138808-76-1 Usage
Chemical Class
Quinolone antibiotic
Explanation
A type of broad-spectrum antibiotic that inhibits bacterial DNA replication.
Explanation
These groups are part of the compound's structure and contribute to its pharmacological activity.
Explanation
The stereochemistry of the compound, which refers to the spatial arrangement of its atoms, is important for its biological activity.
Explanation
The carboxylic acid group is a key functional group in the compound, which can participate in various chemical reactions and interactions.
Explanation
The compound has potential pharmaceutical applications, particularly in the development of new antibiotics to combat bacterial infections.
Explanation
The compound is of interest for the development of new antibiotics to treat bacterial infections, which are a significant health concern worldwide.
Explanation
The development of new antibiotics, such as 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, is crucial in the fight against antibiotic resistance, a growing global health threat.
Explanation
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
Check Digit Verification of cas no
The CAS Registry Mumber 138808-76-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,8,0 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 138808-76:
(8*1)+(7*3)+(6*8)+(5*8)+(4*0)+(3*8)+(2*7)+(1*6)=161
161 % 10 = 1
So 138808-76-1 is a valid CAS Registry Number.
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
138808-76-1Relevant academic research and scientific papers
Synthesis and structure-activity relationships of 7- diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine
McGuirk,Jefson,Mann,Elliott,Chang,Cisek,Cornell,Gootz,Haskell,Hindahl,LaFleur,Rosenfeld,Shryock,Silvia,Weber
, p. 611 - 620 (2007/10/02)
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.
