4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide

• ChemBase ID: 153982
• Molecular Formular: C18H10Br2ClN3OS
• Molecular Mass: 511.6175
• Monoisotopic Mass: 508.85998464
• SMILES: c1cc(sc1)c1c(n2cc(cc(c2n1)Br)Br)NC(=O)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)C(=O)Nc1c(nc2n1cc(Br)cc2Br)c1cccs1
• InChI: InChI=1S/C18H10Br2ClN3OS/c19-11-8-13(20)16-22-15(14-2-1-7-26-14)17(24(16)9-11)23-18(25)10-3-5-12(21)6-4-10/h1-9H,(H,23,25)
• InChIKey: MEWSBNIVOLYKGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide
• IUPAC Traditional name: DS-1 (drug)
• Synonyms: 4-Chloro-N-[6,8-dibromo-2-(2-thienyl)imidazo[1,2-a]pyridine-3-yl]benzamide; DS1

Database IDs

• CAS Number: 372497-52-4
• MDL Number: MFCD01943217
• PubChem SID: 162248121
• PubChem CID: 979735

CALCULATED PROPERTIES

• Acid pKa: 11.073646
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.8862524
• LogD (pH = 7.4): 5.892313
• Log P: 5.892499
• Molar Refractivity: 112.4277 cm^3
• Polarizability: 43.07775 Å^3
• Polar Surface Area: 46.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white to tan powder

Safety Information

• Storage Condition: desiccated
• 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): C18H10Br2ClN3OS

DETAILS

Sigma Aldrich - D0446

Biochem/physiol Actions
δ-GABAA receptors are emerging as an important pharmacological target. DS1 potently (low nM) enhances GABA-evoked currents mediated by α4β3δ receptors. It had little effect on GABA responses mediated by α4β3γ2 receptors. At similar concentrations DS1 directly activates this receptor and is the most potent known agonist of α4β3δ receptors. This compound has an opportunity to be become an agonist golden stardard for δ-GABAA receptors.
DS1 potently (low nM) enhances GABA-evoked currents mediated by GABAA α4β3δ receptor subtype. At similar concentrations, it acts as a direct agonist at this receptor and is the most potent agonist known. It has little effect on GABA responses mediated by α4β3γ2 receptors.