ethyl 3-(4-butylphenyl)-3-oxopropanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-butylphenyl)-3-oxopropanoate
• 英文别名: Ethyl 3-(4-butylphenyl)-3-oxopropanoate
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: MUWDHLCSXAAXFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-butylphenyl)-3-oxopropanoate 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 5-(4-butylphenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360
• 作为产物：
  描述：

  4-丁基苯甲酸 在 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 ethyl 3-(4-butylphenyl)-3-oxopropanoate
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360

文献信息

• Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization
  作者：Mrinal K. Bera、Rumpa Sarkar、Surya Kanta Samanta、Anila M. Menon、Deepak Chopra、Debabani Ganguly

  DOI：10.1055/a-2116-5206

  日期：2023.10

  diversely substituted quinoline and quinolin-2-one derivatives is disclosed. In situ generated nickel boride proved to be an effective promoter of the reductive cyclization reaction. Broad substrate scope, mild reaction conditions, consistent yield, and a wide range of functional group tolerance are the other notable features of the newly discovered reaction. A large number of quinoline and quinolin-2-one

  公开了一种温和且有效的合成不同取代的喹啉和喹啉-2-酮衍生物的方法。原位生成的硼化镍被证明是还原环化反应的有效促进剂。广泛的底物范围、温和的反应条件、稳定的产率和广泛的官能团耐受性是新发现的反应的其他显着特征。采用这种分子内还原环化方案，可以制备毫克至多克规模的大量喹啉和喹啉-2-酮衍生物。
• Tetramate derivatives by chemoselective Dieckmann ring closure of<i>allo</i>-phenylserines, and their antibacterial activity
  作者：Liban Saney、Kirsten E. Christensen、Miroslav Genov、Alexander Pretsch、Dagmar Pretsch、Mark G. Moloney

  DOI：10.1039/d3ob00376k

  日期：——

  showing the importance of steric bulk around the bicyclic ring system. The derived C7-carboxamidotetramates, but not C7-acyl systems, exhibited potent antibacterial activity against MRSA, with the most active compounds exhibiting well-defined physicochemical and structure–activity properties. This work clearly demonstrates that densely functionalised tetramates are both readily available and may exhibit

  报道了一种通用途径，该途径利用衍生自别苯丝氨酸的恶唑烷衍生物的 Dieckmann 环化作用，可直接获得取代的双环四酸酯。有趣的是观察到恶唑烷的N-酰化反应的高水平非对映选择性及其在 Dieckmann 环化中闭环的完全化学选择性。重要的是，化学选择性的意义与早先报道的threo不同-苯丝氨酸系统，显示了双环系统周围空间体积的重要性。衍生的 C7-甲酰胺四甲酸酯，但不是 C7-酰基系统，对 MRSA 表现出强大的抗菌活性，其中最活跃的化合物表现出明确的物理化学和结构-活性特性。这项工作清楚地表明，密集功能化的四聚体既容易获得，又可能表现出高水平的抗菌活性。