3-amino-5-(thiophen-3-yl)thiophene-2-carboxamide

• ChemBase ID: 177644
• Molecular Formular: C9H8N2OS2
• Molecular Mass: 224.30262
• Monoisotopic Mass: 224.00780489
• SMILES: c1cscc1c1sc(c(c1)N)C(=O)N
• Canonical SMILES: NC(=O)c1sc(cc1N)c1cscc1
• InChI: InChI=1S/C9H8N2OS2/c10-6-3-7(5-1-2-13-4-5)14-8(6)9(11)12/h1-4H,10H2,(H2,11,12)
• InChIKey: BMUACLADCKCNKZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-5-(thiophen-3-yl)thiophene-2-carboxamide
• IUPAC Traditional name: 3-amino-5-(thiophen-3-yl)thiophene-2-carboxamide
• Synonyms: 5-(Thien-3-yl)-3-aminothiophene-2-carboxamide; 4-Amino-[2,3'-bithiophene]-5-carboxamide; SC-514

Database IDs

• CAS Number: 354812-17-2
• PubChem SID: 164233554
• PubChem CID: 2807869

CALCULATED PROPERTIES

• Acid pKa: 15.250212
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.9822149
• LogD (pH = 7.4): 1.9822149
• Log P: 1.9822149
• Molar Refractivity: 58.7528 cm^3
• Polarizability: 22.575272 Å^3
• Polar Surface Area: 69.11 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 209-211°C

Pharmacology Properties

• Target: IKK; IκB

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - S199900

A cell-permeable (thienothienyl)amino-acetamide compound that displays anti-inflammatory properties. Acts as a potent, reversible, ATP-competitive, and highly selective inhibitor of IKK-2 (IC50 ~3-12 μM for IKK-2 homodimer, IKK-1/IKK-2 heterodimer, and IKK-2). Its specificity has been confirmed using a panel of 31 other kinases, including IKK isoforms IKK-1, IKK-i, and TBK-1 (IC50 > 200 μM). Shown to specifically block NF-kB-dependent gene expression, but not MAP kinase pathways, in stimulated synovial fibroblasts RASF.

REFERENCES

• Kishore, N., et al.: J. Biol. Chem., 278, 32861 (2003)