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

• ChemBase编号: 154877
• 分子式: C16H14N4O4S
• 平均质量: 358.37176
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-[(5-methoxy-1H-1,3-benzodiazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide
• IUPAC传统名: 2-[(5-methoxy-1H-1,3-benzodiazol-2-yl)sulfanyl]-N-(4-nitrophenyl)acetamide
• 别名: 2-[(6-methoxy-1H-benzimidazol-2-yl)thio]-N-(4-nitrophenyl)-acetamide; AG-09/1

登记号

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

理论计算性质

• Acid pKa: 10.721355
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 2.9004765
• LogD (pH = 7.4): 2.9543157
• Log P: 2.9552355
• 摩尔折射率: 95.4981 cm^3
• 极化性: 36.576836 Å^3
• 极化表面积: 112.83 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥30 mg/mL
• 外观: yellow to brown powder

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 41
• 安全公开号: 26-39
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H318
• GHS警示性声明: P280-P305 + P351 + P338
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.