3-(6-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)phenol | 1058193-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3-(6-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)phenol
• 英文别名: 3-[6-Methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol；3-(6-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)phenol
• CAS: 1058193-84-2
• 化学式: C₁₇H₁₇N₃O₂S
• 分子量: 327.407
• InChiKey: IAAWZHBLOYYROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羟基苯硼酸 、 2-chloro-6-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 4.0h， 以10%的产率得到3-(6-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)phenol
  参考文献：
  名称：

  The Identification of 2-(1H-Indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (GDC-0941) as a Potent, Selective, Orally Bioavailable Inhibitor of Class I PI3 Kinase for the Treatment of Cancer

  摘要：

  Phosphatidylinositol-3-kinase (PI3K) is an important target in cancer due to the deregulation of the PI3K/ Akt signaling pathway in a wide variety of tumors. A series of thieno[3,2-d]pyrimidine derivatives were prepared and evaluated as inhibitors of PI3 kinase p110alpha. The synthesis, biological activity, and further profiling of these compounds are described. This work resulted in the discovery of 17, GDC-0941, which is a potent, selective, orally bioavailable inhibitor of PI3K and is currently being evaluated in human clinical trials for the treatment of cancer.

  DOI：

  10.1021/jm800295d

文献信息

• [EN] LIGAND-DIRECTED COVALENT MODIFICATION OF PROTEIN<br/>[FR] MODIFICATION COVALENTE DE PROTÉINE, DIRIGÉE SUR UN LIGAND
  申请人：AVILA THERAPEUTICS INC

  公开号：WO2011082285A1

  公开（公告）日：2011-07-07

  The present invention relates to enzyme inhibitors. More specifically, the present invention relates to ligand-directed covalent modification of proteins; method of designing same; pharmaceutical formulation of same; and method of use.
• The Identification of 2-(1<i>H</i>-Indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-<i>d</i>]pyrimidine (GDC-0941) as a Potent, Selective, Orally Bioavailable Inhibitor of Class I PI3 Kinase for the Treatment of Cancer
  作者：Adrian J. Folkes、Khatereh Ahmadi、Wendy K. Alderton、Sonia Alix、Stewart J. Baker、Gary Box、Irina S. Chuckowree、Paul A. Clarke、Paul Depledge、Suzanne A. Eccles、Lori S. Friedman、Angela Hayes、Timothy C. Hancox、Arumugam Kugendradas、Letitia Lensun、Pauline Moore、Alan G. Olivero、Jodie Pang、Sonal Patel、Giles H. Pergl-Wilson、Florence I. Raynaud、Anthony Robson、Nahid Saghir、Laurent Salphati、Sukhjit Sohal、Mark H. Ultsch、Melanie Valenti、Heidi J.A. Wallweber、Nan Chi Wan、Christian Wiesmann、Paul Workman、Alexander Zhyvoloup、Marketa J. Zvelebil、Stephen J. Shuttleworth

  DOI：10.1021/jm800295d

  日期：2008.9.25

  Phosphatidylinositol-3-kinase (PI3K) is an important target in cancer due to the deregulation of the PI3K/ Akt signaling pathway in a wide variety of tumors. A series of thieno[3,2-d]pyrimidine derivatives were prepared and evaluated as inhibitors of PI3 kinase p110alpha. The synthesis, biological activity, and further profiling of these compounds are described. This work resulted in the discovery of 17, GDC-0941, which is a potent, selective, orally bioavailable inhibitor of PI3K and is currently being evaluated in human clinical trials for the treatment of cancer.