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4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenol | 1251931-20-0

中文名称
——
中文别名
——
英文名称
4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenol
英文别名
4-[4,5-Dibromo-1-(methoxymethyl)imidazol-2-yl]phenol
4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenol化学式
CAS
1251931-20-0
化学式
C11H10Br2N2O2
mdl
——
分子量
362.021
InChiKey
LCSMGRCLTGHNIL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    488.7±55.0 °C(Predicted)
  • 密度:
    1.84±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    17
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.18
  • 拓扑面积:
    47.3
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents
    摘要:
    The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of human cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in human melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-{2-[4-(2-dimethylamino-ethoxy) phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl} benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol (1i) with BRAF IC50 = 190 nM and with cellular GI(50) = 2100 nM, and 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol (1q) with IC50 = 9 nM and GI(50) = 220 nM. (C) 2013 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2012.12.035
  • 作为产物:
    描述:
    4-羟基苯硼酸2,4,5-三溴-1-甲氧基甲基-1H-咪唑四(三苯基膦)钯potassium carbonate 作用下, 以 甲醇甲苯 为溶剂, 以39%的产率得到4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenol
    参考文献:
    名称:
    Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds
    摘要:
    V-RAF murine sarcoma viral oncogene homolog B1 (BRAF) is a serine/threonine-specific protein kinase that is mutated with high frequency in cutaneous melanoma, and many other cancers. Inhibition of mutant BRAF is an attractive therapeutic approach for the treatment of melanoma. A triarylimidazole BRAF inhibitor bearing a phenylpyrazole group (dimethyl-[2-(4-{5-[4-(1H-pyrazol-3-yl)-phenyl]-4-pyridin- 4-yl-1H-imidazol-2-yl}-phenoxy)-ethyl]-amine, 1a) was identified as an active BRAF inhibitor. Based on this starting point, we synthesized a series of analogues leading to the discovery of 6-{2-[4-(4-methylpiperazin- 1-yl)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-2,4-dihydro-indeno[1,2-c]pyrazole (1j), with nanomolar activity in three assays: inhibition of purified mutant BRAF activity in vitro; inhibition of oncogenic BRAF-driven extracellular regulated kinase (ERK) activation in BRAF mutant melanoma cell lines; and inhibition of proliferation in these cells. (C) 2010 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2010.06.031
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