5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide

• ChemBase ID: 154272
• Molecular Formular: C17H14N2O4S
• Molecular Mass: 342.36906
• Monoisotopic Mass: 342.06742794
• SMILES: c1ccc(cc1)S(=O)(=O)Nc1cccc(c1)C#C/C=C/C(=O)NO
• Canonical SMILES: ONC(=O)/C=C/C#Cc1cccc(c1)NS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)
• InChIKey: QRPSQQUYPMFERG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide; (2E)-5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide
• IUPAC Traditional name: 5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide; (2E)-5-(3-benzenesulfonamidophenyl)-N-hydroxypent-2-en-4-ynamide
• Synonyms: (2E)-5-[3-(Phenylsulfonylamino)phenyl]-pent-2-en-4-ynohydroxamic acid; Oxamflatin; (2E)-N-Hydroxy-5-[3-[(phenylsulfonyl)amino]phenyl]-2-penten-4-ynamide; (2E)-5-[3-(Phenylsulfonylamino)phenyl]pent-2-en-4-ynohydroxamic Acid; Oxamflatin

Database IDs

• CAS Number: 151720-43-3
• MDL Number: MFCD00949087
• PubChem SID: 162248411
• PubChem CID: 5353852

CALCULATED PROPERTIES

• Acid pKa: 7.7770977
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.2027388
• LogD (pH = 7.4): 2.071371
• Log P: 2.2047713
• Molar Refractivity: 89.1108 cm^3
• Polarizability: 34.896065 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble13 mg/mL; Ethyl Acetate; Methanol
• Apperance: Red-Brown Solid; solid
• Melting Point: 98-100°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H14N2O4S

DETAILS

Sigma Aldrich - O3139

Biochem/physiol Actions
Histone deacetylase inhibitor; anti-cancer agent.

Toronto Research Chemicals - O845090

Histone deacetylase inhibitor. A cell-permeable, aromatic sulfonamide derivative with a hydroxamic acid group that potently inhibits mammalian HDAC by binding to the active site zinc.

REFERENCES

• Ohtani, M., et al.: J. Med. Chem., 39, 2871 (1996)
• Dear, A.E., et al.: Biochem. Biophys. Acta, 1492, 15 (1996)
• Lavoie, R., et al.: Bioorg. Med. Chem. Lett., 11, 2847 (1996)