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3-bromo-5-chloro-6-phenylpyrazolo[1,5-a]pyrimidin-7-amine | 934297-59-3

中文名称
——
中文别名
——
英文名称
3-bromo-5-chloro-6-phenylpyrazolo[1,5-a]pyrimidin-7-amine
英文别名
——
3-bromo-5-chloro-6-phenylpyrazolo[1,5-a]pyrimidin-7-amine化学式
CAS
934297-59-3
化学式
C12H8BrClN4
mdl
——
分子量
323.579
InChiKey
PEWIHHKGXFKVTP-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

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    18
  • 可旋转键数:
    1
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    56.2
  • 氢给体数:
    1
  • 氢受体数:
    3

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:
    3-bromo-5-chloro-6-phenylpyrazolo[1,5-a]pyrimidin-7-amine1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium hydride 、 caesium carbonate 作用下, 以 四氢呋喃1,4-二氧六环 、 mineral oil 为溶剂, 反应 17.67h, 生成 tert-butyl 4-(7-amino-5-((1,2,2,6,6-pentamethylpiperidin-4-yl)amino)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)benzoate
    参考文献:
    名称:
    Efficacy and Tolerability of Pyrazolo[1,5-a]pyrimidine RET Kinase Inhibitors for the Treatment of Lung Adenocarcinoma
    摘要:
    RET (REarranged during Transfection) kinase gain-of-function aberrancies have been identified as potential oncogenic drivers in lung adenocarcinoma, along with several other cancer types, prompting the discovery and assessment of selective inhibitors. Internal mining and analysis of relevant kinase data informed the decision to investigate a pyrazolo[1,5-a]pyrimidine scaffold, where subsequent optimization led to the identification of compound WF-47-JS03 (1), a potent RET kinase inhibitor with >500-fold selectivity against KDR (Kinase insert Domain Receptor) in cellular assays. In subsequent mouse in vivo studies, compound 1 demonstrated effective brain penetration and was found to induce strong regression of RET-driven tumor xenografts at a well-tolerated dose (10 mg/kg, po, qd). Higher doses of 1, however, were poorly tolerated in mice, similar to other pyrazolo[1,5-a]pyrimidine compounds at or near the efficacious dose, and indicative of the narrow therapeutic windows seen with this scaffold.
    DOI:
    10.1021/acsmedchemlett.0c00015
  • 作为产物:
    参考文献:
    名称:
    Efficacy and Tolerability of Pyrazolo[1,5-a]pyrimidine RET Kinase Inhibitors for the Treatment of Lung Adenocarcinoma
    摘要:
    RET (REarranged during Transfection) kinase gain-of-function aberrancies have been identified as potential oncogenic drivers in lung adenocarcinoma, along with several other cancer types, prompting the discovery and assessment of selective inhibitors. Internal mining and analysis of relevant kinase data informed the decision to investigate a pyrazolo[1,5-a]pyrimidine scaffold, where subsequent optimization led to the identification of compound WF-47-JS03 (1), a potent RET kinase inhibitor with >500-fold selectivity against KDR (Kinase insert Domain Receptor) in cellular assays. In subsequent mouse in vivo studies, compound 1 demonstrated effective brain penetration and was found to induce strong regression of RET-driven tumor xenografts at a well-tolerated dose (10 mg/kg, po, qd). Higher doses of 1, however, were poorly tolerated in mice, similar to other pyrazolo[1,5-a]pyrimidine compounds at or near the efficacious dose, and indicative of the narrow therapeutic windows seen with this scaffold.
    DOI:
    10.1021/acsmedchemlett.0c00015
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文献信息

  • Methods for inhibiting protein kinases
    申请人:Guzi J. Timothy
    公开号:US20070082900A1
    公开(公告)日:2007-04-12
    The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim kinases, and tyrosine kinase using pyrazolo[1,5-a]pyrimidine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.
    本发明提供了使用吡唑并[1,5-a]嘧啶化合物抑制选自AKT、检查点激酶、极光激酶、Pim激酶和酪氨酸激酶的蛋白激酶的方法,以及使用这些化合物治疗、预防、抑制或改善与蛋白激酶相关的一种或多种疾病的方法。
  • Pyrazolopyrimidines as protein kinase inhibitors
    申请人:Paruch Kamil
    公开号:US20070083044A1
    公开(公告)日:2007-04-12
    In its many embodiments, the present invention provides a novel class of amino-substituted pyrazolo[1,5-a]pyrimidine compounds as inhibitors of protein and/or checkpoint kinases, methods of preparing such compounds, pharmaceutical compositions including one or more such compounds, methods of preparing pharmaceutical formulations including one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the protein or checkpoint kinases using such compounds or pharmaceutical compositions.
    在本发明的多种实施方式中,提供了一类新颖的氨基取代的吡唑并[1,5-a]嘧啶化合物,作为蛋白质和/或检查点激酶的抑制剂,制备此类化合物的方法,包含一种或多种此类化合物的药物组合物,制备包含一种或多种此类化合物的药物制剂的方法,以及使用此类化合物或药物组合物治疗、预防、抑制或缓解与蛋白质或检查点激酶相关的一种或多种疾病的方法。
  • USE OF PYRAZOLO [1,5-A] PYRIMIDINE DERIVATIVES FOR INHIBITING KINASES METHODS FOR INHIBITING PROTEIN KINASES
    申请人:Merck Sharp & Dohme Corp.
    公开号:EP1942900B1
    公开(公告)日:2015-06-03
  • METHODS FOR INHIBITING PROTEIN KINASES
    申请人:Guzi Timothy J.
    公开号:US20100125068A1
    公开(公告)日:2010-05-20
    The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim kinases, and tyrosine kinase using pyrazolo[1,5-a]pyrimidine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.
  • US7776865B2
    申请人:——
    公开号:US7776865B2
    公开(公告)日:2010-08-17
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