3-iodo-1,4-dihydro-indeno[1,2-c]pyrazole-6-carboxylic acid | 760989-85-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-iodo-1,4-dihydro-indeno[1,2-c]pyrazole-6-carboxylic acid
• 英文别名: 3-Iodo-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxylic acid；3-iodo-2,4-dihydroindeno[1,2-c]pyrazole-6-carboxylic acid
• CAS: 760989-85-3
• 化学式: C₁₁H₇IN₂O₂
• 分子量: 326.093
• InChiKey: YFQZQGRALWDHCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  588.6±50.0 °C(Predicted)
• 密度：
  2?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-iodo-1,4-dihydro-indeno[1,2-c]pyrazole-6-carboxylic acid 、 trans-4-Aminocyclohexanol 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  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：

  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

文献信息

• [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。
• US7320986B2
  申请人：——

  公开号：US7320986B2

  公开（公告）日：2008-01-22