反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
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- CAS號:
- 193551-21-2
- 英文名:
- SB 239063
- 英文別名:
- CS-402;SB 239063;SB-239063; SB239063;SB 239063 - Bio-X ?;SB 239063, 10 mM in DMSO;rans-4-[4-(4-Fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)-1H-imidazol-1-yl]cyclohexano;TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(FLUOROPHENYL)-5-(2-METHOXYPYRIMIDIN-4-YL) IMIDAZOLE;TRANS-4-[4-(4-FLUOROPHENYL)-5-(2-METHOXY-4-PYRIMIDINYL)-1H-IMIDAZOL-1-YL]CYCLOHEXANOL;TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(4-FLUOROPHENYL)-5-(2-METHOXYPYRIMIDIN-4-YL) IMIDAZOLE;TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(4-FLUOROPHENYL)-5-(2-METHOXYPYRIDIMIDIN-4-YL)IMIDAZOLE
- 中文名:
- 反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
- 中文別名:
- 化合物L(fēng)-779450;SB 239063試劑;SB 239063試劑;化合物SB239063,10 MM DMSO 溶液;SB 239063 (SB-239063;SB239063);反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑;反-4-[4-(4-氟苯基)-5-(2-甲氧基-4-嘧啶基)-1H-咪唑-1-基]環(huán)己醇;(1R,4R)-REL-4-(4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)-1H-咪唑-1-基)環(huán)己醇
- CBNumber:
- CB6100319
- 分子式:
- C20H21FN4O2
- 分子量:
- 368.4
- MOL File:
- 193551-21-2.mol
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反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑化學(xué)性質(zhì)
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熔點(diǎn):
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206-207.2 °C
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儲存條件:
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2-8°C
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溶解度:
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DMSO: 11 mg/mL
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形態(tài):
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White solid
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顏色:
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white
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InChI:
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InChI=1S/C20H21FN4O2/c1-27-20-22-11-10-17(24-20)19-18(13-2-4-14(21)5-3-13)23-12-25(19)15-6-8-16(26)9-7-15/h2-5,10-12,15-16,26H,6-9H2,1H3/t15-,16-
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InChIKey:
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ZQUSFAUAYSEREK-WKILWMFISA-N
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SMILES:
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[C@@H]1(O)CC[C@@H](N2C=NC(C3=CC=C(F)C=C3)=C2C2C=CN=C(OC)N=2)CC1
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反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑性質(zhì)、用途與生產(chǎn)工藝
SB239063是一種有效的選擇性p38 MAPKα/β抑制劑，IC50為44 nM，對γ- 和 δ-激酶亞型沒有活性。
| Target | Value |
p38α
(Cell-free assay)
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44 nM
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p38β
(Cell-free assay)
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44 nM
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SB 239063 (0.1–10 μM ; 29 hours, 47 hours) increases apoptosis of eosinophils in a dose-related in the presence of 10 pM IL-5 at every time point from 21 hours onwards.
SB 239063 potently inhibits IL-1 and TNF- a production in LPS-stimulated human peripheral blood monocytes with IC
50
values of 120 nM and 350 nM, respectively.
Apoptosis Analysis
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Cell Line:
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Eosinophils (guinea pig BALs)
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Concentration:
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0.1μM, 1μM, 10μM
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Incubation Time:
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29 hours, 47 hours
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Result:
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Increased apoptosis of eosinophils in a dose-related in the presence of 10 pM IL-5 at every time point from 21 hours onwards.
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SB 239063 (12 mg/kg; p.o.; 1 hour before and 4 hours after OA challenge; b.i.d. for 3 days) significantly inhibits the resultant antigen-induced airway eosinophilia.
SB 239063 (12 mg/kg; p.o.) almost abolishes ovalbumin (OA)-induced airway eosinophilia (~ 93% inhibition) by inhalation.
SB 239063 is a potent inhibitor of LPS-induced TNF-alpha production in the mouse peritoneal cavity with an EC
50
of 5.8 mg/kg (2.8–10.3; 95% CL).
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Animal Model:
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Male BALB/c mice (18–20 g)
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Dosage:
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12 mg/kg
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Administration:
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Oral administration; 1 h before and 4 h after OA challenge; bis in die for 3 days
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Result:
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Significantly inhibited the resultant antigen-induced airway eosinophilia.
