885101-89-3
885101-89-3 结构式
基本信息
4-[[(3-苯氧基苯基)甲基]氨基]苯丙酸
3-(4-((3-苯氧基苄基)氨基)苯基)丙酸
CS-618
GPR40 Agonist
GW9508, >=99%
GW9508 USP/EP/BP
885101-89-3(GW9508)
GW-9508
GW9508
GW 9508
4-(3-Phenoxybenzylamino)phenylpropionic acid
GPR40 Agonist - CAS 885101-89-3 - Calbiochem
3-(4-((3-Phenoxybenzyl)aMino)phenyl)propanoic acid
物理化学性质
应用领域
制备方法
2393-17-1
39515-51-0
885101-89-3
以3-(4-氨基苯基)丙酸和间苯氧基苯甲醛为原料合成4-[[(3-苯氧苯基)甲基]氨基]苯基乙酸的一般步骤：向3-苯氧基苯甲醛（3.2 mL，18.5 mmol）的二氯乙烷（60 mL）溶液中加入3-(4-氨基苯基)丙酸（3.0 g，18.5 mmol）。将混合物进行超声处理，随后转移至20 mL微波反应瓶中。在微波反应器中，于100℃下反应10分钟。反应完成后，将溶液转移至500 mL圆底烧瓶中，分批加入三乙酰氧基硼氢化钠（7.8 g，36.9 mmol）。反应混合物在室温下搅拌1小时。向反应混合物中加入水（100 mL），分离有机层。有机层依次用水（100 mL）洗涤两次，并用无水硫酸钠干燥。减压浓缩除去溶剂，粗产物通过硅胶柱色谱纯化，洗脱剂为体积比1:1的己烷/乙酸乙酯混合溶剂，并加入微量乙酸。最终得到纯的3-(4-((3-苯氧基苄基)氨基)苯基)丙酸（5.5 g，收率86%），为低熔点固体。产物经1H NMR（CDCl3）和质谱（MS）确认：1H NMR (CDCl3) δ 2.40 (t, 2H), 2.63 (t, 2H), 4.21 (s, 2H), 6.09 (bs, 1H), 6.44-6.47 (m, 2H), 6.81-6.83 (m, 1H), 6.87-6.89 (m, 2H), 6.94-6.97 (m, 2H), 7.07 (bs, 1H), 7.11-7.18 (m, 2H), 7.29-7.33 (m, 1H), 7.35-7.38 (m, 2H), 12.09 (bs, 1H); MS m/z = 348 (M + H+)。
参考文献：
[1] Patent: WO2012/97427, 2012, A1. Location in patent: Page/Page column 41-42
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 2981 - 2989
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1840 - 1845
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2025/05/22 | HY-15589 | GW9508 | 885101-89-3 | 5 mg | 312元 |
| 2025/05/22 | HY-15589 | 885101-89-3(GW9508) GW9508 | 885101-89-3 | 10mg | 500元 |
| 2025/05/22 | HY-15589 | 885101-89-3(GW9508) GW9508 | 885101-89-3 | 10mM * 1mLin DMSO | 550元 |
常见问题列表
pEC50: 7.32 (GPR40) and 5.46 (GPR120)
GW9508 stimulates intracellular Ca
2+
mobilization in HEK-293 cells expressing GPR40 (pEC
50
of 7.32) or GPR120 (pEC
50
of 5.46), but not in the parent HEK-293 cell line.
GW9508 produces a concentration-dependent increase (pEC
50
of 6.14) in glucose-stimulated insulin secretion at high glucose levels (25 mM). This resulted in a 1.52-fold increase in insulin secretion with 20 μM GW9508 in the presence of 25 mM glucose, compared with 25 mM glucose alone. The ability of GW9508 (10 μM) to enhance insulin secretion from MIN6 cells is significantly enhanced as glucose concentrations are increased.
GW9508 inhibits CCL17 and CCL5 expression in a pertussis toxin-sensitive manner. The inhibitory effect by GW9508 is abrogated by depletion of GPR40 with RNA interference. GW9508 further suppresses expression of IL-11, IL-24, and IL-33 induced in HaCaT cells by TNF-α and IFN-γ. GW9508 also inhibits CCL5 and CXCL10 production by normal human epidermal keratinocytes.
Administration of GW9508 200 (μM) topically to the skin suppresses ear swelling in a repeated hapten application model (BALB/c and C57BL/6 mice) and contact hypersensitivity with downregulation of CCL5 and CXCL10, respectively.