ABT-719 - CAS 162829-90-5
Catalog number: 162829-90-5
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C18H20FN3O3
Molecular Weight:
345.23
COA:
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Targets:
Topoisomerase
Description:
ABT-719, a fluoroquinolone derivative, has been found to be a DNA topoisomerase inhibitor that was once developed in antibacterial studies.
Purity:
98%
Appearance:
Powder
Synonyms:
ABT-719; ABT719; ABT 719; ABT-719; A-816719.1; A 816719.1; A816719.1; (R)-8-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
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Quality Standard:
In-house standard
Quantity:
Milligram-Grams
InChIKey:
AUUKUAHPMHVZJL-NSHDSACASA-N
InChI:
InChI=1S/C18H20FN3O3/c1-9-15-12(10-2-3-10)6-13(18(24)25)17(23)22(15)8-14(19)16(9)21-5-4-11(20)7-21/h6,8,10-11H,2-5,7,20H2,1H3,(H,24,25)/t11-/m0/s1
Canonical SMILES:
CC1=C(C(=CN2C1=C(C=C(C2=O)C(=O)O)C3CC3)F)N4CCC(C4)N
1.Synthesis and antimicrobial activity of 4H-4-oxoquinolizine derivatives: consequences of structural modification at the C-8 position.
Ma Z;Chu DT;Cooper CS;Li Q;Fung AK;Wang S;Shen LL;Flamm RK;Nilius AM;Alder JD;Meulbroek JA;Or YS J Med Chem. 1999 Oct 7;42(20):4202-13.
The antibacterial 4H-4-oxoquinolizines were introduced recently to overcome bacterial resistance to fluoroquinolones. They exhibit potent antibacterial activity against Gram-positive, Gram-negative, and anaerobic organisms and are highly active against some quinolone-resistant bacteria including quinolone-resistant MRSA. Preliminary studies indicated that oxoquinolizines possess distinct activity and toxicity profiles as compared with their parent quinolones. In order to develop a potent antibacterial agent with the desired spectrum of activity, good tolerability, and balanced pharmacokinetic profile, we synthesized and evaluated a series of oxoquinolizines with various substituents at the C-8 position. Most compounds tested in this study demonstrated better activity against Gram-positive bacteria than ciprofloxacin and exhibited good susceptibility against ciprofloxacin- and methicillin-resistant S. aureus. While maintaining potent in vitro activity, several compounds showed improved in vivo efficacy over ABT-719 as indicated by the mouse protection test. As an example, the oral ED(50) values for the cis-3-amino-4-methylpiperidine analogue 3ss against S. aureus NCTC 10649M, S. pneumoniae ATCC 6303, and E.
2.DNA cleavage activities of Staphylococcus aureus gyrase and topoisomerase IV stimulated by quinolones and 2-pyridones.
Saiki AY;Shen LL;Chen CM;Baranowski J;Lerner CG Antimicrob Agents Chemother. 1999 Jul;43(7):1574-7.
We have cloned Staphylococcus aureus DNA gyrase and topoisomerase IV and expressed them in Escherichia coli as polyhistidine-tagged proteins to facilitate purification and eliminate contamination by host enzymes. The enzyme preparations had specific activities similar to previously reported values. Potassium glutamate (K-Glu) stimulated the drug-induced DNA cleavage activity and was optimal between 100 and 200 mM for gyrase and peaked at 100 mM for topoisomerase IV. Higher concentrations of K-Glu inhibited the cleavage activities of both enzymes. Using a common buffer system containing 100 mM K-Glu, we tested the enzyme-mediated DNA cleavage activities of both gyrase and topoisomerase IV with oxolinic acid, norfloxacin, ciprofloxacin, trovafloxacin, clinafloxacin, and the 2-pyridone ABT-719. As expected, all drugs tested demonstrated greater potency against topoisomerase IV than against gyrase. In addition, cleavage activity was found to correlate well with antibacterial activity.
3.Synthesis and structure-activity relationships of 2-pyridones: a novel series of potent DNA gyrase inhibitors as antibacterial agents.
Li Q;Chu DT;Claiborne A;Cooper CS;Lee CM;Raye K;Berst KB;Donner P;Wang W;Hasvold L;Fung A;Ma Z;Tufano M;Flamm R;Shen LL;Baranowski J;Nilius A;Alder J;Meulbroek J;Marsh K;Crowell D;Hui Y;Seif L;Melcher LM;Plattner JJ J Med Chem. 1996 Aug 2;39(16):3070-88.
Two novel series of 2-pyridones were synthesized by transposition of the nitrogen of 4-quinolones to the bridgehead position. This subtle interchange of the nitrogen atom with a carbon atom yielded two novel heterocyclic nuclei, pyrido[1,2-alpha]pyrimidine and quinolizine, which had not previously been evaluated as antibacterial agents and were found to be potent inhibitors of DNA gyrase. Quinolizines with a methyl group at the 9-position such as (S)-45a (ABT-719) demonstrate exceptional broad spectrum antibacterial activity. Most notably, they are active against resistant bacteria such as methicillin-resistant Staphylococcus aureus, vancomycin-resistant strains of enterococci, and ciprofloxacin-resistant organisms. In addition, 2-pyridones also possess favorable physiochemical and pharmacokinetic properties. These 2-pyridones were synthesized from the commercially available starting materials by 10-17 linear transformations. The structure of an adduct yielded by this sequence, (S)-45a (ABT-719), was determined by X-ray crystallographic analysis.
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