Production Method 1

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Toluene ;  rt → reflux; 6 h, reflux

Reference

Process for preparation of main ring of quinolone

, China, , ,

Production Method 2

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Toluene ;  rt → reflux; 8 h, reflux

Reference

Process for the preparation of dihydroquinolone carboxylates

, China, , ,

Production Method 3

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Sodium fluoride Solvents: N-Methyl-2-pyrrolidone

Reference

Preparation of 3-amino-2-(het)aroylacrylic acid derivatives

, Germany, , ,

Production Method 4

94695-50-8

765-30-0

94242-51-0

Reaction Conditions

1.1 Solvents: Acetic anhydride ;  2 h, 150 °C; 150 °C → 80 °C
1.2 Solvents: tert-Butanol ;  80 °C → 10 °C; 10 °C; 0.5 h, 10 °C; 10 °C → 45 °C; overnight, 45 °C
1.3 Reagents: Potassium tert-butoxide Solvents: tert-Butanol ;  overnight, 50 °C

Reference

Process for preparation of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid

, China, , ,

Production Method 5

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol ;  5 h, 90 °C

Reference

Quinolone carboxylic acid compound and intermediate, preparation method and application thereof in preparation of anti-gram-positive bacteria or anti-gram-negative bacteria drugs

, China, , ,

Production Method 6

94695-50-8

765-30-0

94242-51-0

Reaction Conditions

1.1 Catalysts: Acetic anhydride
1.2 Solvents: Dimethyl sulfoxide

Reference

Diethyl Malonate

Romeder, Gerard, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 7

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol

Reference

1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure activity relationships at N1 for the quinolone antibacterials

Domagala, John M.; Heifetz, Carl L.; Hutt, Marland P.; Mich, Thomas F.; Nichols, Jeffry B.; et al, Journal of Medicinal Chemistry, 1988, 31(5), 991-1001

Production Method 8

104599-80-6

104600-32-0

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide

Reference

Cycloaracylation of enamines. I. Synthesis of 4-quinolone-3-carboxylic acids

Grohe, Klaus; Heitzer, Helmut, Liebigs Annalen der Chemie, 1987, (1), 29-37

Production Method 9

94695-51-9

94242-51-0

Reaction Conditions

Reference

Antibacterial 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic acids

, Federal Republic of Germany, , ,

Production Method 10

94695-51-9

94242-51-0

Reaction Conditions

Reference

7-(3-Aryl-1-piperazinyl)- and 7-(3-cyclohexyl-1-piperazinyl)quinolone-3-carboxylic acids

, Federal Republic of Germany, , ,

Production Method 11

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Sodium fluoride Solvents: Dimethylformamide ;  2 h, reflux

Reference

Preparation of uracils and related compounds as antibacterials that inhibit bacterial DNA polymerase IIIC and type II bacterial topoisomerase.

, United States, , ,

Production Method 12

94695-48-4

765-30-0

924-99-2

94242-51-0

Reaction Conditions

1.1 Reagents: Tributylamine Solvents: Toluene ;  40 °C; 1 h, 40 °C
1.2 rt
1.3 Reagents: Carbon dioxide ;  1 h, 2 atm, rt
1.4 Reagents: Potassium carbonate Solvents: Toluene ;  110 - 115 °C; 110 - 115 °C

Reference

Process for preparation of quinolone main ring compounds

, China, , ,

Production Method 13

4637-24-5

94695-50-8

765-30-0

94242-51-0

Reaction Conditions

Reference

Preparation of pyridinylquinolones as antibacterials

, European Patent Organization, , ,

Production Method 14

6148-64-7

94695-48-4

765-30-0

94242-51-0

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Magnesium chloride ;  10 - 25 °C
1.2 Reagents: Hydrochloric acid
1.3 Reagents: Acetic anhydride
1.4 Solvents: Dimethyl sulfoxide

Reference

Diethyl malonate

Romeder, Gerard, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-4

Production Method 15

94695-51-9

94242-51-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  80 °C

Reference

2-aryl-3-carbonylquinolones: design, synthesis and biological evaluation of novel HCV NS5B polymerase inhibitors

Wang, Shenfeng; Lin, Jianping; He, Peilan; Zuo, Jianping; Long, Yaqiu, Huaxue Xuebao, 2014, 72(8), 906-913

Production Method 16

104600-32-0

94242-51-0

Reaction Conditions

Reference

Product subclass 3: enol ethers

Milata, V.; Radl, S.; Voltrova, S., Science of Synthesis, 2008, 32, 589-756

Production Method 17

104600-32-0

94242-51-0

Reaction Conditions

1.1 Reagents: Sodium hydride

Reference

Potent non-6-fluoro-substituted quinolone antibacterials: synthesis and biological activity