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生產(chǎn)方法
以化合物（CAS: 193551-20-1）為起始原料，合成(1r,4r)-rel-4-(4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)-1H-咪唑-1-基)環(huán)己醇的一般步驟如下：
實(shí)施例2：反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑的合成
向?qū)嵤├?（j）中制備的化合物溶液（0.099 g，溶解于MeOH/THF（1 mL，體積比1:1）中，對應(yīng)0.27 mmol）加入NaBH4溶液（1 mL，1 M溶液。該NaBH4溶液通過將0.10 g NaBH4、MeOH（2.5 mL）和25% NaOMe的MeOH溶液（0.2 mL）混合制備而成）。反應(yīng)混合物攪拌10分鐘后，用飽和Na2CO3溶液淬滅反應(yīng)，隨后蒸發(fā)除去溶劑。殘余物通過從MeOH/H2O混合溶劑中重結(jié)晶純化，得到目標(biāo)產(chǎn)物(1r,4r)-rel-4-(4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)-1H-咪唑-1-基)環(huán)己醇，為白色針狀晶體（0.063 g，收率63%）。產(chǎn)物的熔點(diǎn)為188-190℃。
參考文獻(xiàn)：
[1] Patent: US6329526, 2001, B1
反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
上下游產(chǎn)品信息
上游原料
下游產(chǎn)品
| 更新日期 | 產(chǎn)品編號 | 產(chǎn)品名稱 | CAS編號 | 包裝 | 價(jià)格 |
|---|
| 2026/07/06 | S7741 | 反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
SB239063 | 193551-21-2 | 5mg | 1115.26元 |
| 2026/07/06 | S7741 | 反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
SB239063 | 193551-21-2 | 10mM (1mL in DMSO) | 1285.83元 |
反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
生產(chǎn)廠家
反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑 圖譜信息:
193551-21-2, 反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑 相關(guān)搜索:
環(huán)己甲酰胺 2-(2-亞氨基-4,5,6,7-四氫苯并噻唑-3-基)-1-P-甲苯基乙酮?dú)滗逅猁} N/A 4-[4-(4-氟苯基)-2-(4-硝基苯基)-1H-咪唑-5-基]吡啶 CP31398 4-(4-氟苯基)-2-(4-羥基苯基)-5-(4-吡啶基)-1H-咪唑 5,6,7,8-四氫-2-(4-甲基苯基)-咪唑并[2,1-B]苯并噻唑 1H-吲哚-5-甲酰胺 環(huán)己基乙烯基醚 1-(2-甲基苯并[D]噁唑-6-基)-3-(1,5-萘啶-4-基)脲 SB204741 4-[4-(4-氟苯基)-1-(4-哌啶基)-1H-咪唑-5-基]-2-甲氧基嘧啶 SB225002 (S)-METHYL-2-NAPHTHOYLAMINO-3-(4-NITROPHENYL)PROPIONATE SB297006 Benzamide,N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitro-,hydrochloride(1:1) 化合物SB-265610
- Protein Kinase Inhibitors and Activators
- Heterocycles
- Aromatics
- 抑制劑
- 生化試劑
- Cell Signaling and Neuroscience
- Cell Biology
- BioChemical
- Serine/Threonine Kinase Inhibitors
- Mitogen-Activated Protein Kinase (MAPK)
- Kinase/Phosphatase Biology
- C20H21N4O2F
- SB 239063試劑
- SB 239063 (SB-239063;SB239063)
- SB 239063試劑
- 化合物SB239063,10 MM DMSO 溶液
- 化合物L(fēng)-779450
- (1R,4R)-REL-4-(4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)-1H-咪唑-1-基)環(huán)己醇
- 反-4-[4-(4-氟苯基)-5-(2-甲氧基-4-嘧啶基)-1H-咪唑-1-基]環(huán)己醇
- 反式-1-(4-羥基環(huán)己基)-4-(4-氟苯基)-5-(2-甲氧基嘧啶-4-基)咪唑
- 193551-21-2
- SB 239063 - Bio-X ?
- SB 239063, 10 mM in DMSO
- Rel-(1r,4r)-4-(4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)-1H-imidazol-1-yl)cyclohexan-1-ol
- rans-4-[4-(4-Fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)-1H-imidazol-1-yl]cyclohexano
- SB-239063; SB239063
- CS-402
- Cyclohexanol, 4-[4-(4-fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)-1H-imidazol-1-yl]-, trans-
- TRANS-4-[4-(4-FLUOROPHENYL)-5-(2-METHOXY-4-PYRIMIDINYL)-1H-IMIDAZOL-1-YL]CYCLOHEXANOL
- TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(FLUOROPHENYL)-5-(2-METHOXYPYRIMIDIN-4-YL) IMIDAZOLE
- TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(4-FLUOROPHENYL)-5-(2-METHOXYPYRIMIDIN-4-YL) IMIDAZOLE
- TRANS-1-(4-HYDROXYCYCLOHEXYL)-4-(4-FLUOROPHENYL)-5-(2-METHOXYPYRIDIMIDIN-4-YL)IMIDAZOLE
- SB 239063