4-Nitro-3'-chlor-stilben | 51751-39-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-Nitro-3'-chlor-stilben
• 英文别名: 1-Chloro-3-[2-(4-nitrophenyl)ethenyl]benzene
• CAS: 51751-39-4
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: REQIUGALNFLDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Nitro-3'-chlor-stilben 在 盐酸 、 铁粉 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (Z)-1-(4-(3-chlorostyryl)phenyl)-3-ethylurea
  参考文献：
  名称：

  Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model

  摘要：

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.034
• 作为产物：
  描述：

  对硝基溴化苄 在 sodium hydride 、 3-氯苯甲醛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 4-Nitro-3'-chlor-stilben
  参考文献：
  名称：

  Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model

  摘要：

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.034

文献信息

• The synthesis and structure–activity relationship of substituted N-phenyl anthranilic acid analogs as amyloid aggregation inhibitors
  作者：Lloyd J. Simons、Bradley W. Caprathe、Michael Callahan、James M. Graham、Takenori Kimura、Yingjie Lai、Harry LeVine、William Lipinski、Annette T. Sakkab、Yoshikazu Tasaki、Lary C. Walker、Tomoyuki Yasunaga、Yuyang Ye、Nian Zhuang、Corinne E. Augelli-Szafran

  DOI：10.1016/j.bmcl.2008.12.049

  日期：2009.2

  Alzheimer’s disease. In the course of our studies to identify β-amyloid aggregation inhibitors, a series of N-phenyl anthranilic acid analogs were synthesized and studied for β-amyloid inhibition activity. The synthesis, structure–activity relationship, and in vivo activity of these analogs are discussed.

  认为β-淀粉样蛋白聚集是阿尔茨海默氏病发展中的重要事件。在我们鉴定β-淀粉样蛋白聚集抑制剂的研究过程中，合成了一系列N-苯基邻氨基苯甲酸类似物，并研究了β-淀粉样蛋白抑制活性。讨论了这些类似物的合成，结构-活性关系以及体内活性。
• 4-pyrrolidino-phenyl-benzyl ether derivatives
  申请人：Iding Hans

  公开号：US20060122235A1

  公开（公告）日：2006-06-08

  The invention relates to racemic or enantiomerically pure 4-pyrrolidino derivatives, processes for their preparation, pharmaceutical compositions comprising said derivatives, and their use in the prevention and treatment of illness, in particular which is mediated by monoamine oxidase B inhibitors, in particular Alzheimer's disease or senile dementia.

  本发明涉及外消旋或对映纯的4-吡咯烷基衍生物，其制备方法，包含该衍生物的制药组合物，以及其在预防和治疗疾病中的应用，特别是在通过单胺氧化酶B抑制剂介导的疾病中，特别是阿尔茨海默病或老年性痴呆症的应用。
• 4-Pyrrolidino-phenyl-benzyl ether derivatives
  申请人：——

  公开号：US20040106650A1

  公开（公告）日：2004-06-03

  The invention relates to racemic or enantiomerically pure 4-pyrrolidino derivatives, processes for their preparation, pharmaceutical compositions comprising said derivatives, and their use in the prevention and treatment of illness, in particular which is mediated by monoamine oxidase B inhibitors, in particular Alzheimer's disease or senile dementia.

  本发明涉及外消旋或对映纯的4-吡咯烷基衍生物，其制备方法，包含该衍生物的制药组合物，以及它们在预防和治疗疾病方面的应用，特别是通过单胺氧化酶B抑制剂介导的疾病，特别是阿尔茨海默病或老年性痴呆症。
• Multipathway bromination of stilbenes. Competition between carbonium and bromonium ion intermediates
  作者：Marie F. Ruasse、Jacques E. Dubois

  DOI：10.1021/jo00930a035

  日期：1974.8
• PYRROLIDONE DERIVATIVES AS MAOB INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1542969A1

  公开（公告）日：2005-06-22