Ledoussal, Benoit; Bouzard, Daniel; Coroneos, Evangelos, Journal of Medicinal Chemistry, 1992, 35(1), 198-200

Production Method 18

94695-51-9

94242-51-0

Reaction Conditions

Reference

Substituted naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents

, European Patent Organization, , ,

Production Method 19

94242-50-9

94242-51-0

Reaction Conditions

Reference

Quinolinonecarboxylic acid derivatives

, Japan, , ,

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester Raw materials

• Ethyl potassium malonate
• (dimethoxymethyl)dimethylamine
• Benzenepropanoic acid, α-[(cyclopropylamino)methylene]-2,3,4,5-tetrafluoro-β-oxo-, ethyl ester, (E)- (9CI)
• (Z)-ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylate
• Benzenepropanoic acid, α-[(cyclopropylamino)methylene]-2,3,4,5-tetrafluoro-β-oxo-, ethyl ester
• 2,3,4,5-Tetrafluorobenzoyl chloride
• 2,3,4,5-Tetrafluorobenzoylacetic Acid Ethyl Ester
• Propanedioic acid, 2-[[cyclopropyl(2,3,4-trifluorophenyl)amino]methylene]-, 1,3-diethyl ester
• cyclopropanamine
• Ethyl 3-(N,N-dimethylamino)acrylate

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester Preparation Products

• 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester (94242-51-0)

• 1. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 2. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 3. Acetyl protected thiol methacrylic polymers as effective ligands to keep quantum dots in luminescent standby mode?
  Marta Liras,Isabel Quijada-Garrido,Marta Palacios-Cuesta,Sonia Mu?oz-Durieux,Olga García Polym. Chem., 2014,5, 433-442
• 4. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 5. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392

1-Cyclopropyl-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinecarboxylic Acid Ethyl Ester (CAS No. 94242-51-0)

The compound 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester (CAS No. 94242-51-0) is a highly specialized organic molecule with a complex structure that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound is characterized by its unique quinoline skeleton, which serves as a versatile platform for various functional groups. The presence of a cyclopropyl group and trifluoromethyl substituents at positions 6, 7, and 8 further enhances its chemical reactivity and biological activity.

Recent studies have highlighted the potential of this compound as a building block for drug discovery. The quinoline core is known for its ability to interact with various biological targets, such as kinases and G-protein coupled receptors (GPCRs). The trifluoromethyl groups contribute to the molecule's lipophilicity and stability, making it an ideal candidate for designing drugs with improved pharmacokinetic profiles. Additionally, the cyclopropyl group introduces strain and rigidity into the molecule, which can enhance selectivity towards specific biological targets.

In terms of synthesis, this compound is typically prepared through a multi-step process involving Friedel-Crafts alkylation, trifluorination, and esterification reactions. The use of transition metal catalysts, such as palladium complexes, has been reported to facilitate key steps in its construction. Researchers have also explored alternative routes using microwave-assisted synthesis to improve reaction efficiency and reduce production time.

From a materials science perspective, this compound exhibits interesting electronic properties due to its conjugated π-system. Studies have shown that it can act as a precursor for the synthesis of advanced materials, such as organic semiconductors and light-emitting polymers. Its ability to form self-assembled monolayers (SAMs) has also been investigated for applications in nanotechnology and surface engineering.

One of the most promising applications of this compound lies in its potential as an antimicrobial agent. Preclinical studies have demonstrated that it exhibits potent activity against a range of bacterial and fungal pathogens. The trifluoromethyl groups are believed to play a critical role in disrupting microbial cell membranes, while the quinoline core contributes to its broad-spectrum activity.

Furthermore, this compound has shown potential in the field of cancer therapy. Preclinical models have revealed that it can induce apoptosis in various cancer cell lines by targeting key signaling pathways, such as the MAPK/ERK pathway. Its ability to cross the blood-brain barrier (BBB) makes it particularly attractive for treating brain tumors.

In terms of environmental impact, this compound has been evaluated for its biodegradability and ecotoxicity. Studies indicate that it undergoes rapid degradation under aerobic conditions, minimizing its persistence in the environment. However, further research is needed to assess its long-term effects on aquatic ecosystems.

The development of this compound has also led to advancements in analytical techniques for its characterization. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy have been instrumental in confirming its structure and purity. Researchers have also employed computational methods, such as density functional theory (DFT), to study its electronic properties and reactivity.

In conclusion, 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester (CAS No. 94242-51-0) is a multifaceted compound with significant potential in drug discovery, materials science, and biotechnology. Its unique structure and functional groups make it a valuable tool for addressing complex scientific challenges across various disciplines.

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