(E)-3-(pyridin-4-yl)-N-hydroxyacrylamide | 1204230-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-3-(pyridin-4-yl)-N-hydroxyacrylamide
• 英文别名: (E)-N-hydroxy-3-(pyridin-4-yl)acrylamide；(E)-3-(4-pyridyl)prop-2-enehydroxamic acid；(E)-N-hydroxy-3-pyridin-4-ylprop-2-enamide
• CAS: 1204230-66-9
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: FHKODKLQSIWYMG-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (E)-3-(4-pyridyl)propenoate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到(E)-3-(pyridin-4-yl)-N-hydroxyacrylamide
  参考文献：
  名称：

  N-羟基肉桂酰胺类似物的鉴定及其对乳腺癌细胞系的生物评价。

  摘要：

  本研究证明了N-羟基肉桂酰胺衍生物的鉴定及其对人三阴性乳腺癌细胞MDA-MB‑231，MCF-7和非恶性起源细胞系HEK-293（人胚胎肾脏）的抗癌潜力。用HEK-293细胞系研究MTT测定。通过体外研究，将N-羟基肉桂酰胺衍生物的抗癌潜力与标记的药物他莫昔芬进行了比较。化合物编号3b和3h分别对IC5013μM和5μM的拮抗性乳腺癌细胞（MDA-MB-231）表现出最强的活性。化合物3h促进DNA片段化并诱导凋亡。此外，化合物3h引起线粒体膜电位的损失。

  DOI：

  10.1016/j.biopha.2018.08.015

文献信息

• Design, synthesis and antibacterial activity against pathogenic mycobacteria of conjugated hydroxamic acids, hydrazides and O-alkyl/O-acyl protected hydroxamic derivatives
  作者：Vasiliki Mavrikaki、Alexandros Pagonis、Isabelle Poncin、Ivy Mallick、Stéphane Canaan、Victoria Magrioti、Jean-François Cavalier

  DOI：10.1016/j.bmcl.2022.128692

  日期：2022.5

  their toxicity towards murine macrophages by the resazurin microtiter assay (REMA). Among the 45 derivatives, 17 compounds (3 hydroxamic acids, 9 hydrazides, and 5O-alkyl/O-acyl protected hydroxamic acids) were nontoxic against murine macrophages. When tested for their antibacterial activity, hydroxamic acid 9 h was found to be the most potent inhibitor against M. abscessus S and R only. Regarding hydrazide

  以发现新的抗结核分子为目的，合成了三个新系列的 23 异羟肟酸、13 酰肼和 9O-烷基/O-酰基保护异羟肟酸衍生物，并通过光谱1 H NMR、13 C NMR、HRMS对其进行了全面表征。 ） 分析。通过刃天青微量滴定法 (REMA) 进一步对这些化合物进行了生物筛选，以了解它们对三种致病性分枝杆菌（脓肿分枝杆菌 S 和 R、海分枝杆菌和结核分枝杆菌）的体外抗菌活性，以及​​它们对小鼠巨噬细胞的毒性。 . 在 45 种衍生物中，17 种化合物（3 种异羟肟酸、9 种酰肼和 5O-烷基/O-酰基保护的异羟肟酸）对小鼠巨噬细胞无毒。当测试它们的抗菌活性时，异羟肟酸发现9 小时仅对脓肿分枝杆菌 S 和 R 是最有效的抑制剂。酰肼系列对脓肿分枝杆菌R、海分枝杆菌和结核分枝杆菌的活性仅7h ；而 O- 酰基保护的异羟肟酸衍生物14d和15d对 M. marinum 和 M. tuberculosis
• 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.
• Identification of N-Hydroxycinnamamide analogues and their bio-evaluation against breast cancer cell lines
  作者：Akhilesh Kumar Shukla、Hamidullah、Manoj Kumar Shrivash、Vishwa Deepak Tripathi、Rituraj Konwar、Jyoti Pandey

  DOI：10.1016/j.biopha.2018.08.015

  日期：2018.11

  exhibit most potent activity against antagonistic breast cancer cells (MDA-MB-231) with IC5013μM and 5μM respectively. Compound 3h promotes DNA fragmentation and induction of apoptosis. Furthermore, loss of mitochondrial membrane potential induced by compound 3h. The major mechanism of compound 3h for anti-breast cancer activity was probably initiation of reactive oxygen species (ROS) in cancer cells thereby

  本研究证明了N-羟基肉桂酰胺衍生物的鉴定及其对人三阴性乳腺癌细胞MDA-MB‑231，MCF-7和非恶性起源细胞系HEK-293（人胚胎肾脏）的抗癌潜力。用HEK-293细胞系研究MTT测定。通过体外研究，将N-羟基肉桂酰胺衍生物的抗癌潜力与标记的药物他莫昔芬进行了比较。化合物编号3b和3h分别对IC5013μM和5μM的拮抗性乳腺癌细胞（MDA-MB-231）表现出最强的活性。化合物3h促进DNA片段化并诱导凋亡。此外，化合物3h引起线粒体膜电位的损失。