6-bromo-1,4-dihydroindeno[1,2-c]pyrazole | 760989-09-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 6-bromo-1,4-dihydroindeno[1,2-c]pyrazole
• 英文别名: 6-bromo-1,4-dihydro-indeno[1,2-c]pyrazole
• CAS: 760989-09-1
• 化学式: C₁₀H₇BrN₂
• 分子量: 235.083
• InChiKey: YZQUGDNNFDVLER-UHFFFAOYSA-N

物化性质

• 沸点：
  434.2±33.0 °C(Predicted)
• 密度：
  1.727±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-1,4-dihydroindeno[1,2-c]pyrazole 在 sodium chlorite 、 potassium dihydrogenphosphate 、 N-碘代丁二酰亚胺 、 氨基磺酸 、 仲丁基锂 、 苯基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.75h， 生成 3-iodo-1,4-dihydro-indeno[1,2-c]pyrazole-6-carboxylic acid
  参考文献：
  名称：

  Discovery of 1,4-dihydroindeno[1,2-c]pyrazoles as a novel class of potent and selective checkpoint kinase 1 inhibitors

  摘要：

  A new class of checkpoint kinase 1 (CHK-1) inhibitors bearing a 1,4-dihydroindeno[1,2-c]pyrazole core was developed after initial hits from high throughput screening. The efficient hit-to-lead process was facilitated by X-ray crystallography and led to potent inhibitors (< 10 nM) against CHK-1. X-ray co-crystal structures of bound inhibitors demonstrated that two sub-series of this class of compounds, exemplified by 21 and 41, exhibit distinctive hydrogen bonding patterns in the specificity pocket of the active site. Two compounds, 41 and 43, were capable of potentiating doxorubicin and camptothecin, both DNA-damaging agents, in cell proliferation assays (MTS and soft agar assays) and abrogating G2/M checkpoint in a mechanism-based FACS assay. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.012
• 作为产物：
  描述：

  在 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 以22%的产率得到6-bromo-1,4-dihydroindeno[1,2-c]pyrazole
  参考文献：
  名称：

  Non-oxime pyrazole based inhibitors of B-Raf kinase

  摘要：

  The synthesis and biological evaluation of non-oxime pyrazole based B-Raf inhibitors is reported. Several oxime replacements have been prepared and have shown excellent enzyme activity. Further optimization of fused pyrazole 2a led to compound 38, a selective and potent B-Raf inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.038

文献信息

• [EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2005095387A1

  公开（公告）日：2005-10-13

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物对抑制蛋白酪氨酸激酶具有用处。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用这些化合物进行治疗的方法。
• [EN] FUSED TRI AND TETRA-CYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PYRAZOLE KINASE FUSIONNEE TRICYCLIQUE ET TETRACYCLIQUE
  申请人：ABBOTT LAB

  公开号：WO2004080973A1

  公开（公告）日：2004-09-23

  Compounds having the formula (I) (I), are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有化学式(I) (I)的化合物对抑制蛋白激酶很有用。还公开了制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• Fused tri and tetra-cyclic pyrazole kinase inhibitors
  申请人：——

  公开号：US20040259904A1

  公开（公告）日：2004-12-23

  Compounds having the formula (I) 1 are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  化合物具有公式（I）1，对于抑制蛋白激酶具有用途。还公开了制备该化合物的方法，含有该化合物的组合物以及使用该化合物的治疗方法。
• Tricyclic pyrazole kinase inhibitors
  申请人：Arnold D. Lee

  公开号：US20060014816A1

  公开（公告）日：2006-01-19

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物可用于抑制蛋白酪氨酸激酶。还公开了制备该化合物的方法，含有该化合物的组合物，以及使用该化合物的治疗方法。
• A facile synthesis of antitumoral indeno[1,2-c]pyrazole-4-one by mild oxidation with molecular oxygen
  作者：Zhi-Fu Tao、Thomas J. Sowin、Nan-Horng Lin

  DOI：10.1016/j.tetlet.2005.08.147

  日期：2005.10

  An efficient, convenient, and general synthetic method for indeno[1,2-c]pyrazole-4-ones through oxidation of indeno-pyrazoles by treatment with a base and molecular oxygen is described, and a possible mechanism for the oxidation is proposed. The product indeno[1,2-c]pyrazole-4-ones were elaborated further by Suzuki coupling and Mitsunobu reaction. (c) 2005 Elsevier Ltd. All rights reserved.