2-甲基亚硒酰-N-苯基苯甲酰胺 | 126543-39-3

• 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: 2-甲基亚硒酰-N-苯基苯甲酰胺
• 中文别名: 氨甲酸,[[2-(羟甲基)环丙基]甲基]-,1,1-二甲基乙基酯,反-(9CI)
• 英文名称: 2-(methylseleninyl)benzanilide
• 英文别名: 2-methylseleninyl-N-phenylbenzamide
• CAS: 126543-39-3
• 化学式: C₁₄H₁₃NO₂Se
• 分子量: 306.223
• InChiKey: FYLHBMBOIMQLJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基亚硒酰-N-苯基苯甲酰胺 以 甲醇 、 乙腈 为溶剂， 生成 依布硒
  参考文献：
  名称：

  抗炎化合物依布硒啉的抗氧化活性：通过硒酸和硒酸中间体的可逆环化途径。

  摘要：

  描述了一种修正的机制，该机制解释了有机硒化合物依布硒啉的谷胱甘肽过氧化物酶（GPx）样催化活性。结果表明依布硒啉与H（2）O（2）的反应产生硒酸作为唯一的氧化产物。硒酸的X射线晶体结构表明，硒原子参与了与羰基氧原子的非共价相互作用。在过量硫醇的存在下，依布硒啉中的Se-N键很容易被硫醇裂解，生成相应的硒烯基硫化物。如此产生的亚硒基硫化物在H（2）O（2）存在下发生歧化反应，生成二硒化物，其与H（2）O（2）反应生成硒酸和硒酸的混合物。向包含硒酸和硒酸的混合物中添加硫醇会导致亚硒基硫化物的形成。当反应混合物中硫醇的浓度相对较低时，硒酸会快速环化生成依布硒啉。另一方面，硒酸与二硒化物反应生成依卜硒林作为最终产物。DFT计算表明，与亚磺酸到相应的亚磺酰基酰胺相比，硒酸对相应的亚硒基酰胺的环化更有利。这表明依卜硒仑在各种条件下的再生可保护硒部分免受不可逆的失活，这可能是依卜硒仑的生物学活性的原因。

  DOI：

  10.1002/chem.200801258
• 作为产物：
  描述：

  2-甲基硒基苯甲酰苯胺 在 peroxynitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-甲基亚硒酰-N-苯基苯甲酰胺
  参考文献：
  名称：

  The Reaction of 2-(Methylseleno)benzanilide with Peroxynitrite

  摘要：

  2-(Methylseleno)benzanilide (MeSe), a main metabolite of ebselen in vivo, rapidly reacts with peroxynitrite, yielding 2-(methylseleninyl)benzanilide (MeSe=O) as the sole selenium-containing product. The reaction proceeds efficiently at acidic pH where peroxynitrous acid (ONOOH) is predominant, suggesting that MeSe reacts faster with ONOOH than with the peroxynitrite anion (ONOO-). MeSe is much less reactive with hydrogen peroxide. The second-order rate constant for the reaction at 22 degrees C was estimated from the relationship between substrate consumption and peroxynitrite concentration as 2.2x10(4) M(-1) s(-1) and 2.7x10(3) M(-1) s(-1) at pH 3.9 and 7.0, respectively, and from intermolecular competition with ascorbic acid as 3.4x10(3) M(-1) s(-1) at pH 7.1. The rate constant is about 2 orders of magnitude lower than that for the reaction of ebselen with peroxynitrite, but about 1-2 orders of magnitude higher than that reported in the literature for methionine or ascorbate. The selenoxide can be reduced back to MeSe by thiols. MeSe has previously been considered to be an inert metabolite of ebselen, but may show antioxidant activity against peroxynitrite.

  DOI：

  10.1021/tx9600560

文献信息

• Antioxidant Activity of the Anti-Inflammatory Compound Ebselen: A Reversible Cyclization Pathway via Selenenic and Seleninic Acid Intermediates
  作者：Bani Kanta Sarma、Govindasamy Mugesh

  DOI：10.1002/chem.200801258

  日期：——

  A revised mechanism that accounts for the glutathione peroxidase (GPx)-like catalytic activity of the organoselenium compound ebselen is described. It is shown that the reaction of ebselen with H(2)O(2) yields seleninic acid as the only oxidized product. The X-ray crystal structure of the seleninic acid shows that the selenium atom is involved in a noncovalent interaction with the carbonyl oxygen atom

  描述了一种修正的机制，该机制解释了有机硒化合物依布硒啉的谷胱甘肽过氧化物酶（GPx）样催化活性。结果表明依布硒啉与H（2）O（2）的反应产生硒酸作为唯一的氧化产物。硒酸的X射线晶体结构表明，硒原子参与了与羰基氧原子的非共价相互作用。在过量硫醇的存在下，依布硒啉中的Se-N键很容易被硫醇裂解，生成相应的硒烯基硫化物。如此产生的亚硒基硫化物在H（2）O（2）存在下发生歧化反应，生成二硒化物，其与H（2）O（2）反应生成硒酸和硒酸的混合物。向包含硒酸和硒酸的混合物中添加硫醇会导致亚硒基硫化物的形成。当反应混合物中硫醇的浓度相对较低时，硒酸会快速环化生成依布硒啉。另一方面，硒酸与二硒化物反应生成依卜硒林作为最终产物。DFT计算表明，与亚磺酸到相应的亚磺酰基酰胺相比，硒酸对相应的亚硒基酰胺的环化更有利。这表明依卜硒仑在各种条件下的再生可保护硒部分免受不可逆的失活，这可能是依卜硒仑的生物学活性的原因。
• The Reaction of 2-(Methylseleno)benzanilide with Peroxynitrite
  作者：Hiroshi Masumoto、Helmut Sies

  DOI：10.1021/tx9600560

  日期：1996.1.1

  2-(Methylseleno)benzanilide (MeSe), a main metabolite of ebselen in vivo, rapidly reacts with peroxynitrite, yielding 2-(methylseleninyl)benzanilide (MeSe=O) as the sole selenium-containing product. The reaction proceeds efficiently at acidic pH where peroxynitrous acid (ONOOH) is predominant, suggesting that MeSe reacts faster with ONOOH than with the peroxynitrite anion (ONOO-). MeSe is much less reactive with hydrogen peroxide. The second-order rate constant for the reaction at 22 degrees C was estimated from the relationship between substrate consumption and peroxynitrite concentration as 2.2x10(4) M(-1) s(-1) and 2.7x10(3) M(-1) s(-1) at pH 3.9 and 7.0, respectively, and from intermolecular competition with ascorbic acid as 3.4x10(3) M(-1) s(-1) at pH 7.1. The rate constant is about 2 orders of magnitude lower than that for the reaction of ebselen with peroxynitrite, but about 1-2 orders of magnitude higher than that reported in the literature for methionine or ascorbate. The selenoxide can be reduced back to MeSe by thiols. MeSe has previously been considered to be an inert metabolite of ebselen, but may show antioxidant activity against peroxynitrite.