3-acetoxy-4-methoxy-2-nitrobenzaldehyde | 213040-67-6

• 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: 3-acetoxy-4-methoxy-2-nitrobenzaldehyde
• 英文别名: (3-Formyl-6-methoxy-2-nitrophenyl) acetate
• CAS: 213040-67-6
• 化学式: C₁₀H₉NO₆
• 分子量: 239.185
• InChiKey: MAOQBPIFIOOEIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetoxy-4-methoxy-2-nitrobenzaldehyde 在 silica gel 、 双(三甲基硅烷基)氨基钾 、 铁粉 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.17h， 生成 acetic acid 6-methoxy-1H-indol-7-yl ester
  参考文献：
  名称：

  Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum

  摘要：

  Three new indolequinones, 6-merhoxyindole-4,7-quinone (1), 5-methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established by spectroscopic methods and total synthesis, whereas the structure of 3 was elucidated mainly by NMR spectroscopic analyses. Compounds 1 3 exhibited moderate antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with MIC = 6.25 similar to 50 mu g/mL. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00593-6
• 作为产物：
  描述：

  3-羟基-4-甲氧基-2-硝基苯甲醛 、 乙酸酐 在 sodium acetate 作用下， 反应 2.5h， 以87%的产率得到3-acetoxy-4-methoxy-2-nitrobenzaldehyde
  参考文献：
  名称：

  Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum

  摘要：

  Three new indolequinones, 6-merhoxyindole-4,7-quinone (1), 5-methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established by spectroscopic methods and total synthesis, whereas the structure of 3 was elucidated mainly by NMR spectroscopic analyses. Compounds 1 3 exhibited moderate antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with MIC = 6.25 similar to 50 mu g/mL. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00593-6

文献信息

• Synthesis and Evaluation of 3-Aroylindoles as Anticancer Agents: Metabolite Approach
  作者：Yu-Shan Wu、Mohane Selvaraj Coumar、Jang-Yang Chang、Hsu-Yi Sun、Fu-Ming Kuo、Ching-Chuan Kuo、Ying-Jun Chen、Chi-Yen Chang、Chia-Ling Hsiao、Jing-Ping Liou、Ching-Ping Chen、Hsien-Tsung Yao、Yi-Kun Chiang、Uan-Kang Tan、Chiung-Tong Chen、Chang-Ying Chu、Su-Ying Wu、Teng-Kuang Yeh、Chin-Yu Lin、Hsing-Pang Hsieh

  DOI：10.1021/jm900060s

  日期：2009.8.13

  BPR0L075 (2) is a potential anticancer drug candidate designed from Combretastatin A-4 (1) based on the bioisosterism principle. Metabolites of 2, proposed from in vitro human microsome studies, were synthesized, leading to the identification of metabolitc-derived analogue 10 with 40-350 pM potency against various cancer cell lines. Insights gained from the major inactive metabolite of 2 led to the development of 29, with better pharmacokinetics and improved potency in the tumor xenograft model than 2.