β-nitroisoeugenol | 5395-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: β-nitroisoeugenol
• 英文别名: 4-Hydroxy-3-methoxyphenyl-2-nitropropene；2-methoxy-4-(2-nitroprop-1-enyl)phenol
• CAS: 5395-47-1
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD09697767
• 分子量: 209.202
• InChiKey: FDLWTEUMNRJFCS-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、甲苯

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-nitroisoeugenol 在 silica gel 、 L-Selectride 作用下， 生成 2-methoxy-4-(2-nitro-propyl)phenol
  参考文献：
  名称：

  Varma, Rajender S.; Kabalka, George W., Synthetic Communications, 1984, vol. 14, # 12, p. 1093 - 1098

  摘要：

  DOI：
• 作为产物：
  描述：

  硝基乙烷 、 香草醛 在 ammonium acetate 作用下， 反应 5.0h， 生成 β-nitroisoeugenol
  参考文献：
  名称：

  探索硝基苯乙烯作为新型 a 类单胺氧化酶抑制剂的支架

  摘要：

  With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a beta-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of beta-methyl-beta-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.

  DOI：

  10.2174/157018012804586888

文献信息

• Varma, Rajender S.; Kabalka, George W., Synthetic Communications, 1985, vol. 15, # 2, p. 151 - 156
  作者：Varma, Rajender S.、Kabalka, George W.

  DOI：——

  日期：——
• Varma, Rajender S.; Kabalka, George W., Synthetic Communications, 1984, vol. 14, # 12, p. 1093 - 1098
  作者：Varma, Rajender S.、Kabalka, George W.

  DOI：——

  日期：——
• Selected reductions of conjugated nitroalkenes
  作者：George W. Kabalka、Guindi M.H. Laila、Rajender S. Varma

  DOI：10.1016/s0040-4020(01)89059-1

  日期：1990.1
• Exploring Nitrostyrene as a Scaffold for a New Class a of Monoamine Oxidase Inhibitors
  作者：Joana Reis、Catarina Oliveira、Nuno Milhazes、Dolores Vina、Fernanda Borges

  DOI：10.2174/157018012804586888

  日期：2012.12.1

  With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a beta-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of beta-methyl-beta-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.