2-cyano-N-[2-(ethoxy)phenyl]acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-N-[2-(ethoxy)phenyl]acetamide
• 英文别名: N-(o-ethoxyphenyl)cyanoacetanilide；N-[2-ethoxyphenyl]cyanoacetamide；cyano-acetic acid o-phenetidide；Cyan-essigsaeure-o-phenetidid；2-cyano-N-(2-ethoxyphenyl)acetamide
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD03150623
• 分子量: 204.228
• InChiKey: XMENNTQSJXXKKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-N-[2-(ethoxy)phenyl]acetamide 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以59%的产率得到3-amino-3-(hydroxyimino)-N-[2-(ethoxy)phenyl]propanamide
  参考文献：
  名称：

  Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

  摘要：

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.

  DOI：

  10.1021/jm3002845
• 作为产物：
  描述：

  氰乙酸 、 氨基苯乙醚 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以81%的产率得到2-cyano-N-[2-(ethoxy)phenyl]acetamide
  参考文献：
  名称：

  Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

  摘要：

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.

  DOI：

  10.1021/jm3002845

文献信息

• Synthesis, characterization, and evaluation of some novel 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents
  作者：Awatef A. Farag、Ebtsam M. Khalifa、Naima A. Sadik、Samir Y. Abbas、Abdullah G. Al-Sehemi、Yousry A. Ammar

  DOI：10.1007/s00044-012-0046-6

  日期：2013.1

  3-(4-chlorophenyl or 4-fluorophenyl)-6-iodo-4-oxo-3,4-dihydroquinazoline derivatives having a Schiff bases, oxazolone, imidazolidine, pyrazolidine, pyridine, pyrimidine, and various substituted C-2 have been synthesized. Screening for some selected compounds was carried out for their potential anti-inflammatory and analgesic activity.

  一些新的3-（4-氯苯基或4-氟苯基）-6-碘-4-氧代-3,4-二氢喹唑啉衍生物，具有席夫碱，恶唑酮，咪唑烷，吡唑烷，吡啶，嘧啶和各种取代的C-2已经合成。筛选一些选定的化合物的潜在抗炎和止痛活性。
• Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors
  作者：Woldeamanuel Birru、Ross T. Fernley、Lloyd D. Graham、Julian Grusovin、Ronald J. Hill、Albert Hofmann、Linda Howell、Peter J. James、Karen E. Jarvis、Wynona M. Johnson、Dionne A. Jones、Christa Leitner、Andris J. Liepa、George O. Lovrecz、Louis Lu、Roland H. Nearn、Brian J. O’Driscoll、Tram Phan、Matthew Pollard、Kathleen A. Turner、David A. Winkler

  DOI：10.1016/j.bmc.2010.06.020

  日期：2010.8

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Desai, Journal of the Indian Chemical Society, 1955, vol. 32, p. 592
  作者：Desai

  DOI：——

  日期：——
• One step synthesis of 1,5-diaryl pyridin-2(1H)-ones from 2-aryl vinamidinium salts and N-aryl cyanoacetamides
  作者：Jiabin Yang、Guoqiang Su、Yu Ren、Yang Chen

  DOI：10.1016/j.tet.2014.09.041

  日期：2014.11

  A one step, direct method for the synthesis of 1,5-diaryl pyridin-2(1H)-one derivatives by condensation of 2-aryl vinamidinium salts with N-aryl cyanoacetamides has been developed. This method can conveniently provide the corresponding 1,5-diaryl pyridin-2(1H)-one derivatives with various substituents in good yields and overcome the drawbacks of existing methods such as poor substrate scope, heavy metal pollution, and low yields. The formation mechanism of the products was illustrated. (C) 2014 Elsevier Ltd. All rights reserved.
• Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1
  作者：Stuart Hazeldine、Boobalan Pachaiyappan、Nora Steinbergs、Shannon Nowotarski、Allison S. Hanson、Robert A. Casero、Patrick M. Woster

  DOI：10.1021/jm3002845

  日期：2012.9.13

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.