ethyl (E)-3-(5-formylfuran-2-yl)acrylate | 191480-39-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3-(5-formylfuran-2-yl)acrylate
• 英文别名: 3-(5-Formyl-furan-2-yl)-acrylic acid ethyl ester；ethyl (E)-3-(5-formylfuran-2-yl)prop-2-enoate
• CAS: 191480-39-4
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: JFHDAHZVHSOCLB-AATRIKPKSA-N

物化性质

• 熔点：
  73.4-74 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  330.3±32.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(5-formylfuran-2-yl)acrylate 在 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 11.5h， 生成 (E)-ethyl 3-{5-{[benzyl(butyl)amino]methyl}furan-2-yl}acrylate
  参考文献：
  名称：

  Novel N-hydroxyfurylacrylamide-based histone deacetylase (HDAC) inhibitors with branched CAP group (Part 2)

  摘要：

  Histone deacetylases (HDACs) are significant enzymes involved in tumor genesis and development. Herein, we report a series of novel N-hydroxyfurylacryl-amide-based HDAC inhibitors, which are marked by introducing branched hydrophobic groups as the capping group. The inhibitory activity of the synthesized compounds against HDACs and several tumor cell lines are firstly determined. Fifteen compounds with promising activities are selected for further evaluation of target selectivity profile against recombinant human HDAC1, HDAC4 and HDAC6. Compounds 10a, 10b, 10d and 16a exhibit outstanding selectivity against HDAC6. Analysis of HDAC4 X-ray structure and HDAC1, HDAC6 homology model indicates that these enzyme differ significantly in the rim near the surface of the active site. Although TSA has been known as a pan-HDAC inhibitor, it exhibits outstanding selectivity for HDAC6 over HDAC4. For further physicochemical properties study, six compounds are chosen for determination of their physicochemical properties including logD(7.4) and aqueous solubility. The results suggest that compounds with a smaller framework and with hydrophilicgroups are likely to have better aqueous solubility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.009
• 作为产物：
  描述：

  ethyl (2E)-3-(furan-2-yl)acrylate 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 反应 2.33h， 以82.5%的产率得到ethyl (E)-3-(5-formylfuran-2-yl)acrylate
  参考文献：
  名称：

  Novel N-hydroxyfurylacrylamide-based histone deacetylase (HDAC) inhibitors with branched CAP group (Part 2)

  摘要：

  Histone deacetylases (HDACs) are significant enzymes involved in tumor genesis and development. Herein, we report a series of novel N-hydroxyfurylacryl-amide-based HDAC inhibitors, which are marked by introducing branched hydrophobic groups as the capping group. The inhibitory activity of the synthesized compounds against HDACs and several tumor cell lines are firstly determined. Fifteen compounds with promising activities are selected for further evaluation of target selectivity profile against recombinant human HDAC1, HDAC4 and HDAC6. Compounds 10a, 10b, 10d and 16a exhibit outstanding selectivity against HDAC6. Analysis of HDAC4 X-ray structure and HDAC1, HDAC6 homology model indicates that these enzyme differ significantly in the rim near the surface of the active site. Although TSA has been known as a pan-HDAC inhibitor, it exhibits outstanding selectivity for HDAC6 over HDAC4. For further physicochemical properties study, six compounds are chosen for determination of their physicochemical properties including logD(7.4) and aqueous solubility. The results suggest that compounds with a smaller framework and with hydrophilicgroups are likely to have better aqueous solubility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.009

文献信息

• Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
  作者：Argha Saha、Srimanta Guin、Wajid Ali、Trisha Bhattacharya、Sheuli Sasmal、Nupur Goswami、Gaurav Prakash、Soumya Kumar Sinha、Hediyala B. Chandrashekar、Sanjib Panda、S. S. Anjana、Debabrata Maiti

  DOI：10.1021/jacs.1c12311

  日期：2022.2.2

  regioselectivity. Often, the high thermal energy required to promote olefination leads to multiple site functionalizations. To this aim, we established a photoredox catalytic system constituting a merger of palladium/organo-photocatalyst (PC) that forges oxidative olefination in an explicit regioselective fashion with diverse arenes and heteroarenes. Visible light plays a significant role in executing “regioresolved”

  藤原-森谷反应对当代 C-H 激活方案的出现做出了深远的贡献。尽管传统方法在不同领域具有适用性，但相关的反应性和区域选择性问题使其变得多余。该示例性反应的复兴需要开发一种机械范式，该范式将同时控制反应性和区域选择性。通常，促进烯烃化所需的高热能导致多位点官能化。为此，我们建立了一个光氧化还原催化系统，该系统由钯/有机光催化剂 (PC) 的合并组成，该系统以显式的区域选择性方式与多种芳烃和杂芳烃进行氧化烯化。可见光在不需要银盐和热能的情况下在执行“区域分解”的藤原-森谷反应中起着重要作用。该催化系统还可以在各自的导向基团 (DGs) 的帮助下进行近端和远端烯烃化，这需要该协议在参与整个 C(sp) 光谱方面的多功能性2 )-H烯化。此外，通过后期功能化简化天然产物、手性分子、药物的合成和多样化，强调了这种可持续协议的重要性。这种区域选择性转化的光诱导实现是通过控制反应和动力学研究机械地建立的。
• Evaluation of pyrrolin-2-one derivatives synthesized by a new practical method as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  作者：Hiroshi Miyazaki、Tsutomu Miyake、Yoshihiro Terakawa、Hiroshi Ohmizu、Tsuyoshi Ogiku、Akio Ohtani

