885101-89-3
885101-89-3 結(jié)構(gòu)式
基本信息
4-[[(3-苯氧基苯基)甲基]氨基]苯丙酸
3-(4-((3-苯氧基芐基)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
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
應(yīng)用領(lǐng)域
制備方法
2393-17-1
39515-51-0
885101-89-3
以3-(4-氨基苯基)丙酸和間苯氧基苯甲醛為原料合成4-[[(3-苯氧苯基)甲基]氨基]苯基乙酸的一般步驟：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）。將混合物進(jìn)行超聲處理，隨后轉(zhuǎn)移至20 mL微波反應(yīng)瓶中。在微波反應(yīng)器中，于100℃下反應(yīng)10分鐘。反應(yīng)完成后，將溶液轉(zhuǎn)移至500 mL圓底燒瓶中，分批加入三乙酰氧基硼氫化鈉（7.8 g，36.9 mmol）。反應(yīng)混合物在室溫下攪拌1小時(shí)。向反應(yīng)混合物中加入水（100 mL），分離有機(jī)層。有機(jī)層依次用水（100 mL）洗滌兩次，并用無(wú)水硫酸鈉干燥。減壓濃縮除去溶劑，粗產(chǎn)物通過(guò)硅膠柱色譜純化，洗脫劑為體積比1:1的己烷/乙酸乙酯混合溶劑，并加入微量乙酸。最終得到純的3-(4-((3-苯氧基芐基)氨基)苯基)丙酸（5.5 g，收率86%），為低熔點(diǎn)固體。產(chǎn)物經(jīng)1H NMR（CDCl3）和質(zhì)譜（MS）確認(rèn)：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+)。
參考文獻(xiàn)：
[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
| 報(bào)價(jià)日期 | 產(chǎn)品編號(hào) | 產(chǎn)品名稱(chēng) | CAS號(hào) | 包裝 | 價(jià)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 |
常見(jiàn)問(wèn)題列表
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.