6-chloro-4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ6,5,2-thieno[2,3-e][1λ6,2]thiazine-3-carboxamide

• ChemBase ID: 164328
• Molecular Formular: C12H10ClN3O4S3
• Molecular Mass: 391.8735
• Monoisotopic Mass: 390.9521965
• SMILES: C1(=C(c2c(S(=O)(=O)N1C)cc(s2)Cl)O)C(=O)Nc1ncc(s1)C
• Canonical SMILES: Cc1cnc(s1)NC(=O)C1=C(O)c2sc(cc2S(=O)(=O)N1C)Cl
• InChI: InChI=1S/C12H10ClN3O4S3/c1-5-4-14-12(21-5)15-11(18)8-9(17)10-6(3-7(13)22-10)23(19,20)16(8)2/h3-4,17H,1-2H3,(H,14,15,18)
• InChIKey: MXKICRYCQXZDES-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ^6,5,2-thieno[2,3-e][1λ^6,2]thiazine-3-carboxamide
• IUPAC Traditional name: 6-chloro-4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ^6,5,2-thieno[2,3-e][1λ^6,2]thiazine-3-carboxamide
• Synonyms: 6-Chloro-4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-Dioxide

Database IDs

• CAS Number: 479482-38-7
• PubChem SID: 162258463
• PubChem CID: 54689453

CALCULATED PROPERTIES

• Acid pKa: 2.0238187
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.46148303
• LogD (pH = 7.4): -0.5450295
• Log P: 2.1356063
• Molar Refractivity: 89.4795 cm^3
• Polarizability: 33.982365 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C366640

Used in the preparation of hydroxythienothiazinecarboxamidedioxides as anti-inflammatory agents, analgesics, and antirheumatic agents.

REFERENCES

• Fu, J.Y., et al.: J. Biol. Chem., 265, 16737 (1990)
• Berg, J., et al.: Inflamm. Res., 48, 369 (1990)