8-nitrobenzo[4,5]thieno[3,2-b]pyridine | 83702-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 8-nitrobenzo[4,5]thieno[3,2-b]pyridine
• 英文别名: 7-Nitrobenzothiopheno<3,2-b>pyridine；8-Nitro-[1]benzothiolo[3,2-b]pyridine
• CAS: 83702-41-4
• 化学式: C₁₁H₆N₂O₂S
• 分子量: 230.247
• InChiKey: ILMDHKBZYLOOEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-nitrobenzo[4,5]thieno[3,2-b]pyridine 在 盐酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 51.5h， 生成 Benzothieno<3,2-b>pyridine
  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：

  3-Bromo-2-(2-hydroxy-5-nitrophenyl)pyridine 在 氢氧化钾 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 2.75h， 生成 8-nitrobenzo[4,5]thieno[3,2-b]pyridine
  参考文献：
  名称：

  Abramovitch, Rudolph A.; Inbasekaran, Muthiah N.; Miller, Adrian L., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 509 - 512

  摘要：

  DOI：

文献信息

• ABRAMOVITCH, R. A.;INBASEKARAN, M. N.;MILLER, A. L.;HANNA, J. M. ,, JR, J. HETEROCYCL. CHEM., 1982, 19, N 3, 509-512
  作者：ABRAMOVITCH, R. A.、INBASEKARAN, M. N.、MILLER, A. L.、HANNA, J. M. ,, JR

  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.
• Abramovitch, Rudolph A.; Inbasekaran, Muthiah N.; Miller, Adrian L., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 509 - 512
  作者：Abramovitch, Rudolph A.、Inbasekaran, Muthiah N.、Miller, Adrian L.、Hanna, James M.

  DOI：——

  日期：——