268545-13-7

Basic information

• Product Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
• Synonyms: (4R,7R)-Moxifloxacin;1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid;ent-Moxifloxacin;3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-Methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-;Moxifloxacin isoMer;1-Cyclopropyl-6-fluoro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride;Moxifloxacin (R,R)-Isomer;(4R,7R)-Moxifloxacin Hydrochloride 2
• CAS NO: 268545-13-7
• Molecular Formula: C21H24FN3O4
• Molecular Weight: 401
• Product Categories: Chiral Reagents;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 268545-13-7.mol

Chemical Properties

• Melting Point: 226-228°C (dec.)
• Boiling Point: 636.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.408
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 6.43±0.50(Predicted)
• CAS DataBase Reference: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid(268545-13-7)
• EPA Substance Registry System: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid(268545-13-7)

Safety Data

• Hazardous Substances Data: 268545-13-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid is used as an active pharmaceutical ingredient (API) for the development of new drugs. Its unique molecular structure and chemical properties make it a promising candidate for targeting specific biological pathways and treating various diseases.
Used in Antimicrobial Applications:
In the pharmaceutical industry, 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid is used as an antimicrobial agent. It is particularly effective against mycobacterial infections, such as tuberculosis, due to its ability to inhibit bacterial growth and proliferation.
Used in Cytotoxic Applications:
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid is also used in the development of cytotoxic drugs, which are designed to target and destroy cancer cells. Its potential to modulate oncological signaling pathways and exert inhibitory effects on tumor growth and progression makes it a valuable asset in the fight against cancer.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid, novel drug delivery systems have been developed. These systems, which may include organic and metallic nanoparticles, aim to improve the compound's delivery to target cells and tissues, ultimately enhancing its efficacy in treating various diseases.

Upstream product

• 112811-72-0 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 151213-42-2 [R,R]-2,8-diazabicyclo[4.3.0]nonane 
• 128740-14-7 8-benzyl-2,8-diazabicyclo[4.3.0]nonane 
• 112811-70-8 ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate 
• 1028205-72-2 C₂₁H₂₅FN₄O₃ 
• 1028205-71-1 C₃₀H₄₁FN₄O₅ 
• 1028205-70-0 C₃₂H₃₇FN₄O₅ 
• 1028205-69-7 C₂₅H₃₃FN₄O₃ 
• 186826-86-8 moxifloxacin hydrochloride 
• 496919-99-4 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid O₃,O₄-bis(propyloxy-O)borate 

Downstream Products

• 721970-37-2 N-methylmoxifloxacin 
• 721970-35-0 methyl 1-cyclopropyl-6-fluoro-8-methoxy-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 925684-94-2 benzyl 7-((4aS,7aS)-1-(((4-(2,2-bis(diethylphosphono)ethyl)phenylcarbamoyl)methoxy)carbonyl)-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate 
• 925684-95-3 7-((4aS,7aS)-1-(((4-(2,2-bis(diethylphosphono)ethyl)phenylcarbamoyl)methoxy)carbonyl)-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925684-77-1 4-(bis(diethylphosphono)methyl)phenyl 7-((4aS,7aS)-1-(tert-butoxycarbonyl)-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate 
• 925684-31-7 7-((4aS,7aS)-1-(((4-(2,2-bisphosphonoethyl)phenylcarbamoyl)methoxy)carbonyl)-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925684-92-0 Benzyl 7-((4aS,7aS)-1-(tert-butoxycarbonyl)-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate 
• 925684-93-1 Benzyl 1-cyclopropyl-6-fluoro-1,4-dihydro-7-((4aS,7aS)-octahydropyrrolo[3,4-b]pyridin-6-yl)-8-methoxy-4-oxoquinoline-3-carboxylate 

Relevant articles and documents

Preparation method of moxifloxacin

The invention provides a preparation method of moxifloxacin, which comprises the following steps: taking 1-cyclopropyl-6, 7-difluoro-8-methoxy-4-oxo-1, 4-dihydro-3-quinolinecarboxylic acid and (S, S)-2, 8-diazabicyclo[4.3. 0] nonane as raw materials, in an organic solvent, in the presence of an acid-binding agent, and carrying out condensation reaction by taking the tri-coordinated boride cation-chloroaluminate ionic liquid as a catalyst to prepare moxifloxacin. The structural formula of the tri-coordinated boride cation-chloroaluminate ionic liquid is BX2L, X is a halogen atom, and L is selected from 4-picoline (4-pic), imidazole (mim) and dimethylacetamide (DMA) ligands. The preparation method of moxifloxacin has the advantages of simple reaction steps, high yield, high product purity, mild conditions and easiness in industrial production.

