138808-76-1

Basic information

• Product Name: 1-CYCLOPROPYL-6-FLUORO-7-((1R,4R)-5-METHYL-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL)-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID
• Synonyms: 1-CYCLOPROPYL-6-FLUORO-7-((1R,4R)-5-METHYL-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL)-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID;3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(5-Methyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-4-oxo-, (1R)- (9CI)
• CAS NO: 138808-76-1
• Molecular Formula: C₁₉H₂₀FN₃O₃
• Molecular Weight: 0
• Mol File: 138808-76-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 569.3°C at 760 mmHg
• Flash Point: 298.1°C
• Appearance: /
• Density: 1.485g/cm³
• Vapor Pressure: 8.41E-14mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 1-CYCLOPROPYL-6-FLUORO-7-((1R,4R)-5-METHYL-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL)-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYCLOPROPYL-6-FLUORO-7-((1R,4R)-5-METHYL-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL)-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID(138808-76-1)
• EPA Substance Registry System: 1-CYCLOPROPYL-6-FLUORO-7-((1R,4R)-5-METHYL-2,5-DIAZA-BICYCLO[2.2.1]HEPT-2-YL)-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID(138808-76-1)

Safety Data

• Hazardous Substances Data: 138808-76-1(Hazardous Substances Data)

Usage

Chemical Class

Quinolone antibiotic

Explanation

Different sources of media describe the Explanation of 138808-76-1 differently. You can refer to the following data:
1. A type of broad-spectrum antibiotic that inhibits bacterial DNA replication.
2. These groups are part of the compound's structure and contribute to its pharmacological activity.
3. The stereochemistry of the compound, which refers to the spatial arrangement of its atoms, is important for its biological activity.
4. The carboxylic acid group is a key functional group in the compound, which can participate in various chemical reactions and interactions.
5. The compound has potential pharmaceutical applications, particularly in the development of new antibiotics to combat bacterial infections.
6. The compound is of interest for the development of new antibiotics to treat bacterial infections, which are a significant health concern worldwide.
7. The development of new antibiotics, such as this compound, is crucial in the fight against antibiotic resistance, a growing global health threat.
8. The compound's unique structure, including its cyclopropyl, fluorine, bicyclic heptane, and carboxylic acid groups, is responsible for its pharmacological activity and potential as an antibiotic.

Structure

Cyclopropyl and fluorine groups

Stereochemistry

(1R,4R)-5-Methyl-2,5-diazabicyclo[2.2.1]hept-2-yl

Bicyclic Heptane

Part of the compound's structure

Functional Group

Carboxylic acid

Potential Applications

Pharmaceutical development

Mechanism of Action

Inhibition of bacterial DNA replication

Target

Bacterial infections

Research Focus

Combating antibiotic resistance

Structure-Activity Relationship

Specific structure contributes to pharmacological activity

InChI:InChI=1/C19H20FN3O3/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/t11-,12-/m1/s1

Upstream product

• 93107-30-3 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 133097-95-7 (1R,4R)-2-Methyl-2,5-diazabicyclo<2.2.1>heptane 

Relevant articles and documents

Synthesis and structure-activity relationships of 7- diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine

A series of novel 6-fluoro-7-diazabicycloalkylquinolonecarboxylic acids substituted with various C8 (H, F, Cl, N) and N1 (ethyl, cyclopropyl, vinyl, 2-fluoroethyl, 4-fluorophenyl, 2,4-difluorophenyl) substituents, as well as, 9-fluoro-10-diazabicycloalkylpyridobenzoxazinecarboxylic acids, were prepared and evaluated for antibacterial activity against a range of important veterinary pathogenic bacteria. The diazabicycloalkyl side chains investigated at the 7-position (benzoxazine 10-position) include (1S,4S)-5- methyl-2,5-diazabicyclo[2.2.1]heptane (2), (1S,4S)-2,5- diazabicyclo[2.2.1]heptane (3), (1R,4R)-5-methyl-2,5- diazabicyclo[2.2.1]heptane (4), 8-methyl-3,8-diazabicyclo[3.2.1]octane (5), 9-methyl-3,9-diazabicyclo[4.2.1]nonane (6), 1,4-diazabicyclo[3.2.2]nonane (7), 1,4-diazabicyclo[3.3.1]nonane (8), and 9-methyl-3,9- diazabicyclo[3.3.1]nonane (9). Among these side chains, in vitro potency was not highly variable; other properties therefore proved more critical to the selection of possible development candidates. However, the relative potencies observed for several of these compounds in mouse, swine, and cattle infection models correlated well with those seen in vitro. A combination of the N1 cyclopropyl group and the C7 (1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2- yl appendage conferred the best overall antibacterial, physiochemical, and pharmacodynamic properties. Hence, danofloxacin (Advocin, 2c) (originally CP- 76,136, 1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5- diazabicyclo[2.2.1]hept-2-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid) was selected as a candidate for development as a therapeutic antibacterial agent for veterinary medicine.