1-(2-羟基-3-甲氧基-5-硝基苯基)乙酮 | 6342-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-羟基-3-甲氧基-5-硝基苯基)乙酮
• 英文名称: 1-(2-hydroxy-3-methoxy-5-nitro-phenyl)-ethanone
• 英文别名: 1-(2-Hydroxy-3-methoxy-5-nitro-phenyl)-aethanon；1-(2-Hydroxy-3-methoxy-5-nitrophenyl)ethanone
• CAS: 6342-65-0
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: YXAQTQBNKODJMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-3-甲氧基-5-硝基苯基)乙酮 在 三乙烯二胺 、 tin(II) chloride dihdyrate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 41.0h， 生成 (3-methyl-7-methoxy-5-aminobenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Concise Synthesis and Biological Evaluation of 2-Aroyl-5-Amino Benzo[b]thiophene Derivatives As a Novel Class of Potent Antimitotic Agents

  摘要：

  The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of tubulin. The position of the methoxy group on the benzo[b]thiophene was important for maximal antiproliferative activity. Structure-activity relationship analysis established that the best activities were obtained with amino and methoxy groups placed at the C-5 and C-7 positions, respectively. Compounds 3c-e showed more potent inhibition of tubulin polymerization than combretastatin A-4 and strong binding to the colchicine site. These compounds also demonstrated substantial antiproliferative activity, with IC50 values ranging from 2.6 to 18 nM in a variety of cancer cell lines. Importantly, compound 3c (50 mg/kg), significantly inhibited the growth of the human osteosarcoma MNNG/HOS xenograft in nude mice.

  DOI：

  10.1021/jm4013938
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 硝酸 、 溶剂黄146 作用下， 生成 1-(2-羟基-3-甲氧基-5-硝基苯基)乙酮
  参考文献：
  名称：

  Hydrogen Bromide Cleavage of Hindered 2-Methoxyacetophenones

  摘要：

  DOI：

  10.1021/ja01543a027

文献信息

• Synthesis and Antitumor Molecular Mechanism of Agents Based on Amino 2-(3′,4′,5′-Trimethoxybenzoyl)benzo[b]furan: Inhibition of Tubulin and Induction of Apoptosis
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Carlota Lopez-Cara、Olga Cruz-Lopez、Maria Dora Carrion、Maria Kimatrai Salvador、Jaime Bermejo、Sara Estévez、Francisco Estévez、Jan Balzarini、Andrea Brancale、Antonio Ricci、Longchuan Chen、Jae Gwan Kim、Ernest Hamel

  DOI：10.1002/cmdc.201100279

  日期：2011.10.4

  compound in this series is 2‐(3′,4′,5′‐trimethoxybenzoyl)‐3‐methyl‐5‐amino‐6‐methoxybenzo[b]furan (3 h), which inhibits cancer cell growth at nanomolar concentrations (IC50=16–24 nM), and interacts strongly with tubulin by binding to the colchicine site. Sub‐G1 apoptotic cells in cultures of HL‐60 and U937 cells were observed by flow cytometric analysis after treatment with 3 h in a concentration‐dependent

  诱导细胞凋亡是一种很有前景的策略，可以导致发现在癌症化疗中具有活性的新分子。当细胞用靶向微管的试剂处理时，通常会观察到这种特性，微管是在细胞分裂中起关键作用的动态结构。苯并[ b ]呋喃等小分子作为微管蛋白聚合的抑制剂很有吸引力。合成并评价了一类基于2-(3',4',5'-三甲氧基苯甲酰基)苯并[ b ]呋喃分子骨架，氨基位于苯环不同位置的新型微管蛋白聚合抑制剂用于抗增殖活性、抑制微管蛋白聚合和细胞周期效应。苯并[ b的苯部分上的甲氧基取代模式]呋喃部分在影响抗增殖活性中起重要作用。在 5-氨基衍生物系列中，如果甲氧基取代基位于 C6 位置，则对细胞生长的抑制作用最大，而 C7 取代基会降低效力。该系列中最有前景的化合物是 2-(3',4',5'-三甲氧基苯甲酰基)-3-甲基-5-氨基-6-甲氧基苯并[ b ]呋喃 ( 3 h )，它以纳摩尔水平抑制癌细胞生长浓度 (IC 50 =16–24
• Azo compounds and material colored therewith
  申请人：EASTMAN KODAK CO

  公开号：US02317365A1

  公开（公告）日：1943-04-27
• Concise Synthesis and Biological Evaluation of 2-Aroyl-5-Amino Benzo[<i>b</i>]thiophene Derivatives As a Novel Class of Potent Antimitotic Agents
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Carlota Lopez-Cara、Delia Preti、Mojgan Aghazadeh Tabrizi、Jan Balzarini、Marcella Bassetto、Andrea Brancale、Xian-Hua Fu、Yang Gao、Jun Li、Su-Zhan Zhang、Ernest Hamel、Roberta Bortolozzi、Giuseppe Basso、Giampietro Viola

  DOI：10.1021/jm4013938

  日期：2013.11.27

  The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of tubulin. The position of the methoxy group on the benzo[b]thiophene was important for maximal antiproliferative activity. Structure-activity relationship analysis established that the best activities were obtained with amino and methoxy groups placed at the C-5 and C-7 positions, respectively. Compounds 3c-e showed more potent inhibition of tubulin polymerization than combretastatin A-4 and strong binding to the colchicine site. These compounds also demonstrated substantial antiproliferative activity, with IC50 values ranging from 2.6 to 18 nM in a variety of cancer cell lines. Importantly, compound 3c (50 mg/kg), significantly inhibited the growth of the human osteosarcoma MNNG/HOS xenograft in nude mice.
• Hydrogen Bromide Cleavage of Hindered 2-Methoxyacetophenones
  作者：W. J. Horton、Jack T. Spence

  DOI：10.1021/ja01543a027

  日期：1958.5