2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-1-(3,4-dihydroxyphenyl)ethan-1-one hydrochloride

• ChemBase ID: 154425
• Molecular Formular: C11H12ClNO3S2
• Molecular Mass: 305.80088
• Monoisotopic Mass: 304.99471293
• SMILES: c1cc(c(cc1C(=O)CSC1=NCCS1)O)O.Cl
• Canonical SMILES: O=C(c1ccc(c(c1)O)O)CSC1=NCCS1.Cl
• InChI: InChI=1S/C11H11NO3S2.ClH/c13-8-2-1-7(5-9(8)14)10(15)6-17-11-12-3-4-16-11;/h1-2,5,13-14H,3-4,6H2;1H
• InChIKey: ZZAVDVMJZKDBIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-1-(3,4-dihydroxyphenyl)ethan-1-one hydrochloride
• IUPAC Traditional name: 2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-1-(3,4-dihydroxyphenyl)ethanone hydrochloride
• Synonyms: 2-(4,5-Dihydro-1,3-thiazol-2-ylthio)-1-(3,4-dihydroxyphenyl)ethanone hydrochloride; Reactivation of Transcriptional Reporter Activity; RETRA

Database IDs

• MDL Number: MFCD11114394
• PubChem SID: 162248564
• PubChem CID: 46861546

CALCULATED PROPERTIES

• Acid pKa: 7.8630924
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.1651373
• LogD (pH = 7.4): 2.042552
• Log P: 2.1699836
• Molar Refractivity: 70.8269 cm^3
• Polarizability: 27.008678 Å^3
• Polar Surface Area: 69.89 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H12ClNO3S2

DETAILS

Sigma Aldrich - R1906

Biochem/physiol Actions
RETRA is a mutant p53-dependent activator of p73, an activator of p53-regulated genes, and a suppressor of mutant p53-bearing tumor cells. Greater than 50% of tumors express mutant p53 which is defective for the tumor-suppressor function and contributes to malignancy by blocking a p53 family member p73. Activation of p73 in human cancer produces a cytotoxic effect. RETRA increases expression level of p73 and releases p73 from the inhibitory complex with mutant 53. It thereby produces tumor-supressor effect, in vitro and in vivo, similar to functional reactivation of p53.