N-{5-[(4-methoxyphenyl)methyl]-1,3,4-thiadiazol-2-yl}benzenesulfonamide

• ChemBase ID: 154309
• Molecular Formular: C16H15N3O3S2
• Molecular Mass: 361.4386
• Monoisotopic Mass: 361.05548336
• SMILES: COc1ccc(cc1)Cc1nnc(s1)NS(=O)(=O)c1ccccc1
• Canonical SMILES: COc1ccc(cc1)Cc1nnc(s1)NS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C16H15N3O3S2/c1-22-13-9-7-12(8-10-13)11-15-17-18-16(23-15)19-24(20,21)14-5-3-2-4-6-14/h2-10H,11H2,1H3,(H,18,19)
• InChIKey: QCXWBMZVLJCKHF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{5-[(4-methoxyphenyl)methyl]-1,3,4-thiadiazol-2-yl}benzenesulfonamide
• IUPAC Traditional name: N-{5-[(4-methoxyphenyl)methyl]-1,3,4-thiadiazol-2-yl}benzenesulfonamide
• Synonyms: N-[5-(4-Methoxybenzyl)-1,3,4-thiadiazol-2-yl]benzenesulfonamide; OU749

Database IDs

• CAS Number: 519170-13-9
• MDL Number: MFCD03351667
• PubChem SID: 162248448
• PubChem CID: 2177065

CALCULATED PROPERTIES

• Acid pKa: 6.5700154
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.688659
• LogD (pH = 7.4): 2.078258
• Log P: 2.7199404
• Molar Refractivity: 93.3205 cm^3
• Polarizability: 36.02458 Å^3
• Polar Surface Area: 81.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H15N3O3S2

DETAILS

Sigma Aldrich - O8890

Biochem/physiol Actions
Gamma-glutamyl transpeptidase (GGT; aka gamma-glutamyl transferase) cleaves the gamma-glutamyl bond of glutathione, making extracellular glutathione available for intracellular use. Elevated intracellular glutathione contributes to resistance of tumors to chemotherapy and radiation. GGT is a therapeutic target for treatment-resistance cancers, as treatment with GGT inhibitors prior to chemotherapy or radiation could sensitize GGT-positive tumors to treatment by decreasing glutathione levels. Previously, all GGT inhibitors have been glutamine analogues, which are competitive for the gamma-glutamyl site. Due to high toxicity, these compounds cannot be used in the clinic. OU749 is the first non-glutamine GGT inhibitor. It is also non-competitive for the gamma-glutamyl site. OU749 inhibits human GGT in an enzyme assay and is much less toxic than other GGT inhibitors, including azaserine (glutamine analogue, Sigma catalog).