3-bromo-4-(2-methoxy-4-fluorophenyl)furan-2(5H)-one | 1402571-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-4-(2-methoxy-4-fluorophenyl)furan-2(5H)-one
• 英文别名: 4-bromo-3-(4-fluoro-2-methoxyphenyl)-2H-furan-5-one
• CAS: 1402571-22-5
• 化学式: C₁₁H₈BrFO₃
• 分子量: 287.085
• InChiKey: VIHQQHFUUBHRTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(2-methoxy-4-fluorophenyl)furan-2(5H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-bromo-5-(4-fluoro-2-methoxyphenyl)-2-(3-nitrophenyl)-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Cyclopent-4-ene-1,3-diones: A New Class of Herbicides Acting as Potent Photosynthesis Inhibitors

  摘要：

  In a recent paper, we reported the synthesis and photosynthesis-inhibitory activity of a series of analogues of rubrolides. From quantitative structure-activity relationship (QSAR) studies, we found that the most efficient compounds are those having higher ability to accept electrons. On the basis of those findings, we directed our effort to synthesize new analogues bearing a strong electron-withdrawing group (nitro) in the benzylidene ring and evaluate their effects on photosynthesis. However, the employed synthetic approach led to novel cyclopent-4-ene-1,3-diones as major products. Here, we report the synthesis and mechanism of action of such cyclopent-4-ene-1,3-diones as a new class of photosynthesis inhibitors. These compounds block the electron transport at the QB level by interacting at the D1 protein at the reducing side of Photosystem II and act as Hill reaction inhibitors, with higher activity than the corresponding rubrolides. To the best of our knowledge, this is the first report on the photosynthesis inhibitory activity of cyclopentenediones.

  DOI：

  10.1021/jf5014605
• 作为产物：
  描述：

  3,4-二溴呋喃-2(5H)-酮 、 4-氟-2-甲氧基苯硼酸 在 双(乙腈)氯化钯(II) 、 三苯胂 、 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 以51 %的产率得到3-bromo-4-(2-methoxy-4-fluorophenyl)furan-2(5H)-one
  参考文献：
  名称：

  作为脲酶抑制剂的红溴内酯类似物

  摘要：

  脲酶是幽门螺杆菌在胃粘膜定植和感染过程中的重要毒力因子。在这项工作中，介绍了天然红溴内酯的一系列γ-亚烷基丁烯内酯类似物的脲酶抑制活性。如之前报道的，这些化合物是由商业 3,4-二溴呋喃-(5 H )-2-酮制备的，包括三种新衍生物。rubrolide 类似物（500 µM）的脲酶抑制百分比范围为 20.7% 至 99.3%。最活跃的化合物（IC 50从 111.5 至 306.0 µM）比羟基脲（IC 50844.4 µM)，一种标准脲酶抑制剂。与其他评估的物质相比，具有酚羟基的红溴内酯类似物显示出更高的效力。与一般药代动力学要求相关的理化参数（分配系数、分子量、氢键受体、氢键供体基团数量、可旋转键数量和芳香键数量）显示出所评估的红溴利特类似物的药物样特性。对接研究表明邻位羟基的存在该位置有利于与脲酶形成可逆相互作用，也有利于与活性位点形成共价加合物，从而导致酶的阻断，就像其天然抑制剂儿

  DOI：

  10.1007/s00706-023-03106-y

文献信息

• Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain
  作者：Luiz C. A. Barbosa、Célia R. A. Maltha、Mateus R. Lage、Rosimeire C. Barcelos、Alice Donà、José W. M. Carneiro、Giuseppe Forlani

  DOI：10.1021/jf302921n

  日期：2012.10.24

  used as a model for the development of new drugs and agrochemicals. Following this strategy 11 rubrolide analogues, bearing electron-withdrawing and -donating groups at both benzene rings, were prepared starting from commercially available mucobromic acid. The ability of all compounds to inhibit the photosynthetic electron transport chain in the chloroplast was investigated. The rubrolide analogues

