Seleno-1 Coumarine | 4764-21-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Seleno-1 Coumarine
• 英文别名: selenacoumarin；2H-selenochromen-2-one；Selenocumarin；Seleno-1-coumarin；selenochromen-2-one；1-Seleno-cumarin
• CAS: 4764-21-0
• 化学式: C₉H₆OSe
• 分子量: 209.106
• InChiKey: MQVUKGJIKAKFFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  11
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Seleno-1 Coumarine 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以87%的产率得到2H-selenochromene-2-thione
  参考文献：
  名称：

  Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

  摘要：

  We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

  DOI：

  10.1021/acsmedchemlett.8b00362
• 作为产物：
  描述：

  3-phenyl propenoic acid selenophenyl ester 在 aluminum (III) chloride 作用下， 以 氯苯 为溶剂， 反应 0.5h， 以70%的产率得到Seleno-1 Coumarine
  参考文献：
  名称：

  Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

  摘要：

  We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

  DOI：

  10.1021/acsmedchemlett.8b00362

文献信息

• Jayachandran, T.; Manimaran, T.; Ramakrishnan, V. T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 4, p. 328 - 330
  作者：Jayachandran, T.、Manimaran, T.、Ramakrishnan, V. T.

  DOI：——

  日期：——
• JAYACHANDRAN, T.;MANIMARAN, T.;RAMAKRISHNAN, V. T., INDIAN J. CHEM., 1984, 23, N 4, 328-330
  作者：JAYACHANDRAN, T.、MANIMARAN, T.、RAMAKRISHNAN, V. T.

  DOI：——

  日期：——
• Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines
  作者：Andrea Angeli、Elena Trallori、Fabrizio Carta、Lorenzo Di Cesare Mannelli、Carla Ghelardini、Claudiu T. Supuran

  DOI：10.1021/acsmedchemlett.8b00362

  日期：2018.9.13

  We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.