5-(6-甲氧基喹啉-8-基氨基)戊腈 | 1061702-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5-(6-甲氧基喹啉-8-基氨基)戊腈
• 英文名称: 5-(6-methoxyquinolin-8-ylamino)pentanenitrile
• 英文别名: 5-[(6-Methoxy-8-quinolyl)amino]pentanenitrile；5-[(6-methoxyquinolin-8-yl)amino]pentanenitrile
• CAS: 1061702-76-8
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: RGVWYUGBZYDYJX-UHFFFAOYSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(6-甲氧基喹啉-8-基氨基)戊腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 AO-295/15484070
  参考文献：
  名称：

  氨基喹啉作为热休克蛋白 90 (Hsp90) 的一类新型强效抑制剂的发现：合成、生物学和分子建模。

  摘要：

  分子伴侣 Hsp90 在维持恶性表型中起重要作用。最近的研究表明，Hsp90 与多种癌蛋白产生高亲和力相互作用，这对肿瘤细胞的生长至关重要。因此，研究的重点是寻找 Hsp90 探针作为潜在和选择性的抗癌剂。在高通量筛选练习中，我们将喹啉 7 鉴定为 Hsp90 的中度抑制剂。进一步的命中识别、SAR 研究和生物学调查揭示了该系列中的几种合成类似物在荧光偏振 (FP) 测定和基于细胞的蛋白质印迹 (WB) 测定中均具有微摩尔活性。这些化合物代表了一类具有简单化学结构的新型 Hsp90 抑制剂。

  DOI：

  10.1016/j.bmc.2008.05.047
• 作为产物：
  描述：

  2-硝基-4-甲氧基苯胺 在 镍 arsenic(V) oxide 、 磷酸 、 氢气 、 三乙胺 作用下， 以 乙腈 为溶剂， 20.0~100.0 ℃ 、344.74 kPa 条件下， 反应 2.0h， 生成 5-(6-甲氧基喹啉-8-基氨基)戊腈
  参考文献：
  名称：

  8-aminoquinolines as anticoccidials - part III

  摘要：

  Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00393-5

文献信息

• 8-Aminoquinolines as anticoccidials — II
  作者：Richard E. Armer、Jacqueline S. Barlow、Christopher J. Dutton、David H.J. Greenway、Sean D.W. Greenwood、Nita Lad、Adrian P. Thompson、Kam-Wah Thong、Ivan Tommasini

  DOI：10.1016/s0960-894x(98)00243-1

  日期：1998.6

  During a chemistry program aimed at finding a novel analogue of pentaquine with improved in vivo activity, a number of hypotheses concerning the way this drug acts in the chicken were investigated. Consideration of the products of monoamine oxidase metabolism of pentaquine suggested that pentaquine aldehyde is the likely active metabolite. Although isolation of this unstable compound was not possible, oxime and cyclic acetal and ketal derivatives were obtained and shown to possess in vitro anticoccidial activity (C) 1998 Elsevier Science Ltd. All rights reserved.
• 8-aminoquinolines as anticoccidials - part III
  作者：Richard E. Armer、Jacqueline S. Barlow、Narinder Chopra、Christopher J. Dutton、David H.J. Greenway、Sean D.W. Greenwood、Nita Lad、Jonothan Shaw、Adrian P. Thompson、Kam-Wah Thong、Ivan Tommasini

  DOI：10.1016/s0960-894x(99)00393-5

  日期：1999.8

  Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Discovery of aminoquinolines as a new class of potent inhibitors of heat shock protein 90 (Hsp90): Synthesis, biology, and molecular modeling
  作者：Thota Ganesh、Jaeki Min、Pahk Thepchatri、Yuhong Du、Lian Li、Iestyn Lewis、Larry Wilson、Haian Fu、Gabriela Chiosis、Raymond Dingledine、Dennis Liotta、James P. Snyder、Aiming Sun

  DOI：10.1016/j.bmc.2008.05.047

  日期：2008.7

  The molecular chaperone Hsp90 plays important roles in maintaining malignant phenotypes. Recent studies suggest that Hsp90 exerts high-affinity interactions with multiple oncoproteins, which are essential for the growth of tumor cells. As a result, research has focused on finding Hsp90 probes as potential and selective anticancer agents. In a high-throughput screening exercise, we identified quinoline

  分子伴侣 Hsp90 在维持恶性表型中起重要作用。最近的研究表明，Hsp90 与多种癌蛋白产生高亲和力相互作用，这对肿瘤细胞的生长至关重要。因此，研究的重点是寻找 Hsp90 探针作为潜在和选择性的抗癌剂。在高通量筛选练习中，我们将喹啉 7 鉴定为 Hsp90 的中度抑制剂。进一步的命中识别、SAR 研究和生物学调查揭示了该系列中的几种合成类似物在荧光偏振 (FP) 测定和基于细胞的蛋白质印迹 (WB) 测定中均具有微摩尔活性。这些化合物代表了一类具有简单化学结构的新型 Hsp90 抑制剂。