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293753-05-6

中文名稱 SR3335
英文名稱 SR3335
CAS 293753-05-6
分子式 C13H9F6NO3S2
分子量 405.336
MOL 文件 293753-05-6.mol
更新日期 2024/07/08 16:38:17
293753-05-6 結(jié)構(gòu)式 293753-05-6 結(jié)構(gòu)式

基本信息

中文別名
化合物SR3335
N-[4-[2,2,2-三氟-1-羥基-1-(三氟甲基)乙基]苯基]-2-噻吩磺酰胺
英文別名
ML-176
SR3335
SR3335
ML176
ML-176
SR-3335
ML-176
SR 3335
SR-3335
ML176
ML 176
SR3335
ML-176
SR 3335
SR-3335
ML176
ML 176
SR 3335 (This product is only available in Japan.)
N-[4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)phenyl]thiophene-2-sulfonamide
N-[4-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-2-thiophenesulfonamide
2-Thiophenesulfonamide, N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-
所屬類別
生物化工:激動劑抑制劑

物理化學(xué)性質(zhì)

儲存條件Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
溶解度insoluble in H2O; ≥87.4 mg/mL in EtOH; ≥88.8 mg/mL in DMSO
形態(tài)固體
顏色White to off-white
InChIInChI=1S/C13H9F6NO3S2/c14-12(15,16)11(21,13(17,18)19)8-3-5-9(6-4-8)20-25(22,23)10-2-1-7-24-10/h1-7,20-21H
InChIKeyLZWUNZRMANFRAO-UHFFFAOYSA-N
SMILESC1(S(NC2=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C2)(=O)=O)SC=CC=1

制備方法

方法1
2-噻吩磺酰氯

16629-19-9

2-(4-氨基苯)-1,1,1,3,3,3-六氟-2-丙醇

722-92-9

SR3335

293753-05-6

在氬氣保護(hù)下,將4-(1-羥基-1-三氟甲基-2,2,2-三氟乙基)苯胺(A)(1.5M THF溶液,128μL,0.193mmol)溶于丙酮(643μL)中。隨后,依次加入2,6-二甲基吡啶(29μL,0.251mmol)和2-噻吩磺酰氯(0.193mmol),反應(yīng)在室溫下進(jìn)行。將反應(yīng)混合物加熱至80℃,持續(xù)反應(yīng)1天。反應(yīng)完成后,冷卻至室溫,用乙酸乙酯(EtOAc)和飽和碳酸氫鈉(NaHCO3)溶液稀釋。水相用乙酸乙酯萃取兩次,合并有機(jī)相,經(jīng)無水硫酸鈉(Na2SO4)干燥,過濾并濃縮。粗產(chǎn)物通過硅膠柱色譜法純化,使用己烷/乙酸乙酯(7/3)作為洗脫劑,得到目標(biāo)產(chǎn)物N-[4-[2,2,2-三氟-1-羥基-1-(三氟甲基)乙基]苯基]-2-噻吩磺酰胺(SR3335),為白色粉末,產(chǎn)量48mg(收率62%)。該化合物的CAS號為2937-53-05-6,文獻(xiàn)已知并可商購。

參考文獻(xiàn):

[1] Patent: WO2011/115892, 2011, A1. Location in patent: Page/Page column 6; 45; 46

圖譜信息

SR3335價格(試劑級)
報價日期產(chǎn)品編號產(chǎn)品名稱CAS號包裝價格
2025/05/22HY-14413SR3335293753-05-61 mg386元
2025/05/22HY-14413SR3335
SR3335
293753-05-65mg850元
2025/05/22HY-14413SR3335
SR3335
293753-05-610mM * 1mLin DMSO935元

常見問題列表

生物活性
SR3335 (ML 176) 是選擇性的 RORα 反向激動劑,可直接結(jié)合 RORα,Ki為 220 nM。
靶點

Ki: 220 nM (RORα)

體外研究

SR3335 is a selective RORα partial inverse agonist. In a biochemical radioligand binding assay using [ 3 H]25-hydroxycholesterol as a label it is clear that unlabeled SR3335 dose-dependently competes for binding to the RORα LBD. The K i is calculated as 220 nM using the Cheng-Prusoff equation. In a cell-based chimeric receptor Gal4 DNA-binding domain-NR ligand binding domain cotransfection assay, SR3335 significantly inhibits the constitutive transactivation activity of RORα (IC 50 =480 nM)(partial inverse agonist activity), but has no effect on the activity of LXRα and RORγ.
SR3335 suppresses the expression of endogenous RORα target genes in HepG2 cells that are involved in hepatic gluconeogenesis including glucose-6-phosphatase (G6Pase) and phosphoenolpyruvate carboxykinase (PEPCK).
SR3335 also blocks IL-25 and IL-33-induced ILC2 proliferation and IL-13 production ex vivo.

體內(nèi)研究

SR3335 displays reasonable exposure following an i.p. injection into mice. The ability of SR3335 is assessed to suppress gluconeogenesis using a diet induced obesity (DIO) mouse model where the mice where treated with 15 mg/kg b.i.d., i.p. for 6-days followed by a pyruvate tolerance test. SR3335 treated mice displays lower plasma glucose levels following the pyruvate challenge consistent with suppression of gluconeogenesis. Importantly, mice treated with SR3335 displayed no difference in body weight or food intake after 7-days of treatment with SR3335.
SR3335 (15 mg/kg/day; ip for 7 days) reduces rhinovirus (RV)-induced lung ILC2s in immature mice (RV infection of 6-day-old BALB/c mice).

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