ethyl 3-oxo-3-(4-propoxyphenyl)propanoate | 932042-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-oxo-3-(4-propoxyphenyl)propanoate
• 英文别名: Ethyl 3-oxo-3-(4-propoxyphenyl)propionate
• CAS: 932042-48-3
• 化学式: C₁₄H₁₈O₄
• mdl: MFCD11542256
• 分子量: 250.295
• InChiKey: CAPHAWCDQKHCAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-oxo-3-(4-propoxyphenyl)propanoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.75h， 以88%的产率得到3-(4-propoxyphenyl)-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Synthesis of new mesogens of the 3-arylisoxazolone and 3-arylpyrazolone series

  摘要：

  Acylation of ethyl acetoacetate with mesogenic para-substituted benzoyl chlorides, followed by cleavage of ethyl aroylacetoacetates thus obtained under basic conditions, gave the corresponding ethyl 3-aryl-3-oxopropanoates which were brought into condensations with hydroxylamine and hydrazine to obtain mesogenic 3-arylisoxazolones and 3-arylpyrazolones, respectively.

  DOI：

  10.1134/s1070428010120067
• 作为产物：
  描述：

  4-丙氧基苯甲酸 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-oxo-3-(4-propoxyphenyl)propanoate
  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

• A Quantitative Structure−Activity Relationship Study of Herbicidal Analogues of α-Hydroxy-Substituted 3-Benzylidenepyrrolidene-2,4-diones
  作者：You-quan Zhu、Pei Liu、Xue-Kai Si、Xiao-Mao Zou、Bin Liu、Hai-Bin Song、Hua-zheng Yang

  DOI：10.1021/jf061573j

  日期：2006.9.1

  A series of pyrrolidine-2,4-dione and piperidine-2,4-dione derivatives were prepared and evaluated for their herbicidal activities where some of these compounds exhibited good bioactivity against Echinochloa crus-galli in comparison with sulcotrione. Quantitative structure- activity relationship studies were performed on these compounds using physicochemical parameters ( hydrophobic, electronic, and Taft) as independent parameters and herbicidal activity as a dependent parameter, where herbicidal activity correlated best (r > 0.8) with hydrophobic (pi degrees + pi(p)), steric (Es), STERIMOL (B4), indicator (H-M), van der Waals volume (V), and electronic parameter (sigma(m) + sigma(p)) in this set of molecules; the optimum van der Waals volume for R-2 is about 41.8 A(3); when B4 is equal to 3, the target molecule possessed the lowest herbicidal activity.
• Pyrrolidine-3-carboxylic Acids as Endothelin Antagonists. 2. Sulfonamide-Based ET_A/ET_B Mixed Antagonists
  作者：Hwan-Soo Jae、Martin Winn、Douglas B. Dixon、Kennan C. Marsh、Bach Nguyen、Terry J. Opgenorth、Thomas W. von Geldern

  DOI：10.1021/jm970101g

  日期：1997.9.1

  When the N,N-dialkylacetamide side chain of the highly ETA-selective endothelin antagonist ABT-627 (1; [2R,3R,4S]-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1-[[(N,N-dibutylamino)carbonyl]methyl]pyrrolidine-3-carboxylic acid; A-147627) is replaced by N,S-dialkylsulfonamidoethyl, the resultant analogs retain ETA affinity, but exhibit substantial ETB affinity as well. Structure-activity studies reveal that modifications in the length of the two alkyl groups, and in the substitution on the anisyl ring, are important in optimizing this ''balanced'' antagonist profile. In particular the combination of an N-n-propyl group, an S-alkyl chain between four and six carbons in length, and a fluorine atom ortho to the aromatic OCH3 provides compounds with sub-nanomolar affinities for both receptor subtypes, and with ETA/ETB ratios close to 1. A number of these compounds also exhibit oral bioavailabilities (in rats) in the 30-50% range and have substantial plasma half-lives. The balanced receptor-binding profile of these potent and orally bioavailable compounds complements the ETA selectivity observed with 1.
• 2-Phenylquinoline <i>S. aureus</i> NorA Efflux Pump Inhibitors: Evaluation of the Importance of Methoxy Group Introduction
  作者：Tommaso Felicetti、Rolando Cannalire、Donatella Pietrella、Gniewomir Latacz、Annamaria Lubelska、Giuseppe Manfroni、Maria Letizia Barreca、Serena Massari、Oriana Tabarrini、Katarzyna Kieć-Kononowicz、Bryan D. Schindler、Glenn W. Kaatz、Violetta Cecchetti、Stefano Sabatini

  DOI：10.1021/acs.jmedchem.8b00791

  日期：2018.9.13

  Antimicrobial resistance (AMR) represents a hot topic in drug discovery. Besides the identification of new antibiotics, the use of nonantibiotic molecules to block resistance mechanisms is a powerful alternative. Bacterial efflux pumps exert an early step in AMR development by allowing bacteria to grow at subinhibitorial drug concentrations. Thus, efflux pump inhibitors (EPIs) offer a great opportunity to fight AMR Given our experience in developing Staphylococcus aureus NorA EPIs, in this work, starting from the 2-phenylquinoline hit 1, we planned the introduction of methoxy groups on the basis of their presence in known NorA EPIs. Among the 35 different synthesized derivatives, compounds 3b and 7d exhibited the best NorA inhibition activity by restoring at very low concentrations ciprofloxacin MICs against resistant S. aureus strains. Interestingly, both compounds displayed EPI activities at nontoxic concentrations for human cells as well as highlighted promising results by preliminary pharmacokinetic studies.
• New C-6 functionalized quinoline NorA inhibitors strongly synergize with ciprofloxacin against planktonic and biofilm growing resistant Staphylococcus aureus strains
  作者：Tommaso Felicetti、Nicholas Cedraro、Andrea Astolfi、Giada Cernicchi、Gianmarco Mangiaterra、Salvatore Vaiasicca、Serena Massari、Giuseppe Manfroni、Maria Letizia Barreca、Oriana Tabarrini、Francesca Biavasco、Violetta Cecchetti、Carla Vignaroli、Stefano Sabatini

  DOI：10.1016/j.ejmech.2022.114656

  日期：2022.11
• Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
  作者：Zi-Long Song、Feifei Bai、Baoxin Zhang、Jianguo Fang

  DOI：10.1021/acs.jafc.9b06360

  日期：2020.2.19

  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.