5-chloro-N-[4-methoxy-3-(piperazin-1-yl)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide hydrochloride

• ChemBase ID: 154663
• Molecular Formular: C20H23Cl2N3O3S2
• Molecular Mass: 488.45092
• Monoisotopic Mass: 487.05578897
• SMILES: Cc1c2cc(ccc2sc1S(=O)(=O)Nc1ccc(c(c1)N1CCNCC1)OC)Cl.Cl
• Canonical SMILES: COc1ccc(cc1N1CCNCC1)NS(=O)(=O)c1sc2c(c1C)cc(cc2)Cl.Cl
• InChI: InChI=1S/C20H22ClN3O3S2.ClH/c1-13-16-11-14(21)3-6-19(16)28-20(13)29(25,26)23-15-4-5-18(27-2)17(12-15)24-9-7-22-8-10-24;/h3-6,11-12,22-23H,7-10H2,1-2H3;1H
• InChIKey: RMXZRJYGJMSDQK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-[4-methoxy-3-(piperazin-1-yl)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide hydrochloride
• IUPAC Traditional name: 5-chloro-N-[4-methoxy-3-(piperazin-1-yl)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide hydrochloride
• Synonyms: 5-Chloro-N-(4-methoxy-3-piperazin-1-yl-phenyl)-3-methyl-2-benzo-thiophenesulfonamide hydrochloride; SB-271046A

Database IDs

• CAS Number: 209481-24-3
• MDL Number: MFCD10565914
• PubChem SID: 162248801
• PubChem CID: 6918455

CALCULATED PROPERTIES

• Acid pKa: 6.4322987
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.0125964
• LogD (pH = 7.4): 2.9310358
• Log P: 2.9765599
• Molar Refractivity: 116.8834 cm^3
• Polarizability: 46.847363 Å^3
• Polar Surface Area: 70.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: powder

Safety Information

• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H22ClN3O3S2 · HCl

DETAILS

Sigma Aldrich - S5326

Biochem/physiol Actions
The first potent and selective 5-HT6 antagonist. Training in cognitive tasks, as well as administration SB-271046, induces an increase in pERK1/2 and pCREB1 levels, while CREB2 levels are significantly reduced; cognition-enhancing properties of SB-271046 are attributed to the effect on pERK1/2, not pCREB1/2.1 SB-271046 reverses MK-801-induced, but not scopolamine-induced, learning impairments. However, with coadministration of galanthamine, both types of learning impairments were ameliorated.2