3-methyl-4-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1λ6,4-thiomorpholine-1,1-dione

• ChemBase ID: 175010
• Molecular Formular: C10H13N3O5S
• Molecular Mass: 287.29232
• Monoisotopic Mass: 287.05759153
• SMILES: c1cc(oc1[N+](=O)[O-])/C=N/N1CCS(=O)(=O)CC1C
• Canonical SMILES: CC1CS(=O)(=O)CCN1/N=C/c1ccc(o1)[N+](=O)[O-]
• InChI: InChI=1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+
• InChIKey: ARFHIAQFJWUCFH-IZZDOVSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-4-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1λ^6,4-thiomorpholine-1,1-dione
• IUPAC Traditional name: nifurtimox
• Synonyms: 3-Methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-Dioxide; 4-(5-Nitrofurfurylideneamino)-3-methylthiomorpholine 1,1-Dioxide; BAY 2502; Bayer 2502; Lampit; (+/-)-Nifurtimox; Nifurtimox

Database IDs

• CAS Number: 23256-30-6
• PubChem SID: 164230920
• PubChem CID: 6842999

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.26584578
• LogD (pH = 7.4): -0.26584223
• Log P: -0.2658422
• Molar Refractivity: 66.782 cm^3
• Polarizability: 25.927639 Å^3
• Polar Surface Area: 108.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Orange Solid
• Melting Point: 177-183°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N458800

Antiprotozoal. Showing anti-Trypanosoma cruzi activity.

REFERENCES

• Letelier, M., et al.: Exp. Parasitol., 71, 357 (1990)
• Aguirre, G., et al.: Bioorg. Med. Chem., 12, 4885 (1990)
• Faundez, M., et al.: Antimicrob. Agents Chemother., 49, 126 (1990)
• Wang, Z., et al.: J. Med. Chem., 50, 3416 (1990)