3-(6-ethoxynaphthalen-2-yl)-1-(1-(methylsulfonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine | 1363386-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(6-ethoxynaphthalen-2-yl)-1-(1-(methylsulfonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• 英文别名: 3-(6-Ethoxy-2-naphthyl)-1-(1-methylsulfonyl-4-piperidyl)pyrazolo[3,4-d]pyrimidin-4-amine；3-(6-ethoxynaphthalen-2-yl)-1-(1-methylsulfonylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine
• CAS: 1363386-64-4
• 化学式: C₂₃H₂₆N₆O₃S
• 分子量: 466.564
• InChiKey: OJTHYXAIGLCWGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-羟基哌啶 在 四(三苯基膦)钯 、 水 、 sodium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 3-(6-ethoxynaphthalen-2-yl)-1-(1-(methylsulfonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Development of Toxoplasma gondii Calcium-Dependent Protein Kinase 1 (TgCDPK1) Inhibitors with Potent Anti-Toxoplasma Activity

  摘要：

  Toxoplasmosis is a disease of prominent health concern that is caused by the protozoan parasite Toxoplasma gondii. Proliferation of T. gondii is dependent on its ability to invade host cells, which is mediated in part by calcium-dependent protein kinase 1 (CDPK1). We have developed ATP competitive inhibitors of TgCDPK1 that block invasion of parasites into host cells, preventing their proliferation. The presence of a unique glycine gatekeeper residue in TgCDPK1 permits selective inhibition of the parasite enzyme over human kinases. These potent TgCDPK1 inhibitors do not inhibit the growth of human cell lines and represent promising candidates as toxoplasmosis therapeutics.

  DOI：

  10.1021/jm201713h

文献信息

• Development of <i>Toxoplasma gondii</i> Calcium-Dependent Protein Kinase 1 (<i>Tg</i>CDPK1) Inhibitors with Potent Anti-<i>Toxoplasma</i> Activity
  作者：Steven M. Johnson、Ryan C. Murphy、Jennifer A. Geiger、Amy E. DeRocher、Zhongsheng Zhang、Kayode K. Ojo、Eric T. Larson、B. Gayani K. Perera、Edward J. Dale、Panqing He、Molly C. Reid、Anna M. W. Fox、Natascha R. Mueller、Ethan A. Merritt、Erkang Fan、Marilyn Parsons、Wesley C. Van Voorhis、Dustin J. Maly

  DOI：10.1021/jm201713h

  日期：2012.3.8

  Toxoplasmosis is a disease of prominent health concern that is caused by the protozoan parasite Toxoplasma gondii. Proliferation of T. gondii is dependent on its ability to invade host cells, which is mediated in part by calcium-dependent protein kinase 1 (CDPK1). We have developed ATP competitive inhibitors of TgCDPK1 that block invasion of parasites into host cells, preventing their proliferation. The presence of a unique glycine gatekeeper residue in TgCDPK1 permits selective inhibition of the parasite enzyme over human kinases. These potent TgCDPK1 inhibitors do not inhibit the growth of human cell lines and represent promising candidates as toxoplasmosis therapeutics.