Compound ID | 2436

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Tricyclic-2-quinolone 25

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: DNA synthesis inhibitor. Bacterial topoisomerase inhibitor
Target Pathogen: Active against fluoroquinolone-resistant and -susceptible Staphylococcus aureus
Description: Synthetic compound; analogues reported
Institute where first reported: Novartis Institutes for BioMedical Research, Emeryville, California 94608, United States
Year first mentioned: 2021
Development status: Experimental
Chemical structure(s):
Compound 25
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Molecular weight: 387.41
Iso. SMILES: C[C@H]1COC2=C3N1C(=O)C(=CC3=CC(=C2N4CC[C@H](C4)C5(CC5)N)F)C(=O)O
InChI Key: KUJKUYSIFHKKCZ-CMPLNLGQSA-N
Can. SMILES: C[C@H]1COC2=C(C(=CC3=C2N1C(=O)C(=C3)C(=O)O)F)N4CC[C@H](C4)C5(CC5)N
InChI: InChI=1S/C20H22FN3O4/c1-10-9-28-17-15-11(6-13(19(26)27)18(25)24(10)15)7-14(21)16(17)23-5-2-12(8-23)20(22)3-4-20/h6-7,10,12H,2-5,8-9,22H2,1H3,(H,26,27)/t10-,12+/m0/s1
Compound 55
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Molecular weight: 437.41
Iso. SMILES: FC1=C(C=2OC[C@H](C)N3C2C(C=C(C3=O)C(O)=O)=C1)N4C[C@]5(CC(F)(F)C[C@@H](N)[C@@]5([H])C4)[H]
InChI Key: RSDFGTPMONMMRE-XPGAZNKBSA-N
Can. SMILES: C[C@H]1COC2=C(C(=CC3=C2N1C(=O)C(=C3)C(=O)O)F)N4C[C@@]5([H])CC(C[C@H]([C@@]5([H])C4)N)(F)F
InChI: InChI=1S/C21H22F3N3O4/c1-9-8-31-18-16-10(2-12(20(29)30)19(28)27(9)16)3-14(22)17(18)26-6-11-4-21(23,24)5-15(25)13(11)7-26/h2-3,9,11,13,15H,4-8,25H2,1H3,(H,29,30)/t9-,11+,13-,15+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135369812
Citation: https://pubs.acs.org/doi/10.1021/acs.jmedchem.1c00375
Patent: US2018318311A1

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