3-甲氧基-6-硝基-2-(对甲苯磺酰基)苯甲醛 | 1026513-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基-6-硝基-2-(对甲苯磺酰基)苯甲醛
• 英文名称: 3-methoxy-6-nitro-2-(p-tolylsulfonyl)benzaldehyde
• 英文别名: (2-Formyl-6-methoxy-3-nitrophenyl) 4-methylbenzenesulfonate
• CAS: 1026513-31-4
• 化学式: C₁₅H₁₃NO₇S
• 分子量: 351.337
• InChiKey: OASQNHUVEJIYJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-甲氧基-6-硝基-2-(对甲苯磺酰基)苯甲醛 在 甲醇 作用下， 反应 0.5h， 生成 2-羟基-3-甲氧基-6-硝基苯甲醛
  参考文献：
  名称：

  Dihydroxynitrobenzaldehydes and hydroxymethoxynitrobenzaldehydes: synthesis and biological activity as catechol-O-methyltransferase inhibitors

  摘要：

  A series-of nitro derivatives of dihydroxy- and hydroxymethoxybenzaldehyde was synthesized and tested as potential inhibitors of partially purified pig liver catechol-O-methyltransferase (COMT). All the dihydroxynitrobenzaldehydes prepared were potent inhibitors of COMT, but only one hydroxymethoxynitrobenzaldehyde (3-hydroxy-4-methoxy-5-nitrobenzaldehyde) showed activity as a COMT inhibitor. Although previously reported data showed that the presence of electron-withdrawing substituents at position 5 seemed to be very important for activity as COMT inhibitor, our results suggest that the requirement necessary to enhance the activity of the dihydroxynitrobenzaldehyde derivatives toward COMT is the presence of the nitro group in a position ortho with respect to one hydroxyl group. The assayed compounds showed a reversible inhibition of COMT, which was mixed for all the dihydroxynitro derivatives but noncompetitive for 3-hydroxy-4-methoxy-5-nitrobenzaldehyde when pyrocatechol was the variable substrate and uncompetitive in all the inhibitors with respect to S-adenosyl-L-methionine.

  DOI：

  10.1021/jm00102a011
• 作为产物：
  描述：

  3-methoxy-2-<(p-tolylsulfonyl)oxy>benzaldehyde 生成 3-甲氧基-6-硝基-2-(对甲苯磺酰基)苯甲醛
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• A Photocleavable Auxiliary for Extended Native Chemical Ligation
  作者：Christina Nadler、André Nadler、Christine Hansen、Ulf Diederichsen

  DOI：10.1002/ejoc.201500033

  日期：2015.5

  To extend the scope of native chemical ligations beyond X-Cys connections, auxiliaries that contain thiol moieties were developed to mimic the function of the Cys residue in the ligation reaction/capture step. Auxiliaries known so far feature complicated attachment protocols and generally need harsh conditions for their cleavage. Herein, we present the development of a new photoremovable ligation auxiliary

  为了将天然化学连接的范围扩展到 X-Cys 连接之外，开发了含有硫醇部分的辅助剂来模拟连接反应/捕获步骤中 Cys 残基的功能。迄今为止已知的助剂具有复杂的附着协议，并且通常需要苛刻的条件来进行切割。在这里，我们提出了一种新的光可去除连接辅助剂的开发，它很容易合成并通过还原胺化反应连接到含有多种 N 端氨基酸的肽上。Gly-Gly 和 Ala-Gly 连接处的连接以高转化率进行，并且可以通过使用温和的光解方案从最终产物中裂解辅助物。这种方法学上的进步是肽连接化学向前迈出的重要一步。
• ——
  作者：BANDURCO V. T.、 LEVINE S. D.、 MULVEY D. M.、 TOBIA A. J.

  DOI：——

  日期：——
• Dihydroxynitrobenzaldehydes and hydroxymethoxynitrobenzaldehydes: synthesis and biological activity as catechol-O-methyltransferase inhibitors
  作者：Rosa A. Perez、Eldiberto Fernandez-Alvarez、Ofelia Nieto、F. Javier Piedrafita

  DOI：10.1021/jm00102a011

  日期：1992.11

  A series-of nitro derivatives of dihydroxy- and hydroxymethoxybenzaldehyde was synthesized and tested as potential inhibitors of partially purified pig liver catechol-O-methyltransferase (COMT). All the dihydroxynitrobenzaldehydes prepared were potent inhibitors of COMT, but only one hydroxymethoxynitrobenzaldehyde (3-hydroxy-4-methoxy-5-nitrobenzaldehyde) showed activity as a COMT inhibitor. Although previously reported data showed that the presence of electron-withdrawing substituents at position 5 seemed to be very important for activity as COMT inhibitor, our results suggest that the requirement necessary to enhance the activity of the dihydroxynitrobenzaldehyde derivatives toward COMT is the presence of the nitro group in a position ortho with respect to one hydroxyl group. The assayed compounds showed a reversible inhibition of COMT, which was mixed for all the dihydroxynitro derivatives but noncompetitive for 3-hydroxy-4-methoxy-5-nitrobenzaldehyde when pyrocatechol was the variable substrate and uncompetitive in all the inhibitors with respect to S-adenosyl-L-methionine.