103772-13-0

Basic information

• Product Name: 1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3- QUINOLINECARBOXYLIC ACID ETHYL ESTER
• Synonyms: 1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3- QUINOLINECARBOXYLIC ACID ETHYL ESTER
• CAS NO: 103772-13-0
• Molecular Formula: C₁₅H₁₃F₃N₂O₃
• Molecular Weight: 326.273
• Mol File: 103772-13-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3- QUINOLINECARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3- QUINOLINECARBOXYLIC ACID ETHYL ESTER(103772-13-0)
• EPA Substance Registry System: 1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3- QUINOLINECARBOXYLIC ACID ETHYL ESTER(103772-13-0)

Safety Data

• Hazardous Substances Data: 103772-13-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclopropyl-5-amido-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester serves as a key intermediate in the synthesis of various pharmaceutical agents. Its unique structure, including the cyclopropyl and trifluoro groups, can potentially enhance the pharmacokinetic and pharmacodynamic properties of the resulting drugs, such as improving their solubility, stability, and bioavailability.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound is utilized as a building block for the design and development of novel therapeutic agents. Its structural attributes, such as the quinoline core and the ethyl ester functionality, offer opportunities for further chemical modifications and optimization to achieve desired biological activities, including potential antimicrobial, anticancer, or other therapeutic effects.
Used in Chemical Synthesis:
1-Cyclopropyl-5-amido-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester is employed as a synthetic precursor in organic chemistry. Its reactivity and functional groups make it suitable for various synthetic transformations, allowing the preparation of a range of quinoline-based derivatives with diverse applications in material science, agrochemicals, and other specialty chemical areas.

Upstream product

• 103772-12-9 ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 103772-10-7 2,3,4,5-tetrafluoro-6-nitro-benzoyl chloride 
• 103772-11-8 2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester 
• 104885-01-0 ethyl α-(ethoxymethylene)-2,3,4,5-tetrafluoro-6-nitro-β-oxobenzenepropanoate 
• 107564-02-3 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester 
• 602-94-8 Pentafluorobenzoic acid 
• 2251-50-5 pentafluorobenzoylchloride 
• 3516-87-8 ethyl 2,3,4,5,6-pentafluorobenzoylacetate 
• 114226-95-8 ethyl-2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate 
• 107564-01-2 ethyl 3-cyclopropylamino-2-pentafluorobenzoyl acrylate 
• 16583-08-7 2,3,4,5-tetrafluoro-6-nitrobenzoic acid 
• 110872-04-3 ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate 

Downstream Products

• 110871-85-7 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 111542-93-9 5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 110236-78-7 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid 
• 110871-86-8 sparfloxacin 
• 103772-14-1 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 

Relevant articles and documents

QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME

The present disclosure relates to quinolin-4-one and 4(1H)-cinnolinone compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β

The synthesis, GSK-3β inhibitory activity, and anti-microbial activity of bicyclic and tricyclic derivatives of the 5,7-diamino-6-fluoro-4-quinolone- 3-carboxylic acid scaffold were studied. Kinase selectivity profiling indicated that members of this class were potent and highly selective GSK-3 inhibitors.

Aminoquinolones as GSK-3 inhibitors

Provided herein are aminoquinolones and pharmaceutically acceptable derivatives thereof. In certain embodiments, provided herein are compounds, compositions and methods for treating, preventing or ameliorating GSK-3 mediated diseases.

Process for preparing a quinolone-carboxylic acid

The present invention provides a process for preparing quinolonecarboxylic acid derivatives having the formula (I): wherein R1 is H, halogen, or amino; R2 is halogen; R3 is H, halogen, C1-4 alkoxyl, or CN; R4 is selected from the group consisting of C3-6cycloalkyl, C1-4alkyl, C1-4alkoxyC1-4alkyl, and C1-4alkylaminoC1-4alkyl. The invention also provides new acetophenones having the formula (II) that are intermediates for preparing the compound of the formula (I).

Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship

A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and N1 (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.

Quinoline derivatives and processes for preparation thereof

The present invention relates to a quinoline derivative of the formula wherein Z is an amino group or a halogen atom, R1 is a hydrogen atom or a methyl or ethyl group, R2 is a hydrogen atom or a methyl or fluoromethyl group, R3 and R4 are the same or different and each represents a hydrogen atom or a methyl group, and n is 1 or 2; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents

Synthesis and Structure-Activity Relationships of 5-Substituted 6,8-Difluoroquinolones, Including Sparfloxacin, a New Quinolone Antibacterial Agent with Improved Potency

A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines.In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents.A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions.Compound 36k was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.

4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial agents

Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.