2,3-dihydroxy-6-nitrobenzaldehyde | 144156-89-8

• 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: 2,3-dihydroxy-6-nitrobenzaldehyde
• 英文别名: Benzaldehyde, 2,3-dihydroxy-6-nitro-
• CAS: 144156-89-8
• 化学式: C₇H₅NO₅
• 分子量: 183.12
• InChiKey: NCTNMQLZSVOAKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基-6-硝基-2-(对甲苯磺酰基)苯甲醛 在 甲醇 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 65.5h， 生成 2,3-dihydroxy-6-nitrobenzaldehyde
  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

文献信息

• Iron-catalyzed arene C−H hydroxylation
  作者：Lu Cheng、Huihui Wang、Hengrui Cai、Jie Zhang、Xu Gong、Wei Han

  DOI：10.1126/science.abj0731

  日期：2021.10

  selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired l-cystine–derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation

  由于芳基碳氢键的相对惰性、酚类产物的较高反应性导致过度氧化的副产物以及经常不足的区域选择性，芳烃的可持续、非定向和选择性催化羟基化仍然是一项持续的研究挑战。我们报告说，铁由受生物启发的l-胱氨酸衍生的配体可以催化非定向芳烃碳氢羟基化，过氧化氢作为末端氧化剂。该反应以其广泛的底物范围、出色的选择性和良好的产率而著称，并且表现出与氧化敏感官能团的相容性，如醇、多酚、醛，甚至硼酸。该方法非常适合通过多重碳氢羟基化合成多酚，以及天然产物和药物分子的后期功能化。
• Synthesis and Biological Activity of 4-Amino-5-chloro-2-ethoxy-3-hydroxybenzamides, Metabolites of a New Gastroprokinetic Agent, Mosapride.
  作者：Shiro KATO、Toshiya MORIE、Naoyuki YOSHIDA

  DOI：10.1248/cpb.44.1484

  日期：——

  To confirm the proposed structures of the minor metabolites of a potential gastroprokinetic agent, mosapride, 4-amino-5-chloro-2-ethoxy-3-hydroxy-N-(2-morpholinylmethyl)benzamide (3) and the N-(5-oxo-2-morpholinyl)-methyl analogue 4 were prepared. As the common intermediate, 2-ethoxy-3-hydroxy-4-nitrobenzoic acid (15) was propared via the regioselective ethylation of 2, 3-dihydroxybenzaldehyde (10) and subsequent nitration of the resultant 2-ethoxy-3-hydroxybenzaldehyde (11). The key intermediate 15 was converted into the benzamides 3 and 4. After enzymatic treatment of the isolated metabolites, their structures were identified by comparison with the synthetic compounds. Serotonin-4 receptor binding affinity of these metabolites was found to be lower than that of mosapride.

  为了确认潜在胃动力药物莫沙普利的小分子代谢产物的提议结构，合成了4-amino-5-chloro-2-ethoxy-3-hydroxy-N-(2-morpholinylmethyl)benzamide (3)和N-(5-oxo-2-morpholinyl)-methyl类似物4。作为共同中间体，通过对2,3-二羟基苯甲醛 (10) 进行区域选择性的乙基化以及对生成的2-乙氧基-3-羟基苯甲醛 (11) 进行后续硝化，合成了2-乙氧基-3-羟基-4-硝基苯甲酸 (15)。关键中间体15转化为苯酰胺3和4。在对分离代谢产物进行酶促处理后，通过与合成化合物的比较确认了它们的结构。这些代谢产物的5-羟色胺4受体结合亲和力低于莫沙普利。
• AUXILIARY FOR AMIDE BOND FORMATION
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：EP1115739A1

  公开（公告）日：2001-07-18
• EP1115739A4
  申请人：——

  公开号：EP1115739A4

  公开（公告）日：2004-10-27
• US7718598B1
  申请人：——

  公开号：US7718598B1

  公开（公告）日：2010-05-18