7-methoxy-4-mercaptomethylcoumarin | 501002-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-methoxy-4-mercaptomethylcoumarin
• 英文别名: 7-Methoxy-4-(sulfanylmethyl)chromen-2-one
• CAS: 501002-57-9
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: TXVRUYVCAOZKOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-4-mercaptomethylcoumarin 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到SV₂₅
  参考文献：
  名称：

  Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells

  摘要：

  Coumarins and coumarin derivatives as well as diallyl polysulfides are well known as anticancer drugs. In order to find new drugs with anticancer activities, we combined coumarins with polysulfides in the form of di-coumarin polysulfides. These novel compounds were tested in the HCT116 colorectal cancer cell line. It turned out that they reduced cell viability of cancer cells in a time and concentration dependent manner. Cells tested with these coumarin polysulfides accumulate in the G(2)/M phase of the cell cycle and finally they go into apoptosis. A decrease in bcl-2 level, and increase in the level of bax, cytochrome c release into the cytosol, cleavage of caspase 3/7and PARP suggested that coumarin polysulfides induced the intrinsic pathway of apoptosis. Comparison of these new coumarin compounds with the well known diallyl polysulfides revealed that the coumarin disulfides were more active than the corresponding diallyl disulfides. The activities of the coumarin tetrasulfides and the corresponding diallyl tetrasulfides are similar. The novel coumarin compounds regulated the phosphatase activity of the cell cycle regulating cdc25 family members, indicating that these phosphatases are implicated in the induction of cell cycle arrest and possibly in apoptosis induction as well. In addition, coumarin polysulfides also down-regulated the level of cdc25C, which also contributed to the arrest in the G(2)-phase of the cell cycle. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.032
• 作为产物：
  描述：

  4-氯甲基-7-甲氧基色烯-2-酮 在 硫脲 作用下， 以 乙醚 、 乙醇 为溶剂， 以75%的产率得到7-methoxy-4-mercaptomethylcoumarin
  参考文献：
  名称：

  Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells

  摘要：

  Coumarins and coumarin derivatives as well as diallyl polysulfides are well known as anticancer drugs. In order to find new drugs with anticancer activities, we combined coumarins with polysulfides in the form of di-coumarin polysulfides. These novel compounds were tested in the HCT116 colorectal cancer cell line. It turned out that they reduced cell viability of cancer cells in a time and concentration dependent manner. Cells tested with these coumarin polysulfides accumulate in the G(2)/M phase of the cell cycle and finally they go into apoptosis. A decrease in bcl-2 level, and increase in the level of bax, cytochrome c release into the cytosol, cleavage of caspase 3/7and PARP suggested that coumarin polysulfides induced the intrinsic pathway of apoptosis. Comparison of these new coumarin compounds with the well known diallyl polysulfides revealed that the coumarin disulfides were more active than the corresponding diallyl disulfides. The activities of the coumarin tetrasulfides and the corresponding diallyl tetrasulfides are similar. The novel coumarin compounds regulated the phosphatase activity of the cell cycle regulating cdc25 family members, indicating that these phosphatases are implicated in the induction of cell cycle arrest and possibly in apoptosis induction as well. In addition, coumarin polysulfides also down-regulated the level of cdc25C, which also contributed to the arrest in the G(2)-phase of the cell cycle. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.032

文献信息

• Gold(I)-Complex-Titania Hybrid Photocatalyst for Hydrogen Production
  作者：Elisabet Aguiló、Lluís Soler、Albert Casanovas、Artur J. Moro、João Carlos Lima、Laura Rodríguez、Jordi Llorca

  DOI：10.1002/cctc.201700518

  日期：2017.9.8

  very efficient photocatalyst for the generation of H2. The molecular structure of the complex was preserved under the photoreaction owing to the strong AuI−S bond. The AuI complex played a determinant role in the photogeneration of H2 by accepting the photoinduced electrons originated in TiO2 upon light exposure. This is the first example of a AuI complex semiconductor hybrid photocatalyst. The rate of

  TiO 2与包含硫代香豆素部分的Au I络合物的结合产生了非常有效的光催化剂，用于产生H 2。由于强的Au I -S键，复合物的分子结构在光反应下得以保留。Au I络合物通过接受曝光后源自TiO 2的光致电子，在H 2的光生中起决定性作用。这是Au I络合物半导体混合光催化剂的第一个例子。H 2的比率在动态条件下由水/乙醇产生的金属在金属基础上比由金金属纳米粒子装饰的常规TiO 2约高一个数量级。
• Synthesis and biological evaluation of novel coumarin-based inhibitors of Cdc25 phosphatases
  作者：Sergio Valente、Emilie Bana、Elodie Viry、Denyse Bagrel、Gilbert Kirsch

  DOI：10.1016/j.bmcl.2010.07.130

  日期：2010.10

  The cell division cycle 25 (Cdc25) family of proteins are dual specificity phosphatases that activate cyclin-dependent kinase (CDK) complexes, which in turn regulate progression through the cell division cycle. Overexpression of Cdc25 proteins has been reported in a wide variety of cancers; their inhibition may thus represent a novel approach for the development of anticancer therapeutics. Herein we report new coumarin-based scaffolds endowed with a selective inhibition against Cdc25A and Cdc25C, being 6a and 6d the most efficient inhibitors and worthy of further investigation as anticancer agents. (C) 2010 Elsevier Ltd. All rights reserved.
• Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells
  作者：Nathaniel Edward Bennett Saidu、Sergio Valente、Emilie Bana、Gilbert Kirsch、Denyse Bagrel、Mathias Montenarh

  DOI：10.1016/j.bmc.2011.12.032

  日期：2012.2

  Coumarins and coumarin derivatives as well as diallyl polysulfides are well known as anticancer drugs. In order to find new drugs with anticancer activities, we combined coumarins with polysulfides in the form of di-coumarin polysulfides. These novel compounds were tested in the HCT116 colorectal cancer cell line. It turned out that they reduced cell viability of cancer cells in a time and concentration dependent manner. Cells tested with these coumarin polysulfides accumulate in the G(2)/M phase of the cell cycle and finally they go into apoptosis. A decrease in bcl-2 level, and increase in the level of bax, cytochrome c release into the cytosol, cleavage of caspase 3/7and PARP suggested that coumarin polysulfides induced the intrinsic pathway of apoptosis. Comparison of these new coumarin compounds with the well known diallyl polysulfides revealed that the coumarin disulfides were more active than the corresponding diallyl disulfides. The activities of the coumarin tetrasulfides and the corresponding diallyl tetrasulfides are similar. The novel coumarin compounds regulated the phosphatase activity of the cell cycle regulating cdc25 family members, indicating that these phosphatases are implicated in the induction of cell cycle arrest and possibly in apoptosis induction as well. In addition, coumarin polysulfides also down-regulated the level of cdc25C, which also contributed to the arrest in the G(2)-phase of the cell cycle. (C) 2011 Elsevier Ltd. All rights reserved.