| Identification | Back Directory | [Name]
(S)-(-)-Nadifloxacin | [CAS]
154357-42-3 | [Synonyms]
LEVONADIFLOXACIN
(S)-(-)-OPC-7251
(S)-(-)-Nadifloxacin
Nadifloxacin (S)-Isomer
Nadifloxacin Impurity 5
Nadifloxacin impurities1236
JYJTVFIEFKZWCJ-JTQLQIEISA-N
(S)-(-)-Nadifloxacin USP/EP/BP
Nadifloxacin Impurity 5 (S-Nadifloxacin)
(4S)-1-Oxo-4β-methyl-5,6-dihydro-7-(4-hydroxypiperidino)-8-fluoro-4H-3a-aza-1H-phenalene-2-carboxylic acid
(5S)-9-Fluoro-6,7-dihydro-8-(4-hydroxypiperidino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (S)-
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (5S)-
(S)-9-Fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (5S)- (9CI) | [Molecular Formula]
C19H21FN2O4 | [MDL Number]
MFCD09954130 | [MOL File]
154357-42-3.mol | [Molecular Weight]
360.38 |
| Chemical Properties | Back Directory | [Boiling point ]
624.9±55.0 °C(Predicted) | [density ]
1.46 | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : 125 mg/mL (346.86 mM; Need ultrasonic) | [form ]
Solid | [pka]
5.55±0.40(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
(S)-(-)-Nadifloxacin is an anti-bacterial agent against multidrug-resistant Staphylococcus aureus. Also, it is derived from 6-Fluoro-2-methylquinoline (F595900), which is an quinoline derivative, a highly potent thrombin receptor antagonist. | [Definition]
ChEBI: (S)-nadifloxacin is a nadifloxacin. It is an enantiomer of a (R)-nadifloxacin. | [Biological Activity]
Levonadifloxacin is a potent benzoquinolizine fluoroquinolone antibiotic th at is affective against Gram-positive and Gram-negative bacteriaincluding methicillin- and quinolone-resistant Staphylococcus aureusStreptococcus pneumoniaeStreptococcus pyogenesHaemophilus influenzaeand Moraxella catarrhalis and atypical pathogens. It appears th at Levonadifloxacin targets staphylococcal DNA gyraseunlike other quinoloneswhich primarily inhibit DNA topoisomerase IV. | [Synthesis]
Starting from 2-bromo-4,5-difluoroacetylaniline, it was reacted with crotonaldehyde under Skraup-Doeber-VonMiller reaction conditions to generate quinoline 2 in 67% yield. Pd-on-carbon catalytic hydrogenation was used to reduce the carbon-bromine bond in 2, and the catalyst was removed by filtration. Platinum-on-carbon was added to the reaction mixture and the hydrogenation conditions were again applied to give tetrahydroquinoline 3 in 97% yield. Tetrahydroquinoline 3 was reacted with 2,3-di-O-benzyl-L-tartaric acid (L-DBTA) and subsequently recrystallized from 60% methanol-water solution to give S-isomer 4 in 35% yield and 100% enantiomeric excess. The recovered R-isomer could be racemized by treatment with methanesulfonic acid. Compound 4 was reacted with diethylethoxymethylvinylmalonate in polyphosphoric acid and subsequently treated with hydrochloric acid to give tricyclic acid 5 in 88% yield. The tricyclic acid 5 chelates with the in situ generated borotriacetate to form the cyclic boronic ester complex 6. The cyclic boronic ester complex 6 is reacted with 4-hydroxypiperidine to afford levonadifloxacin 8 in good yield in a two-step reaction.
| [Mechanism of action]
Levofloxacin is a fluoroquinolone antibiotic that works by inhibiting bacterial DNA gyrase.
| [Advantages]
(S)-(-)-Nadifloxacin is 60-250 times more potent than its R-isomer, nadifloxacin.
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| Company Name: |
Lewens Labs
|
| Tel: |
+917043057100 |
| Website: |
www.lewenslabs.com |
| Company Name: |
LGM Pharma
|
| Tel: |
1-(800)-881-8210 |
| Website: |
www.lgmpharma.com |
|