  DOI：10.1016/j.bmcl.2009.11.102

  日期：2010.1

  We describe in this Letter a new synthetic method for pyrrolin-2-ones as potent plasminogen activator inhibitor-1 (PAI-1) inhibitors. Pyrrolin-2-one derivatives synthesized from N-2-oxoethylamides and aldehydes in aqueous NaOH by one-pot were evaluated for their PAI-1 inhibitory activity. Among these derivatives, compounds 16 and 18 were found to possess potent PAI-1 inhibitory activity (compound 16:

  我们在这封信中描述了吡咯啉-2-酮作为有效的纤溶酶原激活物抑制剂1（PAI-1）抑制剂的一种新的合成方法。评价了由一锅法在NaOH水溶液中由N -2-氧乙基酰胺和醛合成的吡咯啉-2-一衍生物的PAI-1抑制活性。在这些衍生物中，发现化合物16和18具有有效的PAI-1抑制活性（化合物16：IC 50：0.69μM，化合物18：IC 50：0.65μM）。
• Correction to “Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites”
  作者：Argha Saha、Srimanta Guin、Wajid Ali、Trisha Bhattacharya、Sheuli Sasmal、Nupur Goswami、Gaurav Prakash、Soumya Kumar Sinha、Hediyala B. Chandrashekar、Sanjib Panda、S. S. Anjana、Debabrata Maiti

  DOI：10.1021/jacs.2c04257

  日期：2022.5.25

  Supporting Information. The authors wish to correct an inadvertent error in connection with the spectra provided for compound 36. The revised Supporting Information is included with this correction. The revised data does not alter the conclusions of the published work. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c04257. Experimental procedures and

  支持信息。作者希望纠正与为化合物36提供的光谱有关的无意错误。修订后的支持信息包含在此更正中。修改后的数据不会改变已发表作品的结论。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c04257 免费获得。实验程序和分析数据 ( 1 H, 13C NMR、MS、HPLC）（已更正）（PDF）大多数电子支持信息文件无需订阅 ACS 网络版即可获得。此类文件可以按文章下载以供研究使用（如果有与相关文章链接的公共使用许可，则该许可可能允许其他用途）。可通过 RightsLink 许可系统请求从 ACS 获得其他用途的许可：http://pubs.acs.org/page/copyright/permissions.html。这篇文章尚未被其他出版物引用。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c04257
• Design, synthesis and biological evaluation of novel compounds with conjugated structure as anti-tumor agents
  作者：Hong Su、Angela Nebbioso、Vincenzo Carafa、Yadong Chen、Bo Yang、Lucia Altucci、Qidong You

  DOI：10.1016/j.bmc.2008.07.066

  日期：2008.9

  A series of hydroxamic acids with conjugated structure was designed and synthesized to explore the possible HDAC subtype selectivity by testing these compounds against recombinant human HDAC1 and HDAC4. The most selective compound resulted 5a, with a SI of 11.9. The enzymatic inhibitory activity of these conjugated compounds was relatively weak; however, some of these compounds showed significant effect in inducing apoptosis. Moreover, the anti-proliferative activity in cancer cells resulted quite promising, especially in the HCT119 cell line. (C) 2008 Elsevier Ltd. All rights reserved.
• Novel N-hydroxyfurylacrylamide-based histone deacetylase (HDAC) inhibitors with branched CAP group (Part 2)
  作者：Taotao Feng、Hai Wang、Hong Su、Hui Lu、Liqin Yu、Xiaojin Zhang、Haopeng Sun、Qidong You

  DOI：10.1016/j.bmc.2013.06.009

  日期：2013.9

  Histone deacetylases (HDACs) are significant enzymes involved in tumor genesis and development. Herein, we report a series of novel N-hydroxyfurylacryl-amide-based HDAC inhibitors, which are marked by introducing branched hydrophobic groups as the capping group. The inhibitory activity of the synthesized compounds against HDACs and several tumor cell lines are firstly determined. Fifteen compounds with promising activities are selected for further evaluation of target selectivity profile against recombinant human HDAC1, HDAC4 and HDAC6. Compounds 10a, 10b, 10d and 16a exhibit outstanding selectivity against HDAC6. Analysis of HDAC4 X-ray structure and HDAC1, HDAC6 homology model indicates that these enzyme differ significantly in the rim near the surface of the active site. Although TSA has been known as a pan-HDAC inhibitor, it exhibits outstanding selectivity for HDAC6 over HDAC4. For further physicochemical properties study, six compounds are chosen for determination of their physicochemical properties including logD(7.4) and aqueous solubility. The results suggest that compounds with a smaller framework and with hydrophilicgroups are likely to have better aqueous solubility. (C) 2013 Elsevier Ltd. All rights reserved.