  许多天然产物已被用作开发新药和农用化学品的模型。按照这种策略，从市售的粘溴酸开始制备11个在两个苯环上带有吸电子和给电子基团的rubrolide类似物。研究了所有化合物抑制叶绿体中光合作用电子传输链的能力。rubrolide类似物有效地干扰了光驱动的铁氰化物被分离的叶绿体还原。IC 50实际上，活性最高的衍生物的值仅比具有相同作用方式的商业除草剂（例如Diuron（0.27μM））高1个数量级。QSAR研究表明，最有效的化合物是通过还原过程或亲电反应机理具有更高电子接受能力的化合物。所获得的结果表明，卢布内酯类似物代表了开发靶向光合作用的新活性成分用作除草剂的有前途的候选者。
• Cyclopent-4-ene-1,3-diones: A New Class of Herbicides Acting as Potent Photosynthesis Inhibitors
  作者：Jodieh O. S. Varejão、Luiz C. A. Barbosa、Eduardo V. V. Varejão、Célia R. A. Maltha、Beatriz King-Díaz、Blas Lotina-Hennsen

  DOI：10.1021/jf5014605

  日期：2014.6.25

  In a recent paper, we reported the synthesis and photosynthesis-inhibitory activity of a series of analogues of rubrolides. From quantitative structure-activity relationship (QSAR) studies, we found that the most efficient compounds are those having higher ability to accept electrons. On the basis of those findings, we directed our effort to synthesize new analogues bearing a strong electron-withdrawing group (nitro) in the benzylidene ring and evaluate their effects on photosynthesis. However, the employed synthetic approach led to novel cyclopent-4-ene-1,3-diones as major products. Here, we report the synthesis and mechanism of action of such cyclopent-4-ene-1,3-diones as a new class of photosynthesis inhibitors. These compounds block the electron transport at the QB level by interacting at the D1 protein at the reducing side of Photosystem II and act as Hill reaction inhibitors, with higher activity than the corresponding rubrolides. To the best of our knowledge, this is the first report on the photosynthesis inhibitory activity of cyclopentenediones.
• Rubrolide analogues as urease inhibitors
  作者：Jodieh Oliveira Santana Varejão、Luiz Cláudio Almeida Barbosa、Eduardo Vinícius Vieira Varejão、Nidia Magally Galdámez Coreas、Vinicius Stefano Santos Morais、André Mauricio de Oliveira、Rosimeire Coura Barcelos、Célia Regina Álvares Maltha、Luzia Valentina Modolo

  DOI：10.1007/s00706-023-03106-y

  日期：2023.10

  inhibitor. Rubrolide analogues with phenolic hydroxyl groups revealed higher potency compared with other substances evaluated. Their physicochemical parameters (partition coefficient, molecular weight, hydrogen bonding acceptors, number of hydrogen bonding donor groups, number of rotatable bonds, and the number of aromatic bonds) related to general pharmacokinetic requirements showed drug-like properties

  脲酶是幽门螺杆菌在胃粘膜定植和感染过程中的重要毒力因子。在这项工作中，介绍了天然红溴内酯的一系列γ-亚烷基丁烯内酯类似物的脲酶抑制活性。如之前报道的，这些化合物是由商业 3,4-二溴呋喃-(5 H )-2-酮制备的，包括三种新衍生物。rubrolide 类似物（500 µM）的脲酶抑制百分比范围为 20.7% 至 99.3%。最活跃的化合物（IC 50从 111.5 至 306.0 µM）比羟基脲（IC 50844.4 µM)，一种标准脲酶抑制剂。与其他评估的物质相比，具有酚羟基的红溴内酯类似物显示出更高的效力。与一般药代动力学要求相关的理化参数（分配系数、分子量、氢键受体、氢键供体基团数量、可旋转键数量和芳香键数量）显示出所评估的红溴利特类似物的药物样特性。对接研究表明邻位羟基的存在该位置有利于与脲酶形成可逆相互作用，也有利于与活性位点形成共价加合物，从而导致酶的阻断，就像其天然抑制剂儿