2,4-dichloro-8-methylquinoline 
• 1450665-40-3 3-[2-(3-chlorophenyl)hydrazono]-8-methylquinoline-2,4-(1H,3H)-dione 
• 1450665-48-1 8-methyl-3-[2-(m-tolyl)hydrazono]quinoline-2,4-(1H,3H)-dione 
• 1436460-87-5 C₁₆H₁₂N₄O₄ 
• 1436460-86-4 C₁₈H₁₅N₃O₃ 
• 1436460-85-3 C₁₆H₁₂FN₃O₂ 
• 1436460-84-2 C₁₆H₁₂ClN₃O₂ 
• 1436460-83-1 C₁₆H₁₂BrN₃O₂ 
• 1436460-82-0 C₁₆H₁₂IN₃O₂ 
• 1436460-81-9 C₁₇H₁₅N₃O₂ 
• 1436460-80-8 C₁₇H₁₅N₃O₃ 
• 360078-59-7 8-methyl-4-(triphenylphosphoranylideneamino)quinoline-2(1H)-thione 
• 360078-50-8 8-methyl-4-(triphenylphosphoranylideneamino)quinolin-2(1H)-one 
• 113226-20-3 4-chloro-8-methylquinoline-2(1H)-one 

Relevant academic research and scientific papers

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones

Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.

Natural Product-Mimetic Scaffolds with Privileged Heterocyclic Systems: Design, Synthesis, and Evaluation of Antioxidant Activity of Quinazoquinobenzothiazinones

(Chemical Equation Presented) Structurally diverse quinazolinoquinolinobenzothiazinones based on rutaecarpine structural framework with hybrid structural features of three medicinally privileged heterocyclic systems has been synthesized as natural product-mimetic scaffolds involving the use of multi-step reaction sequences. The synthesized quinazolinoquinolinobenzothiazinones have been evaluated for their antioxidant and radical scavenging activities.

Synthesis and SAR studies of novel 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives for anticancer activity

Background and Purpose 4-Phenylquinolin-2(1H)-one (4-PQ) derivatives can induce cancer cell apoptosis. Additional new 4-PQ analogs were investigated as more effective, less toxic antitumour agents. Experimental Approach Forty-five 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives were synthesized. Antiproliferative activities were evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliun bromide assay and structure-activity relationship correlations were established. Compounds 9b, 9c, 9e and 11e were also evaluated against the National Cancer Institute-60 human cancer cell line panel. Hoechst 33258 and Annexin V-FITC/PI staining assays were used to detect apoptosis, while inhibition of microtubule polymerization was assayed by fluorescence microscopy. Effects on the cell cycle were assessed by flow cytometry and on apoptosis-related proteins (active caspase-3, -8 and -9, procaspase-3, -8, -9, PARP, Bid, Bcl-xL and Bcl-2) by Western blotting. Key Results Nine 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives (7e, 8e, 9b, 9c, 9e, 10c, 10e, 11c and 11e) displayed high potency against HL-60, Hep3B, H460, and COLO 205 cancer cells (IC50 50 > 50 μM). Particularly, compound 11e exhibited nanomolar potency against COLO 205 cancer cells. Mechanistic studies indicated that compound 11e disrupted microtubule assembly and induced G2/M arrest, polyploidy and apoptosis via the intrinsic and extrinsic signalling pathways. Activation of JNK could play a role in TRAIL-induced COLO 205 apoptosis. Conclusion and Implications New quinolone derivatives were identified as potential pro-apoptotic agents. Compound 11e could be a promising lead compound for future antitumour agent development.

Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone: Synthesis, UV-vis studies and biological activity

In this study, N,N′-di-(2-methylphenyl)malonamide was synthesized and reacted with polyphosphoric acid to afford 8-methyl-4-hydroxyl-2-quinolone. Eight novel azo disperse dyes were then synthesized by linking diazotized p-substituted aniline derivatives w

Synthesis and antioxidant activity of quinolinobenzothiazinones

A new series of structurally diverse quinolinobenzothiazinones has been synthesized with the annulation of heterocyclic structural pharmacophores. The synthesized quinolinobenzothiazinones have been evaluated for their antioxidant (LPO & GSH) and radical scavenging activities (DPPH and ABTS assays).

Clean and convenient one-pot synthesis of 4-hydroxycoumarin and 4-hydroxy-2-quinolinone derivatives

A simple, efficient, and environmentally friendly procedure has been developed for the reaction of Meldrum's acid with phenol, substituted phenols, aniline, or substituted anilines with Eaton's reagent (phosphoric anhydride+methylsulfonic acid) as cyclization reagent. 4-Hydroxycoumarins and 4-hydroxy-2-quinolinones were synthesized in moderate yields by carrying out the reaction in solvent-free, convenient, and clean one-pot preparation.

Quinone methide reactions: Synthesis of novel pyranodiquinolines

The reaction of alkaline 4-hydroxyquinolin-2(1H)-ones (1) with vinyl acetate has been studied.Interestingly, 1,1-diquonolinoethane formed via a quinoline-quinone methide intermediate undergoes dehydration in situ by two paths yielding the isomeric 7-methylpyranodiquinolines (3 and 4).