6-bromoisoquinoline-5,8-dione | 1383471-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-bromoisoquinoline-5,8-dione
• CAS: 1383471-24-6
• 化学式: C₉H₄BrNO₂
• 分子量: 238.04
• InChiKey: JHGARYABFBPOLY-UHFFFAOYSA-N

物化性质

• 沸点：
  355.5±42.0 °C(Predicted)
• 密度：
  1.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromoisoquinoline-5,8-dione 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以30%的产率得到7-氨基异喹啉-5,8-二酮
  参考文献：
  名称：

  Abdelwahab, Ahmed B.; Shaaban, Mohamed; Ismail, Mohamed A.H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 8, p. 1098 - 1109

  摘要：

  DOI：
• 作为产物：
  描述：

  5-amino-6,8-dibromoisoquinoline 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 6-bromoisoquinoline-5,8-dione
  参考文献：
  名称：

  Abdelwahab, Ahmed B.; Shaaban, Mohamed; Ismail, Mohamed A.H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 8, p. 1098 - 1109

  摘要：

  DOI：

文献信息

• The synthesis of furoquinolinedione and isoxazoloquinolinedione derivatives as selective Tyrosyl-DNA phosphodiesterase 2 (TDP2) inhibitors
  作者：Hao Yang、Xiao-Qing Zhu、Wenjie Wang、Yu Chen、Zhu Hu、Yu Zhang、De-Xuan Hu、Le-Mao Yu、Keli Agama、Yves Pommier、Lin-Kun An

  DOI：10.1016/j.bioorg.2021.104881

  日期：2021.6

  Based on our previous study on the development of the furoquinolinedione and isoxazoloquinolinedione TDP2 inhibitors, the further structure-activity relationship (SAR) was studied in this work. A series of furoquinolinedione and isoxazoloquinolinedione derivatives were synthesized and tested for enzyme inhibitions. Enzyme-based assays indicated that isoxazoloquinolinedione derivatives selectively showed

  基于我们之前对呋喃喹啉二酮和异恶唑并喹啉二酮 TDP2 抑制剂开发的研究，本工作进一步研究了构效关系 (SAR)。合成了一系列呋喃喹啉二酮和异恶唑并喹啉二酮衍生物并测试了酶抑制作用。基于酶的测定表明，异恶唑并喹啉二酮衍生物在亚微摩尔范围内选择性地显示出高 TDP2 抑制活性，呋喃喹啉二酮衍生物在低微摩尔范围内选择性地显示出高 TDP2 抑制活性。最有效的 3-(3,4-二甲氧基苯基) 异恶唑并[4,5-g]喹啉-4,9-二酮 ( 70 ) 显示出 TDP2 抑制活性，IC 50为 0.46 ± 0.15 μM。这项工作将促进未来发现异恶唑并喹啉二酮 TDP2 选择性抑制剂的努力。
• Isoxazolo(aza)naphthoquinones: A new class of cytotoxic Hsp90 inhibitors
  作者：Alberto Bargiotti、Loana Musso、Sabrina Dallavalle、Lucio Merlini、Grazia Gallo、Andrea Ciacci、Giuseppe Giannini、Walter Cabri、Sergio Penco、Loredana Vesci、Massimo Castorina、Ferdinando Maria Milazzo、Maria Luisa Cervoni、Marcella Barbarino、Claudio Pisano、Chiara Giommarelli、Valentina Zuco、Michelandrea De Cesare、Franco Zunino

  DOI：10.1016/j.ejmech.2012.03.036

  日期：2012.7

  A series of 3-aryl-naphtho[2,3-d]isoxazole-4,9-diones and some of their 6-aza analogues were Synthesized and found to inhibit the heat shock protein 90 (Hsp90). The compounds were tested for their binding to Hsp90 and for their effects on Hsp90 client proteins expression in a series of human tumour cell lines. Representative compounds (7f, 10c) downregulated the Hsp90 client proteins EGFR, Akt, Cdk4, Raf-1, and survivin, and upregulated Hsp70. Most of the compounds, in particular the alkylated 3-pyridyl derivatives, exhibited potent antiproliferative activity, down to two-digit nanomolar range. Preliminary results indicated in vivo activity of 7f against human epithelial carcinoma A431 model growing as tumour xenograft in nude mice, thus supporting the therapeutic potential of this novel series of Hsp90 inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.