3-benzyl-1-methyl-(1H)-imidazole-2(3H)-selone | 920519-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-benzyl-1-methyl-(1H)-imidazole-2(3H)-selone
• 英文别名: 1-Benzyl-3-methylimidazole-2-selone；1-benzyl-3-methylimidazole-2-selone
• CAS: 920519-25-1
• 化学式: C₁₁H₁₂N₂Se
• 分子量: 251.19
• InChiKey: ZLCVZLRKUXQSBS-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  334.6±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-methyl-(1H)-imidazole-2(3H)-selone 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到1-benzyl-2-(diiodo-l4-selaneylidene)-3-methyl-2,3-dihydro-1H-imidazole
  参考文献：
  名称：

  Interactions of Antithyroid Drugs and Their Analogues with Halogens and their Biological Implications

  摘要：

  The selenium analogue of antithyroid drug methimazole (MSeI) reacts with molecular bromine to produce two different types of novel complexes depending upon the molar ratio of MSeI to Br-2 in the reaction medium: Dicationic diselenide complex with two Br- ions as counterions is produced in the reaction of MSeI with 0.5 equiv of Br-2 (MSeI/Br-2, 1.0:0.5), whereas a stable 10-Se-3 hypervalent "T-shaped" complex featuring a linear Br-Se-Br moiety was produced when MSeI was treated with Br-2 in an equimolar ratio (MSeI/Br-2, 1.0:1.0). A substitution at the free N-H group in MSeI alters its reactivity toward iodine/bromine. For example, the N,N-disubstituted selones exclusively produce the corresponding 10-Se-3 hypervalent "T-shaped" complexes in the reaction with I-2. In the presence of the lectoperoxidase/H2O2/I- system, N,N-dimethylimidazole-2-selone produces the corresponding dicationic diselenide with two I- counterions as the final metabolite. The formation of ionic species in these reactions is confirmed by single crystal X-ray diffraction studies and in some cases by Fourier transform-Raman spectroscopic investigations.

  DOI：

  10.1021/cg101688v
• 作为产物：
  描述：

  1-苄基-3-甲基咪唑氯盐 在 selenium 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-benzyl-1-methyl-(1H)-imidazole-2(3H)-selone
  参考文献：
  名称：

  咪唑基亚硫基和硒酮抑制乳过氧化物酶催化的氧化：机理研究。

  摘要：

  在本文中，我们描述了一系列包含咪唑药效基团的N，N-二取代的硫酮和色氨酸的合成和仿生活性。N，N-二取代的硫酮对LPO催化的氧化反应没有任何抑制活性，但它们相应的N，N-二取代的紫杉醇对LPO的氧化反应具有抑制作用。咪唑环N原子上的取代基似乎对LPO催化的氧化和碘化反应的抑制具有显著作用。Selones 16，17，和19，其中包含甲基，乙基，和苄基的取代基，表现出对与IC LPO催化氧化反应类似的抑制活性50个24.4，22.5，和22.5μ值中号，分别。但是，它们的活性几乎比常用的抗甲状腺药甲巯咪唑（MMI）低三倍。与此相反，selone 21，其中包含A N  CH 2 CH 2 OH取代基，显示出高抑制活性，具有的IC 50值的7.2μ中号，这是类似于MMI的。这些selones对LPO催化的氧化/碘化反应的抑制活性是由于它们能够通过催化还原H 2 O 2来降低共底物（H 2 O

  DOI：

  10.1002/asia.201300274

文献信息

• Chemical Detoxification of Organomercurials
  作者：Mainak Banerjee、Ramesh Karri、Kuber Singh Rawat、Karthick Muthuvel、Biswarup Pathak、Gouriprasanna Roy

  DOI：10.1002/anie.201504413

  日期：2015.8.3

  Organomercurials including methylmercury are ubiquitous environmental pollutants and highly toxic to humans. Now it could be shown that N‐methylimidazole based thiones/selones having an N‐CH2CH2OH substituent are remarkably effective in detoxifying various organomercurials to produce less toxic HgE (E=S, Se) nanoparticles. Compounds lacking the N‐CH2CH2OH substituent failed to produce HgE nanoparticles

  包括甲基汞在内的有机汞是普遍存在的环境污染物，对人类有剧毒。现在可以证明，具有N- CH 2 CH 2 OH取代基的基于N-甲基咪唑的硫酮/硒酮对多种有机汞的解毒作用非常有效，以产生毒性较小的HgE（E = S，Se）纳米颗粒。缺少N‐ CH 2 CH 2的化合物OH取代基在用有机汞处理后无法产生HgE纳米颗粒，表明该部分通过促进脱硫和脱硒过程在脱毒中起关键作用。这种新型的有机汞解毒方法可能会导致发现治疗甲基汞中毒患者的新化合物。
• Selenium Analogues of Anti-Thyroid Drugs
  作者：Gouriprasanna Roy、Govindasamy Mugesh

  DOI：10.1080/10426500801898259

  日期：2008.4.1

  In contrast to thiones and selones, the S- and Se-protected compounds do not show any noticeable inhibition under identical experimental conditions. While the inhibition of LPO by MMI cannot be reversed by increasing the hydrogen peroxide concentration, the inhibition by MSeI can be completely reversed by increasing the peroxide concentration. Experimental and theoretical studies were performed on

