3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide

• ChemBase编号: 154502
• 分子式: C17H16ClN3OS
• 平均质量: 345.84644
• 单一同位素质量: 345.07026083
• SMILES: Cc1cc(nc2c1c(c(s2)C(=O)NCc1ccc(cc1)Cl)N)C
• Canonical SMILES: Clc1ccc(cc1)CNC(=O)c1sc2c(c1N)c(C)cc(n2)C
• InChI: InChI=1S/C17H16ClN3OS/c1-9-7-10(2)21-17-13(9)14(19)15(23-17)16(22)20-8-11-3-5-12(18)6-4-11/h3-7H,8,19H2,1-2H3,(H,20,22)
• InChIKey: FPRULFHDSFKYBV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide
• IUPAC传统名: 3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide
• 别名: 2-Furoyl-Leu-Ile-Gly-Arg-Leu-Orn-NH2 trifluoroacetate salt; 2-Fly; 2-f-LIGRLO-NH2; 2-fAP; 2fLI; f-LIGRLO-NH2; 2-Furoyl-LIGRLO-amide trifluoroacetate salt

登记号

• CAS号: 729589-58-6(freebase)
• MDL号: MFCD03821022
• PubChem SID: 162248641
• PubChem CID: 714286

理论计算性质

• Acid pKa: 15.655625
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 4.00014
• LogD (pH = 7.4): 4.000199
• Log P: 4.0001993
• 摩尔折射率: 94.7035 cm^3
• 极化性: 35.73852 Å^3
• 极化表面积: 68.01 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: >2 mg/mL
• 外观: white powder

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C36H63N11O8 · xC2HF3O2

详细说明

Sigma Aldrich - F3681

Biochem/physiol Actions
2-Furoyl-LIGRLO-amide is a potent and selective protease-activated receptor 2 (PAR2) agonist. PAR-2 activation is associated with increases in cAMP and intracellular Ca(2+). Immunoblot analysis revealed increases in phosphorylation of epidermal growth factor (EGF) receptor (EGFR) tyrosine kinase, Src, Pyk2, cRaf, and ERK1/2 in response to PAR-2 activation. 2-Furoyl-LIGRLO-amide is nearly 100-fold more potent than SLIGRL-NH2 (Cat. No. S9317). 2-Furoyl-LIGRLO-amide caused both an endothelium-dependent relaxation and an endothelium-independent contraction. It produced delayed (6 hours later) facilitation of capsaicin-evoked visceral nociception, an effect being much more potent than SLIGRL-NH2. Such effects were mimicked by i.col. trypsin. 2-f-LIGRL-NH2, coadministered repeatedly with caerulein six times in total, abolished the caerulein-evoked abdominal hyperalgesia/allodynia in WT, but not PAR2-KO, mice. Repeated doses of 2-f-LIGRL-NH2 moderately attenuated the severity of caerulein-induced pancreatitis in WT animals. It induced a similar dose-dependent increase in Ca2 levels in the presence and absence of b-arrestins.