11-chloro-7-methyl-10H-indolo[3,2-b]quinoline | 131058-41-8

• 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
• 英文名称: 11-chloro-7-methyl-10H-indolo[3,2-b]quinoline
• CAS: 131058-41-8
• 化学式: C₁₆H₁₁ClN₂
• 分子量: 266.73
• InChiKey: HHQQSPDCOUSBMF-UHFFFAOYSA-N

物化性质

• 沸点：
  504.7±45.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  对氨基苯酚 、 11-chloro-7-methyl-10H-indolo[3,2-b]quinoline 在 盐酸 作用下， 以 乙二醇乙醚 、 水 为溶剂， 反应 3.0h， 以48%的产率得到4-((7-methyl-10H-indolo[3,2-b]quinolin-11-yl)amino)phenol
  参考文献：
  名称：

  Structure–activity relationship of indoloquinoline analogs anti-MRSA

  摘要：

  Indolo[3,2-b]quinoline analogs (3a-3s), 4-(acridin-9-ylamino) phenol hydrochloride (4), benzofuro[3,2-b]quinoline (3t), indeno[1,2-b] quinolines (3u and 3v) have been synthesized. Those compounds were found to exhibit anti-bacterial activity towards Methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship studies were conducted that indoloquinoline ring, benzofuro-quinoline ring and 4-aminophenol group are essential structure for anti-MRSA activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.058
• 作为产物：
  描述：

  邻氨基苯甲酸 在 三氟化硼乙醚 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.17h， 生成 11-chloro-7-methyl-10H-indolo[3,2-b]quinoline
  参考文献：
  名称：

  Structure–activity relationship of indoloquinoline analogs anti-MRSA

  摘要：

  Indolo[3,2-b]quinoline analogs (3a-3s), 4-(acridin-9-ylamino) phenol hydrochloride (4), benzofuro[3,2-b]quinoline (3t), indeno[1,2-b] quinolines (3u and 3v) have been synthesized. Those compounds were found to exhibit anti-bacterial activity towards Methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship studies were conducted that indoloquinoline ring, benzofuro-quinoline ring and 4-aminophenol group are essential structure for anti-MRSA activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.058

文献信息

• Synthesis and Antitumor Activity of Fused Quinoline Derivatives. V. Methylindolo(3,2-b)quinolines.
  作者：Yasuo TAKEUCHI、Masayuki KITAOMO、Ming-rong CHANG、Shota SHIRASAKA、Chinami SHIMAMURA、Yumiko OKUNO、Masatoshi YAMATO、Takashi HARAYAMA

  DOI：10.1248/cpb.45.2096

  日期：——

  Indolo[3,2-b]quinoline derivatives (1b-i) with a methyl group at each possible position have been synthesized. The 1-methyl (1b) and 9-methyl (1i) derivatives were inactive, but the 3-methyl (1d), 4-methyl (1e), and 6-methyl (1f) derivatives exhibited high treatment/control (T/C) value and cure rates against leukemia P388 in mice. These results indicated that modification of indolo[3,2-b]quinoline

  合成了在每个可能位置具有甲基的吲哚并[3,2-b]喹啉衍生物（1b-i）。1-甲基（1b）和9-甲基（1i）衍生物没有活性，但是3-甲基（1d），4-甲基（1e）和6甲基（1f）衍生物表现出较高的处理/控制（T / C）小鼠抗白血病P388的价值和治愈率。这些结果表明，吲哚[3,2-b]喹啉衍生物在3、4和6位的修饰可能是优化前导的有用方法。
• Chang, Ming-rong; Takeuchi, Yasuo; Hashigaki, Kuniko, Heterocycles, 1992, vol. 33, # 1, p. 147 - 152
  作者：Chang, Ming-rong、Takeuchi, Yasuo、Hashigaki, Kuniko、Yamato, Masatoshi

  DOI：——

  日期：——
• US5741926A
  申请人：——

  公开号：US5741926A

  公开（公告）日：1998-04-21
• Structure–activity relationship of indoloquinoline analogs anti-MRSA
  作者：Min Zhao、Tomonori Kamada、Aya Takeuchi、Hiromi Nishioka、Teruo Kuroda、Yasuo Takeuchi

  DOI：10.1016/j.bmcl.2015.10.058

  日期：2015.12

  Indolo[3,2-b]quinoline analogs (3a-3s), 4-(acridin-9-ylamino) phenol hydrochloride (4), benzofuro[3,2-b]quinoline (3t), indeno[1,2-b] quinolines (3u and 3v) have been synthesized. Those compounds were found to exhibit anti-bacterial activity towards Methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship studies were conducted that indoloquinoline ring, benzofuro-quinoline ring and 4-aminophenol group are essential structure for anti-MRSA activity. (C) 2015 Elsevier Ltd. All rights reserved.