N-[2-(4-nitrophenyl)ethyl]prop-2-en-1-amine | 1153484-59-3

• 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: N-[2-(4-nitrophenyl)ethyl]prop-2-en-1-amine
• CAS: 1153484-59-3
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: VIAJHPUCFRLCGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(4-nitrophenyl)ethyl]prop-2-en-1-amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-{1-[2-(4-nitro-phenyl)-ethyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-propionic acid methyl ester
  参考文献：
  名称：

  Property-Based Optimization of Hydroxamate-Based γ-Lactam HDAC Inhibitors to Improve Their Metabolic Stability and Pharmacokinetic Profiles

  摘要：

  Hydroxamate-based HDAC inhibitors have promising anticancer activities but metabolic instability and poor pharmacokinetics leading to poor in vivo results. QSAR and PK studies of HDAC inhibitors showed that a gamma-lactam core and a modified cap group, including halo, alkyl, and alkoxy groups with various carbon chain linkers, improved HDAC inhibition and metabolic stability. The biological properties of the gamma-lactam HDAC inhibitors were evaluated; the compound designated 8f had potent anticancer activity and high oral bioavailability.

  DOI：

  10.1021/jm3009376

文献信息

• Lactam-Based HDAC Inhibitors for Anticancer Chemotherapy: Restoration of RUNX3 by Posttranslational Modification and Epigenetic Control
  作者：Misun Cho、Eunhyun Choi、Jae Hyun Kim、Hwan Kim、Hwan Mook Kim、Jang Ik Lee、Ki-Chul Hwang、Hyun-Jung Kim、Gyoonhee Han

  DOI：10.1002/cmdc.201300393

  日期：2014.3

  transcription factor 3 (RUNX3) are regulated by histone deacetylase (HDAC). HDAC inhibition alters epigenetic and posttranslational stability of RUNX3, leading to tumor suppression. However, HDAC inhibitors can nonselectively alter global gene expression through chromatin remodeling. Thus, lactam‐based HDAC inhibitors were screened to identify potent protein stabilizers that maintain RUNX3 stability by acetylation

  肿瘤抑制子相关转录因子3（RUNX3）的表达和稳定性受组蛋白脱乙酰基酶（HDAC）调节。HDAC抑制会改变RUNX3的表观遗传和翻译后稳定性，从而导致肿瘤抑制。但是，HDAC抑制剂可以通过染色质重塑非选择性地改变全局基因的表达。因此，筛选了基于内酰胺的HDAC抑制剂以鉴定有效的蛋白质稳定剂，该稳定剂可通过乙酰化保持RUNX3的稳定性。通过基于细胞的RUNX激活和HDAC抑制测定法确定了111种基于内酰胺的类似物的RUNX活性和HDAC抑制作用。3- [1-（4-溴苄基）-2-氧代-2,5-二氢-1 H-吡咯-3-基] -N-羟基丙酰胺（11-8）可显着提高RUNX3的乙酰化和稳定性，并具有相对较低的RUNX3 mRNA表达和HDAC抑制活性。在MKN28异种移植模型中，该化合物显示出显着的抗肿瘤作用，比SAHA强。因此，我们提出了一种新的策略，其中HDAC抑制剂用作选择性靶向RUNX3的表
• Material exhibiting compensation for polymerization-induced shrinkage and recording medium formed therefrom
  申请人：LUCENT TECHNOLOGIES INC.

  公开号：EP0969323A1

  公开（公告）日：2000-01-05

  The invention relates to use of a material containing a polymerizable monomer or oligomer, the material exhibiting desirable shrinkage compensation upon polymerization. The material contains an expansion agent having a cleaving moiety with the capacity to be cleaved or fragmented by a catalytic reaction, e.g., acid catalysis. The cleavage, by increasing the number of molecules in the material, causes expansion that compensates, at least in part, for shrinkage induced by polymerization of the monomer or oligomer. The expansion agent is capable of providing compensation such that no more than 0.4%, advantageously no more than 0.2 %, volume shrinkage per molar concentration of polymerized monomer functional groups occurs, where such compensation is performed at relatively low temperatures of less than 40°C.

  本发明涉及一种含有可聚合单体或低聚物的材料的用途，这种材料在聚合时会表现出理想的收缩补偿。该材料含有一种膨胀剂，该膨胀剂具有裂解分子，可通过催化反应（如酸催化）裂解或破碎。通过增加材料中分子的数量，裂解可导致膨胀，至少部分补偿单体或低聚物聚合引起的收缩。膨胀剂能够提供补偿，使每摩尔浓度的聚合单体官能团的体积收缩率不超过 0.4%，最好不超过 0.2%，而这种补偿是在低于 40°C 的相对低温下进行的。
• US6124076A
  申请人：——

  公开号：US6124076A

  公开（公告）日：2000-09-26
• US6221536B1
  申请人：——

  公开号：US6221536B1

  公开（公告）日：2001-04-24
• Property-Based Optimization of Hydroxamate-Based γ-Lactam HDAC Inhibitors to Improve Their Metabolic Stability and Pharmacokinetic Profiles
  作者：Eunhyun Choi、Chulho Lee、Misun Cho、Jeong Jea Seo、Jee Sun Yang、Soo Jin Oh、Kiho Lee、Song-Kyu Park、Hwan Mook Kim、Ho Jeong Kwon、Gyoonhee Han

  DOI：10.1021/jm3009376

  日期：2012.12.13

  Hydroxamate-based HDAC inhibitors have promising anticancer activities but metabolic instability and poor pharmacokinetics leading to poor in vivo results. QSAR and PK studies of HDAC inhibitors showed that a gamma-lactam core and a modified cap group, including halo, alkyl, and alkoxy groups with various carbon chain linkers, improved HDAC inhibition and metabolic stability. The biological properties of the gamma-lactam HDAC inhibitors were evaluated; the compound designated 8f had potent anticancer activity and high oral bioavailability.