(E)-3-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)acrylic acid | 47174-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)acrylic acid
• 英文别名: 4-(3-oxo-3-phenyl-propenyl)-cinnamic acid；4-(3-Oxo-3-phenyl-propenyl)-zimtsaeure；4-Benzoylvinylenecinnamic acid；(E)-3-[4-[(E)-3-oxo-3-phenylprop-1-enyl]phenyl]prop-2-enoic acid
• CAS: 47174-43-6
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: ZYNOMRYBCZLRSG-DCIPZJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)acrylic acid 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Hydroxyphenylacrylamides and N-Hydroxypyridin-2-ylacrylamides as Novel Histone Deacetylase Inhibitors

  摘要：

  The historic deacetylases (HDACs) are able to regulate gene expression, and historic deacetylase inhibitors (HDACi) emerged as a new class of agents in the treatment of cancer as well as other human disorders such as neurodegenerative diseases. In the present investigation, we report on the synthesis and biological evaluation of compounds derived from the expansion of a HDAC inhibitor scaffold having N-hydroxy-3-phenyl-2-propenamide and N-hydroxy-3-(pyridin-2-yl)-2-propenamide as core structures and containing a phenyloxopropenyl moiety, either unsubstituted or substituted by a 4-methylpiperazin-1-yl or 4-methylpiperazin-1-ylmethyl group. The compounds were evaluated for their ability to inhibit nuclear HDACs, as well as for their in vitro antiproliferative activity. Moreover, their metabolic stability in microsomes and aqueous Solubility were studied and selected compounds were further characterized by in vivo pharmacokinetic experiments. These compounds showed a remarkable stability in vivo, compared to hydroxamic acid HDAC inhibitors that have already entered clinical trials. The representative compound 30b showed in vivo antitumor activity in a human colon carcinoma xenograft model.

  DOI：

  10.1021/jm901502p
• 作为产物：
  描述：

  4-甲酰肉桂酸 、 苯乙酮 在 sodium hydroxide 作用下， 生成 (E)-3-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)acrylic acid
  参考文献：
  名称：

  US2768970

  摘要：

  公开号：

文献信息

• Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls
  作者：Qing Jiang、Jing Jia、Bin Xu、An Zhao、Can-Cheng Guo

  DOI：10.1021/acs.joc.5b00267

  日期：2015.4.3

  The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated

  已经开发出水溶液中α-氧代羧酸与丙烯酸之间的第一个铁促进的脱羧交叉偶联反应。该转化的特征在于其底物范围宽和使用廉价且易于获得的试剂的良好官能团相容性，从而为生物活性化合物中常见的重要一类α，β-不饱和羰基化合物提供了一种有效而快捷的方法。在随后的官能化反应中也证明了偶联产物的合成潜力。初步的机理研究表明，该过程涉及自由基途径：
• CLASS OF HISTONE DEACETYLASE INHIBITORS
  申请人：Mai Antonello

  公开号：US20100113438A1

  公开（公告）日：2010-05-06

  New histone deacetylase inhibitors according to the general formula (I) wherein: Q is a bond, CH 2 , CH—NR 3 R 4 , NR 5 or oxygen, X is CH or nitrogen, Y is a bond, CH 2 , oxygen or NR 6 , Z is CH or nitrogen, R 1 , R 2 are, independently, hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, R 11 , R 12 are, independently, hydrogen or C 1 -C 6 alkyl, and R 3 , R 4 , R 5 and R 6 are as further defined in the specification.

  新的组蛋白去乙酰化酶抑制剂具有以下通式（I）：其中：Q是键，CH2，CH—NR3R4，NR5或氧，X是CH或氮，Y是键，CH2，氧或NR6，Z是CH或氮，R1，R2分别是氢，卤素，C1-C6烷基或C1-C6卤代烷基，R11，R12分别是氢或C1-C6烷基，R3，R4，R5和R6如规范中所进一步定义。
• DE845196
  申请人：——

  公开号：——

  公开（公告）日：——
• US8242175B2
  申请人：——

  公开号：US8242175B2

  公开（公告）日：2012-08-14
• Synthesis and Biological Evaluation of <i>N</i>-Hydroxyphenylacrylamides and <i>N</i>-Hydroxypyridin-2-ylacrylamides as Novel Histone Deacetylase Inhibitors
  作者：Florian Thaler、Andrea Colombo、Antonello Mai、Raffaella Amici、Chiara Bigogno、Roberto Boggio、Anna Cappa、Simone Carrara、Tiziana Cataudella、Fulvia Fusar、Eleonora Gianti、Samuele Joppolo di Ventimiglia、Maurizio Moroni、Davide Munari、Gilles Pain、Nickolas Regalia、Luca Sartori、Stefania Vultaggio、Giulio Dondio、Stefania Gagliardi、Saverio Minucci、Ciro Mercurio、Mario Varasi

  DOI：10.1021/jm901502p

  日期：2010.1.28

  The historic deacetylases (HDACs) are able to regulate gene expression, and historic deacetylase inhibitors (HDACi) emerged as a new class of agents in the treatment of cancer as well as other human disorders such as neurodegenerative diseases. In the present investigation, we report on the synthesis and biological evaluation of compounds derived from the expansion of a HDAC inhibitor scaffold having N-hydroxy-3-phenyl-2-propenamide and N-hydroxy-3-(pyridin-2-yl)-2-propenamide as core structures and containing a phenyloxopropenyl moiety, either unsubstituted or substituted by a 4-methylpiperazin-1-yl or 4-methylpiperazin-1-ylmethyl group. The compounds were evaluated for their ability to inhibit nuclear HDACs, as well as for their in vitro antiproliferative activity. Moreover, their metabolic stability in microsomes and aqueous Solubility were studied and selected compounds were further characterized by in vivo pharmacokinetic experiments. These compounds showed a remarkable stability in vivo, compared to hydroxamic acid HDAC inhibitors that have already entered clinical trials. The representative compound 30b showed in vivo antitumor activity in a human colon carcinoma xenograft model.