  描述了抗甲状腺药物和相关衍生物对乳过氧化物酶 (LPO) 催化氧化 ABTS 的抑制作用。常用的抗甲状腺药物甲巯咪唑 (MMI) 抑制 LPO 的 IC 50 值为 7.0 ± 1.1 μ M，远低于其他两种抗甲状腺药物 PTU 和 MTU。甲巯咪唑硒类似物 (MSeI) 也抑制 LPO，IC 50 值为 16.4 ± 1.5 μ M，比 PTU 和 MTU 低约 4-5 倍。与硫酮和硫酮相比，S-和Se-保护的化合物在相同的实验条件下没有表现出任何明显的抑制作用。虽然 MMI 对 LPO 的抑制不能通过增加过氧化氢浓度来逆转，但 MSeI 对 LPO 的抑制可以通过增加过氧化物浓度来完全逆转。对许多硒进行了实验和理论研究，这表明这些化合物以硒醇盐或两性离子的形式存在，其中硒原子带有大量负电荷。selones 的结构通过 NMR 光谱在溶液中进行研究，selones 的 77 Se NMR
• Antithyroid Drug Carbimazole and Its Analogues: Synthesis and Inhibition of Peroxidase-Catalyzed Iodination of <scp>l</scp>-Tyrosine
  作者：Debasis Das、Gouriprasanna Roy、Govindasamy Mugesh

  DOI：10.1021/jm800894m

  日期：2008.11.27

  Synthesis and biological activity of the antithyroid drug carbimazole (CBZ) and its analogues are described. The introduction of an ethoxycarbonyl group in methimazole and its selenium analogue not only prevents the oxidation to the corresponding disulfide and diselenide but also reduces the zwitterionic character. A structure-activity correlation in a series of CBZ analogues suggests that the presence of a methyl substituent in CBZ and related compounds is important for their antithyroid activity.
• Inhibition of Lactoperoxidase-Catalyzed Oxidation by Imidazole-Based Thiones and Selones: A Mechanistic Study
  作者：Gouriprasanna Roy、P. N. Jayaram、Govindasamy Mugesh

  DOI：10.1002/asia.201300274

  日期：2013.8

  N‐disubstituted thiones and selones that contain an imidazole pharmacophore. The N,N‐disubstituted thiones do not show any inhibitory activity towards LPO‐catalyzed oxidation reactions, but their corresponding N,N‐disubstituted selones exhibit inhibitory activity towards LPO‐catalyzed oxidation reactions. Substituents on the N atom of the imidazole ring appear to have a significant effect on the inhibition of LPO‐catalyzed

  在本文中，我们描述了一系列包含咪唑药效基团的N，N-二取代的硫酮和色氨酸的合成和仿生活性。N，N-二取代的硫酮对LPO催化的氧化反应没有任何抑制活性，但它们相应的N，N-二取代的紫杉醇对LPO的氧化反应具有抑制作用。咪唑环N原子上的取代基似乎对LPO催化的氧化和碘化反应的抑制具有显著作用。Selones 16，17，和19，其中包含甲基，乙基，和苄基的取代基，表现出对与IC LPO催化氧化反应类似的抑制活性50个24.4，22.5，和22.5μ值中号，分别。但是，它们的活性几乎比常用的抗甲状腺药甲巯咪唑（MMI）低三倍。与此相反，selone 21，其中包含A N  CH 2 CH 2 OH取代基，显示出高抑制活性，具有的IC 50值的7.2μ中号，这是类似于MMI的。这些selones对LPO催化的氧化/碘化反应的抑制活性是由于它们能够通过催化还原H 2 O 2来降低共底物（H 2 O
• Interactions of Antithyroid Drugs and Their Analogues with Halogens and their Biological Implications
  作者：Gouriprasanna Roy、Krishna P. Bhabak、Govindasamy Mugesh

  DOI：10.1021/cg101688v

  日期：2011.6.1

  The selenium analogue of antithyroid drug methimazole (MSeI) reacts with molecular bromine to produce two different types of novel complexes depending upon the molar ratio of MSeI to Br-2 in the reaction medium: Dicationic diselenide complex with two Br- ions as counterions is produced in the reaction of MSeI with 0.5 equiv of Br-2 (MSeI/Br-2, 1.0:0.5), whereas a stable 10-Se-3 hypervalent "T-shaped" complex featuring a linear Br-Se-Br moiety was produced when MSeI was treated with Br-2 in an equimolar ratio (MSeI/Br-2, 1.0:1.0). A substitution at the free N-H group in MSeI alters its reactivity toward iodine/bromine. For example, the N,N-disubstituted selones exclusively produce the corresponding 10-Se-3 hypervalent "T-shaped" complexes in the reaction with I-2. In the presence of the lectoperoxidase/H2O2/I- system, N,N-dimethylimidazole-2-selone produces the corresponding dicationic diselenide with two I- counterions as the final metabolite. The formation of ionic species in these reactions is confirmed by single crystal X-ray diffraction studies and in some cases by Fourier transform-Raman spectroscopic investigations.