10-Oxo-5,10-dihydro-11-thia-5-aza-benzo[b]fluorene-8-carbonitrile | 919832-56-7

• 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: 10-Oxo-5,10-dihydro-11-thia-5-aza-benzo[b]fluorene-8-carbonitrile
• CAS: 919832-56-7
• 化学式: C₁₆H₈N₂OS
• 分子量: 276.318
• InChiKey: NVQUEBDZWDNBCH-UHFFFAOYSA-N

物化性质

• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.65
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  10-Oxo-5,10-dihydro-11-thia-5-aza-benzo[b]fluorene-8-carbonitrile 在 palladium on activated charcoal 硫酸 、 氢气 、 溶剂黄146 、 三氯氧磷 作用下， 以 环丁砜 、 水 为溶剂， 20.0~110.0 ℃ 、448.16 kPa 条件下， 反应 54.0h， 生成 5-Methyl-[1]benzothiolo[3,2-b]quinolin-5-ium-2-carboxylic acid;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
• 作为产物：
  描述：

  5-Iodo-2-[(2-phenylsulfanylacetyl)amino]benzoic acid 在 PPA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 10-Oxo-5,10-dihydro-11-thia-5-aza-benzo[b]fluorene-8-carbonitrile
  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