Compound ID | 2842

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Tricyclic amide NBTI (N-(2-((9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)methyl)- trans -1,3-dioxan-5-yl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxamide)

Synonym(s): Azatricyclic amide-linked pyridooxazinone (1a)

Class: DNA synthesis inhibitor

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against methicillin-resistant Staphylococcus aureus, Acinetobacter baumannii, and Escherichia coli; bacterial topoisomerase inhibitor; targets DNA gyrase and topoisomerase IV
Description: Synthetic compound; derived from a tricyclic amine NBTI (2a) which only showed Gram-positive activity, poor hERG inhibition (relates cardiac toxicity) and metabolic stability; shows in vitro cardiac safety (common issue in NBTIs) and extended antibiotic spectrum; additionally inhibits human leukaemia K562 cells
Institute where first reported: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA
Year first mentioned: 2023
Development status: Experimental
Chemical structure(s):
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Molecular weight: 482.46
Iso. SMILES: O=C1C=CC2C3N1CC(C[C@@H]4OC[C@@H](NC(C5=CC=C6OCC(NC6=N5)=O)=O)CO4)C3=C(F)C=C2
InChI Key: RLOSKSQMAFQGST-YPLOAFKNSA-N
Can. SMILES: C1=CC(=C2C(C[C@H]3OC[C@@H](CO3)NC(=O)C4=CC=C5C(=N4)NC(=O)CO5)CN6C(=O)C=CC1C26)F
InChI: InChI=1S/C24H23FN4O6/c25-15-3-1-12-2-6-19(31)29-8-13(21(15)22(12)29)7-20-34-9-14(10-35-20)26-24(32)16-4-5-17-23(27-16)28-18(30)11-33-17/h1-6,12-14,20,22H,7-11H2,(H,26,32)(H,27,28,30)/t12?,13?,14-,20-,22?
External links:
Citations:
  • https://pubs.acs.org/doi/10.1021/acsmedchemlett.2c00111
  • https://journals.asm.org/doi/10.1128/aac.00482-23

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