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Substituted 6-aminoquinoline-3-carbonitrile, 31 | 915366-73-3

中文名称
——
中文别名
——
英文名称
Substituted 6-aminoquinoline-3-carbonitrile, 31
英文别名
8-chloro-4-(3-chloro-4-fluoroanilino)-6-[[1-[2-(1-ethylpiperidin-4-yl)ethyl]triazol-4-yl]methylamino]quinoline-3-carbonitrile
Substituted 6-aminoquinoline-3-carbonitrile, 31化学式
CAS
915366-73-3
化学式
C28H29Cl2FN8
mdl
——
分子量
567.496
InChiKey
CWDAVPSQFFXORE-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):
    6.1
  • 重原子数:
    39
  • 可旋转键数:
    9
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    94.7
  • 氢给体数:
    2
  • 氢受体数:
    8

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:
    描述:
    6-氨基-8-氯-4-[(3-氯-4-氟苯基)氨基]-3-喹啉甲腈 、 1-(2-(1-ethylpiperidin-4-yl)ethyl)-1H-1,2,3-triazole-4-carbaldehyde 在 三乙酰氧基硼氢化钠 作用下, 以 1,2-二氯乙烷 为溶剂, 反应 4.0h, 生成 Substituted 6-aminoquinoline-3-carbonitrile, 31
    参考文献:
    名称:
    Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-α production in human whole blood
    摘要:
    Tpl2 (cot/MAP3K8) is an upstream kinase of MEK in the ERK pathway. It plays an important role in Tumor Necrosis Factor-alpha (TNF-alpha) production and signaling. We have discovered that 8-halo-4-(3-chloro-4-fluorophenylamino)-6-[(1H-[ 1,2,3]triazol-4-ylmethyl)-amino]-quinoline-3-carbonitriles (4) are potent inhibitors of this enzyme. In order to improve the inhibition of TNF-alpha production in LPS-stimulated human blood, a series of analogs with a variety of substitutions around the triazole moiety were studied. We found that a cyclic amine group appended to the triazole ring could considerably enhance potency, aqueous solubility, and cell membrane permeability. Optimization of these cyclic amine groups led to the identification of 8-chloro-4-(3-chloro-4-fluorophenylamino)-6-((1-(1-ethylpiperidin-4-yl)-1H-1,2,3-triazol- 4-yl) methylamino)quinoline-3-carbonitrile (34). In a LPS-stimulated rat inflammation model, compound 34 showed good efficacy in inhibiting TNF-alpha production. (C) 2009 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2009.05.009
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文献信息

  • Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-α production in human whole blood
    作者:Junjun Wu、Neal Green、Rajeev Hotchandani、Yonghan Hu、Jeffrey Condon、Adrian Huang、Neelu Kaila、Huan-Qiu Li、Satenig Guler、Wei Li、Steve Y. Tam、Qin Wang、Jeffrey Pelker、Suzana Marusic、Sang Hsu、J. Perry Hall、Jean-Baptiste Telliez、Junqing Cui、Lih-Ling Lin
    DOI:10.1016/j.bmcl.2009.05.009
    日期:2009.7
    Tpl2 (cot/MAP3K8) is an upstream kinase of MEK in the ERK pathway. It plays an important role in Tumor Necrosis Factor-alpha (TNF-alpha) production and signaling. We have discovered that 8-halo-4-(3-chloro-4-fluorophenylamino)-6-[(1H-[ 1,2,3]triazol-4-ylmethyl)-amino]-quinoline-3-carbonitriles (4) are potent inhibitors of this enzyme. In order to improve the inhibition of TNF-alpha production in LPS-stimulated human blood, a series of analogs with a variety of substitutions around the triazole moiety were studied. We found that a cyclic amine group appended to the triazole ring could considerably enhance potency, aqueous solubility, and cell membrane permeability. Optimization of these cyclic amine groups led to the identification of 8-chloro-4-(3-chloro-4-fluorophenylamino)-6-((1-(1-ethylpiperidin-4-yl)-1H-1,2,3-triazol- 4-yl) methylamino)quinoline-3-carbonitrile (34). In a LPS-stimulated rat inflammation model, compound 34 showed good efficacy in inhibiting TNF-alpha production. (C) 2009 Elsevier Ltd. All rights reserved.
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