4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl trifluoromethanesulfonate | 622862-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl trifluoromethanesulfonate
• 英文别名: [4-(2-chlorophenyl)-9-methoxy-1,3-dioxo-6H-pyrrolo[3,4-g]carbazol-8-yl] trifluoromethanesulfonate
• CAS: 622862-86-6
• 化学式: C₂₂H₁₂ClF₃N₂O₆S
• 分子量: 524.861
• InChiKey: FXQBJPZXOVFEBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl trifluoromethanesulfonate 、 (E)-4-(tributylstannyl)but-3-en-1-ol 在 bis-triphenylphosphine-palladium(II) chloride lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-Chlorophenyl)-8-[(1E)-4-hydroxy-1-butenyl]-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of soluble 8-substituted 4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as inhibitors of the Wee1 and Chk1 checkpoint kinases

  摘要：

  Pyrrolo[3,4-c]carbazoles bearing solubilising basic side chains at the 8-position retain potent Weel and Chk1 inhibitory properties in isolated enzyme assays, and evidence of G2/M checkpoint abrogation in several cellular assays. Co-crystal structure studies confirm that the primary binding to the Weel enzyme is as described previously, with the C-8 side chains residing in an area of bulk tolerance. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.046
• 作为产物：
  描述：

  4-(2-Chlorophenyl)-8-hydroxy-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 、 三氟甲磺酸酐 以gave the triflate (169) (87%) as a yellow solid, mp 248–252° C的产率得到4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Inhibitors of checkpoint kinases (Wee1 and Chk1)

  摘要：

  本发明涉及公式I中的吡咯烷并咔唑衍生物，其中R1、R2、R7、R8、R9、X和Y如规范中所定义，其中这些衍生物特异性抑制检查点激酶Wee1和Chk1中的一个或两个。

  公开号：

  US07094798B1

文献信息

• Inhibitors of checkpoint kinases (Wee1 and Chk1)
  申请人：Pfizer Inc

  公开号：US07094798B1

  公开（公告）日：2006-08-22

  This invention relates to pyrrolocarbazole derivatives according formula I wherein R1, R2, R7, R8, R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1

  本发明涉及公式I中的吡咯烷并咔唑衍生物，其中R1、R2、R7、R8、R9、X和Y如规范中所定义，其中这些衍生物特异性抑制检查点激酶Wee1和Chk1中的一个或两个。
• US7094798B1
  申请人：——

  公开号：US7094798B1

  公开（公告）日：2006-08-22
• Synthesis and structure–activity relationships of soluble 8-substituted 4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as inhibitors of the Wee1 and Chk1 checkpoint kinases
  作者：Jeff B. Smaill、Ho H. Lee、Brian D. Palmer、Andrew M. Thompson、Christopher J. Squire、Edward N. Baker、R. John Booth、Alan Kraker、Ken Hook、William A. Denny

  DOI：10.1016/j.bmcl.2007.12.046

  日期：2008.2

  Pyrrolo[3,4-c]carbazoles bearing solubilising basic side chains at the 8-position retain potent Weel and Chk1 inhibitory properties in isolated enzyme assays, and evidence of G2/M checkpoint abrogation in several cellular assays. Co-crystal structure studies confirm that the primary binding to the Weel enzyme is as described previously, with the C-8 side chains residing in an area of bulk tolerance. (C) 2007 Elsevier Ltd. All rights reserved.