(6S)-2-nitro-6-{[4-(trifluoromethoxy)phenyl]methoxy}-5H,6H,7H-imidazo[2,1-b][1,3]oxazine

• ChemBase ID: 128789
• Molecular Formular: C14H12F3N3O5
• Molecular Mass: 359.2573896
• Monoisotopic Mass: 359.07290516
• SMILES: [O-][N+](=O)c1cn2C[C@@H](COc2n1)OCc1ccc(OC(F)(F)F)cc1
• Canonical SMILES: [O-][N+](=O)c1cn2c(n1)OC[C@H](C2)OCc1ccc(cc1)OC(F)(F)F
• InChI: InChI=1S/C14H12F3N3O5/c15-14(16,17)25-10-3-1-9(2-4-10)7-23-11-5-19-6-12(20(21)22)18-13(19)24-8-11/h1-4,6,11H,5,7-8H2/t11-/m0/s1
• InChIKey: ZLHZLMOSPGACSZ-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-2-nitro-6-{[4-(trifluoromethoxy)phenyl]methoxy}-5H,6H,7H-imidazo[2,1-b][1,3]oxazine
• IUPAC Traditional name: (6S)-2-nitro-6-{[4-(trifluoromethoxy)phenyl]methoxy}-5H,6H,7H-imidazo[2,1-b][1,3]oxazine
• Synonyms: PA 824; (6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine; (S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine; PA 824; (S)-PA 824

Database IDs

• CAS Number: 187235-37-6
• PubChem SID: 162223093
• PubChem CID: 456199
• CHEMBL: 227875
• MeSH Name: PA+824
• Wikipedia Title: PA_824

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 4.1363235
• LogD (pH = 7.4): 4.1363235
• Log P: 4.1363235
• Molar Refractivity: 73.9118 cm^3
• Polarizability: 28.759819 Å^3
• Polar Surface Area: 91.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P122500

A novel anti-tuberculosis drug.

REFERENCES

• Diacon, A.H. et al.: Antimicrob. Anents Chemother., 54, 3402 (2010)
• Dogra, M. et al.: Br. J. Pharmacol., 162, 226 (2010)
• Ginsberg, A.M. et al.: Antimicrob. Agents Chemother., 53, 3720 (2010)