Polymer-Based Bioorthogonal Nanocatalysts for the Treatment of Bacterial Biofilms

Bioorthogonal catalysis offers a unique strategy to modulate biological processes through the in situ generation of therapeutic agents. However, the direct application of bioorthogonal transition metal catalysts (TMCs) in complex media poses numerous challenges due to issues of limited biocompatibility, poor water solubility, and catalyst deactivation in biological environments. We report here the creation of catalytic "polyzymes", comprised of self-assembled polymer nanoparticles engineered to encapsulate lipophilic TMCs. The incorporation of catalysts into these nanoparticle scaffolds creates water-soluble constructs that provide a protective environment for the catalyst. The potential therapeutic utility of these nanozymes was demonstrated through antimicrobial studies in which a cationic nanozyme was able to penetrate into biofilms and eradicate embedded bacteria through the bioorthogonal activation of a pro-antibiotic.

Nano-Fe3 O4@ZrO2-SO3 H as highly efficient recyclable catalyst for the green synthesis of fluoroquinolones

Nano-Fe3 O4 @ZrO2-SO3 H (n-FZSA), was utilized as a magnetic catalyst for the synthesis of various fluoroquinolone compounds. These compounds were prepared by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b] pyridine in water. The results showed that n-FZSA exhibited high catalytic activity towards the synthesis of fluoroquinolone derivatives, giving the desired products in high yields. Furthermore, the catalyst was recyclable and could be used at least seven times without any discernible loss in its catalytic activity. Overall, this new catalytic method for the synthesis of fluoroquinolone derivatives provides rapid access to the desired compounds in refluxing water following a simple work-up procedure, and avoids the use of organic solvents.

Conventional and microwave-assisted synthesis of quinolone carboxylic acid derivatives

Various antibacterial fluoroquinolone compounds are synthesized by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with a variety of piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine using microwave under different reaction conditions. Solvent free high yield microwave synthesis of antibacterial fluoroquinolone compounds is convenient, rapid and environmentally friendly method.

Fluorescence quenching study of moxifloxacin interaction with calf thymus DNA

Moxi oxacin (MOX) is a fourth-generation synthetic uoroquinolone antibacterial agent with many important therapeutic properties. Fluorescence quenching was used to study the interaction of MOX with calf thymus DNA (ct- DNA) in aqueous solution. The intercalative binding mode and a static quenching mechanism were conflrmed by the Stern-Volmer quenching rate constant (Kq) of 3.48 × 1011 M-1 s-1 at 298 K. The thermodynamic parameters (δH = -118.4 KJ mol-1 and δS = -299.4 J mol-1 K-1) were calculated at different temperatures, and they indicate that the main forces between MOX and ct-DNA are hydrogen bonding and Van der Waals force. We proved at the same time the presence of one single binding site on ct-DNA, and the binding constant is 1.28 × 105 M-1 at physiological pH. The results may provide a basis for further studies and clinical application of antibiotics drugs. Tubitak.

IR, FT-ICR-MS studies on (1′S, 6′S)-1-cyclopropyl-7-(2,8- diazabicyclo[4.3.0] non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid hydrochloride salt

The infrared spectra of (1′S, 6′S)-1-cyclopropyl-7-(2,8- diazabicyclo[4.3.0] non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid hydrochloride salt (CLF-HCl) were studied and compared with free base. Their fragmentation pathways were investigated using tandem mass spectrometric (MS/MS) techniques on Fourier-transform ion cyclotron resonance spectrum, and many characteristic fragment ions were found.

Process for the preparation of moxifloxacin hydrochloride and intermediates thereof

The present invention refers to a process for the preparation of Moxifloxacin hydrochloride through the synthesis of Moxifloxacin salts with sulfonic acids.

MOXIFLOXACIN HYDROCHLORIDE COMPOUNDS AND INTERMEDIATES AND METHODS FOR MAKING SAME

Methods for producing moxifloxacin hydrochloride compounds having very low levels of impurities are provided. Compounds produced using such methods and pharmaceutical compositions including such compounds are also provided.

Process for the Synthesis of Moxifloxacin Hydrochloride

A new polymorph of moxifloxacin hydrochloride is described, together with a method for making the polymorph. In addition, new intermediates in the formation of moxifloxacin hydrochloride are described, having formulas (1) and (II):

IMPROVED PROCESS FOR THE PREPARATION OF (S.S)-2.8-DIAZABICYCLO[4.3.0]NONANE

The present invention is directed to an improved industrially viable, cost effective process for manufacturing (S,S)-2,8-Diazabicyclo[4.3.0]nonane in a substantially pure form and consequent conversion to Moxifloxacin hydrochloride monohydrate.