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5-bromo-6-(difluoromethoxy)-1H-indazole | 1613504-79-2

中文名称
——
中文别名
——
英文名称
5-bromo-6-(difluoromethoxy)-1H-indazole
英文别名
——
5-bromo-6-(difluoromethoxy)-1H-indazole化学式
CAS
1613504-79-2
化学式
C8H5BrF2N2O
mdl
——
分子量
263.041
InChiKey
GNNHRPDTGPUSRL-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:
    355.3±37.0 °C(Predicted)
  • 密度:
    1.794±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.2
  • 重原子数:
    14
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.12
  • 拓扑面积:
    37.9
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    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:
    描述:
    5-bromo-6-(difluoromethoxy)-1H-indazole四(三苯基膦)钯caesium carbonate对甲苯磺酸 作用下, 以 1,4-二氧六环氯仿 为溶剂, 生成 C20H17F5N2O2
    参考文献:
    名称:
    Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists
    摘要:
    A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.
    DOI:
    10.1021/jm401986p
  • 作为产物:
    参考文献:
    名称:
    Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists
    摘要:
    A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.
    DOI:
    10.1021/jm401986p
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文献信息

  • [EN] PYRAZOLOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS PYRAZOLOPYRIMIDINE ET LEURS PROCÉDÉS D'UTILISATION
    申请人:HOFFMANN LA ROCHE
    公开号:WO2018122212A1
    公开(公告)日:2018-07-05
    Compounds of Formula (IA), or a pharmaceutically acceptable salt thereof, and methods of use as Janus kinase inhibitors are described herein.
    化合物的结构式(IA),或其药用可接受的盐,以及作为Janus激酶抑制剂的使用方法在此处描述。
  • [EN] HTT MODULATORS FOR TREATING HUNTINGTON'S DISEASE<br/>[FR] MODULATEURS HTT POUR LE TRAITEMENT DE LA MALADIE DE HUNTINGTON
    申请人:CHDI FOUNDATION INC
    公开号:WO2021231571A1
    公开(公告)日:2021-11-18
    Provided herein are certain compounds useful as HTT modulators. Such compound are useful in the treatment of Huntington's disease.
    以下提供了一些作为HTT调节剂有用的化合物。这些化合物在亨廷顿病的治疗中很有用。
  • Pyrazolopyrimidine compounds and methods of use thereof
    申请人:Genentech, Inc.
    公开号:US11155557B2
    公开(公告)日:2021-10-26
    Compounds of Formula (IA), or a pharmaceutically acceptable salt thereof, and methods of use as Janus kinase inhibitors are described herein.
    本文描述了式(IA)化合物或其药学上可接受的盐,以及作为 Janus 激酶抑制剂的使用方法。
  • Discovery of a class of highly potent Janus Kinase 1/2 (JAK1/2) inhibitors demonstrating effective cell-based blockade of IL-13 signaling
    作者:Mark Zak、Emily J. Hanan、Patrick Lupardus、David G. Brown、Colin Robinson、Michael Siu、Joseph P. Lyssikatos、F. Anthony Romero、Guiling Zhao、Terry Kellar、Rohan Mendonca、Nicholas C. Ray、Simon C. Goodacre、Peter H. Crackett、Neville McLean、Christopher A. Hurley、Po-wai Yuen、Yun-Xing Cheng、Xiongcai Liu、Marya Liimatta、Pawan Bir Kohli、Jim Nonomiya、Gary Salmon、Gerry Buckley、Julia Lloyd、Paul Gibbons、Nico Ghilardi、Jane R. Kenny、Adam Johnson
    DOI:10.1016/j.bmcl.2019.04.008
    日期:2019.6
    Disruption of interleukin-13 (IL-13) signaling with large molecule antibody therapies has shown promise in diseases of allergic inflammation. Given that IL-13 recruits several members of the Janus Kinase family (JAK1, JAK2, and TYK2) to its receptor complex, JAK inhibition may offer an alternate small molecule approach to disrupting IL-13 signaling. Herein we demonstrate that JAK1 is likely the isoform most important to IL-13 signaling. Structure-based design was then used to improve the JAK1 potency of a series of previously reported JAK2 inhibitors. The ability to impede IL-13 signaling was thereby significantly improved, with the best compounds exhibiting single digit nM IC50's in cell-based assays dependent upon IL-13 signaling. Appropriate substitution was further found to influence inhibition of a key off-target, LRRK2. Finally, the most potent compounds were found to be metabolically labile, which makes them ideal scaffolds for further development as topical agents for IL-13 mediated diseases of the lungs and skin (for example asthma and atopic dermatitis, respectively).
  • PYRAZOLOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF
    申请人:F. Hoffmann-La Roche AG
    公开号:EP3562809B1
    公开(公告)日:2021-06-09
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