1-methyl-10H-indeno[1,2-g]quinolinium; iodide | 97810-95-2

• 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: 1-methyl-10H-indeno[1,2-g]quinolinium; iodide
• 英文别名: 1-Methyl-10H-indeno[1,2-g]chinolinium; Jodid；5-methyl-11H-indeno[1,2-b]quinolin-5-ium;iodide
• CAS: 97810-95-2
• 化学式: C₁₇H₁₄N*I
• 分子量: 359.209
• InChiKey: MAQPCODDWXOAAX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  10-chloro-11H-indeno[1,2-b]quinoline 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 环丁砜 为溶剂， 110.0 ℃ 、344.74 kPa 条件下， 反应 18.0h， 生成 1-methyl-10H-indeno[1,2-g]quinolinium; iodide
  参考文献：
  名称：

  Synthesis and evaluation of isosteres of N-methyl indolo[3,2-b]-quinoline (cryptolepine) as new antiinfective agents

  摘要：

  Isosteres of cryptolepine (1) were synthesized and evaluated for their antiinfective activities. Overall, the sulfur isostere, 5-methyl benzothieno[3,2-b]quinolinium salt (5b), was equipotent to 1 and has shown no cytotoxicity at 23.8 mu g/mL. Compound 5b was also found to have a broad spectrum of activity. Both the carbon and oxygen isosteres were less potent than cryptolepine. A limited library of 2-substituted analogs of 5b has been synthesized and evaluated in antifungal screens but did not show increase in potency compared to the unsubstituted 5b. Similarly, evaluation of tricyclic benzothieno[3,2-b]pyridines while showing promise in individual screens did not produce an overall increase in potency. Overall, the evaluation of the activities of 5b compared with standard antifungal/anti-protozoal agents suggests that the benzothienoquinoline scaffold could serve as a lead for optimization. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.062

文献信息

• Diels; Staehlin, Chemische Berichte, 1902, vol. 35, p. 3275,3282
  作者：Diels、Staehlin

  DOI：——

  日期：——
• Synthesis and evaluation of isosteres of N-methyl indolo[3,2-b]-quinoline (cryptolepine) as new antiinfective agents
  作者：Xue Y. Zhu、Leroy G. Mardenborough、Shouming Li、Abdul Khan、Wang Zhang、Pincheng Fan、Melissa Jacob、Shabana Khan、Larry Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2006.10.062

  日期：2007.1

  Isosteres of cryptolepine (1) were synthesized and evaluated for their antiinfective activities. Overall, the sulfur isostere, 5-methyl benzothieno[3,2-b]quinolinium salt (5b), was equipotent to 1 and has shown no cytotoxicity at 23.8 mu g/mL. Compound 5b was also found to have a broad spectrum of activity. Both the carbon and oxygen isosteres were less potent than cryptolepine. A limited library of 2-substituted analogs of 5b has been synthesized and evaluated in antifungal screens but did not show increase in potency compared to the unsubstituted 5b. Similarly, evaluation of tricyclic benzothieno[3,2-b]pyridines while showing promise in individual screens did not produce an overall increase in potency. Overall, the evaluation of the activities of 5b compared with standard antifungal/anti-protozoal agents suggests that the benzothienoquinoline scaffold could serve as a lead for optimization. (c) 2006 Elsevier Ltd. All rights reserved.