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2-(4-chlorophenyl)-8-ethoxyethyl-7-methylimidazo[1,2-a]pyrimidin-5(8H)-one

中文名称
——
中文别名
——
英文名称
2-(4-chlorophenyl)-8-ethoxyethyl-7-methylimidazo[1,2-a]pyrimidin-5(8H)-one
英文别名
2-(4-Chlorophenyl)-8-(2-ethoxyethyl)-7-methylimidazo[1,2-a]pyrimidin-5-one;2-(4-chlorophenyl)-8-(2-ethoxyethyl)-7-methylimidazo[1,2-a]pyrimidin-5-one
2-(4-chlorophenyl)-8-ethoxyethyl-7-methylimidazo[1,2-a]pyrimidin-5(8H)-one化学式
CAS
——
化学式
C17H18ClN3O2
mdl
——
分子量
331.802
InChiKey
AZUOXDNQPQTUAT-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):
    3.1
  • 重原子数:
    23
  • 可旋转键数:
    5
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    47.4
  • 氢给体数:
    0
  • 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

  • 作为产物:
    参考文献:
    名称:
    Identification of Potent In Vivo Autotaxin Inhibitors that Bind to Both Hydrophobic Pockets and Channels in the Catalytic Domain
    摘要:
    Autotaxin (ATX, also known as ENPP2) is a predominant lysophosphatidic acid (LPA)-producing enzyme in the body, and LPA regulates various physiological functions, such as angiogenesis and wound healing, as well as pathological functions, including proliferation, metastasis, and fibrosis, via specific LPA receptors. Therefore, the ATX-LPA axis is a promising therapeutic target for dozens of diseases, including cancers, pulmonary and liver fibroses, and neuropathic pain. Previous structural studies revealed that the catalytic domain of ATX has a hydrophobic pocket and a hydrophobic channel; these serve to recognize the substrate, lysophosphatidylcholine (LPC), and deliver generated LPA to LPA receptors on the plasma membrane. Most reported ATX inhibitors bind to either the hydrophobic pocket or the hydrophobic channel. Herein, we present a unique ATX inhibitor that binds mainly to the hydrophobic pocket and also partly to the hydrophobic channel, inhibiting ATX activity with high potency and selectivity in vitro and in vivo. Notably, our inhibitor can rescue the cardia bifida (two hearts) phenotype in ATX-overexpressing zebrafish embryos.
    DOI:
    10.1021/acs.jmedchem.9b01967
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文献信息

  • 8-SUBSTITUTED IMIDAZOPYRIMIDINONE DERIVATIVE HAVING AUTOTAXIN INHIBITORY ACTIVITY
    申请人:THE UNIVERSITY OF TOKYO
    公开号:US20160002247A1
    公开(公告)日:2016-01-07
    A compound of formula (I) wherein variables are as defined herein having an autotaxin inhibitory effect and a pharmaceutical composition comprising the same.
    具有自体脂肪酶抑制作用的化合物(I)的化学式,其中变量如本文所定义,并且包含该化合物的药物组合物。
  • Identification of Potent <i>In Vivo</i> Autotaxin Inhibitors that Bind to Both Hydrophobic Pockets and Channels in the Catalytic Domain
    作者:Mitsuyasu Kawaguchi、Takayoshi Okabe、Shinichi Okudaira、Kotaro Hama、Kuniyuki Kano、Hiroshi Nishimasu、Hidehiko Nakagawa、Ryuichiro Ishitani、Hirotatsu Kojima、Osamu Nureki、Junken Aoki、Tetsuo Nagano
    DOI:10.1021/acs.jmedchem.9b01967
    日期:2020.3.26
    Autotaxin (ATX, also known as ENPP2) is a predominant lysophosphatidic acid (LPA)-producing enzyme in the body, and LPA regulates various physiological functions, such as angiogenesis and wound healing, as well as pathological functions, including proliferation, metastasis, and fibrosis, via specific LPA receptors. Therefore, the ATX-LPA axis is a promising therapeutic target for dozens of diseases, including cancers, pulmonary and liver fibroses, and neuropathic pain. Previous structural studies revealed that the catalytic domain of ATX has a hydrophobic pocket and a hydrophobic channel; these serve to recognize the substrate, lysophosphatidylcholine (LPC), and deliver generated LPA to LPA receptors on the plasma membrane. Most reported ATX inhibitors bind to either the hydrophobic pocket or the hydrophobic channel. Herein, we present a unique ATX inhibitor that binds mainly to the hydrophobic pocket and also partly to the hydrophobic channel, inhibiting ATX activity with high potency and selectivity in vitro and in vivo. Notably, our inhibitor can rescue the cardia bifida (two hearts) phenotype in ATX-overexpressing zebrafish embryos.
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