6-methoxy-3-(thiophen-2-yl)coumarin | 1296150-45-2

• 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: 6-methoxy-3-(thiophen-2-yl)coumarin
• 英文别名: 6-methoxy-3-thiophen-2-ylchromen-2-one
• CAS: 1296150-45-2
• 化学式: C₁₄H₁₀O₃S
• 分子量: 258.298
• InChiKey: XEXBSPAKFREWBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 6-methoxy-3-(thiophen-2-yl)coumarin
  参考文献：
  名称：

  Synthesis, human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives

  摘要：

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Series of 3-indolyl and 3-thiophenylcoumarins were synthesized and evaluated as inhibitors of the two human MAO isoforms, hMAO-A and hMAO-B. In general, the derivatives were found to be selective hMAO-B inhibitors with IC(50) values in the nanoMolar (nM) to microMolar (mu M) range. Docking experiments were carried out in order to compare the theoretical and experimental affinity of these compounds to the hMAO-B protein. According to our results, docking experiments could be an interesting approach to try to predict the activity of this class of coumarins against MAO-B receptors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.033

文献信息

• New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: Anti-melanogenesis and antioxidant activities, and computational molecular modeling studies
  作者：Francesca Pintus、Maria J. Matos、Santiago Vilar、George Hripcsak、Carla Varela、Eugenio Uriarte、Lourdes Santana、Fernanda Borges、Rosaria Medda、Amalia Di Petrillo、Benedetta Era、Antonella Fais

  DOI：10.1016/j.bmc.2017.01.037

  日期：2017.3

  Melanogenesis is a physiological pathway for the formation of melanin. Tyrosinase catalyzes the first step of this process and down-regulation of its activity is responsible for the inhibition of melanogenesis. The search for molecules capable of controlling hyperpigmentation is a trend topic in health and cosmetics. A series of heteroarylcoumarins have been synthesized and evaluated. Compounds 4 and 8 exhibited higher tyrosinase inhibitory activities (IC50 = 0.15 and 0.38 mu M, respectively), than the reference compound, kojic acid (IC50 = 17.9 mu M). Compound 4 acts as competitive, while compound 8 as uncompetitive inhibitor of mushroom tyrosinase. Furthermore, compounds 2 and 8 inhibited tyrosinase activity and melanin production in B16F10 cells. In addition, compounds 2-4 and 8 proved to have an interesting antioxidant profile in both ABTS and DPPH radicals scavenging assays. Docking experiments were carried out in order to study the interactions between these heteroarylcoumarins and mushroom tyrosinase. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis, human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives
  作者：Giovanna Delogu、Carmen Picciau、Giulio Ferino、Elías Quezada、Gianni Podda、Eugenio Uriarte、Dolores Viña

  DOI：10.1016/j.ejmech.2011.01.033

  日期：2011.4

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Series of 3-indolyl and 3-thiophenylcoumarins were synthesized and evaluated as inhibitors of the two human MAO isoforms, hMAO-A and hMAO-B. In general, the derivatives were found to be selective hMAO-B inhibitors with IC(50) values in the nanoMolar (nM) to microMolar (mu M) range. Docking experiments were carried out in order to compare the theoretical and experimental affinity of these compounds to the hMAO-B protein. According to our results, docking experiments could be an interesting approach to try to predict the activity of this class of coumarins against MAO-B receptors. (C) 2011 Elsevier Masson SAS. All rights reserved.