2-[(5-methoxy-1H-1,3-benzodiazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide

• ChemBase ID: 154877
• Molecular Formular: C16H14N4O4S
• Molecular Mass: 358.37176
• Monoisotopic Mass: 358.07357595
• SMILES: COc1ccc2c(c1)nc([nH]2)SCC(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: COc1ccc2c(c1)nc([nH]2)SCC(=O)Nc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C16H14N4O4S/c1-24-12-6-7-13-14(8-12)19-16(18-13)25-9-15(21)17-10-2-4-11(5-3-10)20(22)23/h2-8H,9H2,1H3,(H,17,21)(H,18,19)
• InChIKey: LYQDSNOFTIZWAX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5-methoxy-1H-1,3-benzodiazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide
• IUPAC Traditional name: 2-[(5-methoxy-1H-1,3-benzodiazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide
• Synonyms: 2-[(6-methoxy-1H-benzimidazol-2-yl)thio]-N-(4-nitrophenyl)-acetamide; AG-09/1

Database IDs

• CAS Number: 356776-32-4
• MDL Number: MFCD02321063
• PubChem SID: 162249015
• PubChem CID: 3901842

CALCULATED PROPERTIES

• Acid pKa: 10.721355
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.9004765
• LogD (pH = 7.4): 2.9543157
• Log P: 2.9552355
• Molar Refractivity: 95.4981 cm^3
• Polarizability: 36.576836 Å^3
• Polar Surface Area: 112.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: yellow to brown powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H14N4O4S

DETAILS

Sigma Aldrich - A9486

Biochem/physiol Actions
AG-09/1 is a selective formyl peptide receptor 1 (FPR1) agonist; it activates chemotaxis in human neutrophils. Formyl peptide recetors (FPRs) are GPCRs mainly expressed in phagocytic leukocytes but with lower expression in many other cell types. Formyl peptides, act as Alarmins and are released from bacteria and damaged mitochondria, serving as chemoattractants for phagocyte recruitment to sites of inflammation, resulting in immune response. Because the endogenous ligands for FPRs are peptides and arachadonic acid metabolites, there are few small molecule tools for these receptors. A recent HTS of commercially available libraries yielded several FPR-1 selective agonists, of which AG-091 was the most potent. AG-091 induced intracellular calcium flux in FPR-1- but not FPR-2-expressing cells. It also caused chemotaxis and intracellular calcium flux in human leukocytes. AG-091 is a valuable tool for studying FPR1 function in immune and other disease states.