2-(4-methoxy-phenyl)-3,5-diphenyl-tetrazolium; chloride | 100628-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxy-phenyl)-3,5-diphenyl-tetrazolium; chloride
• 英文别名: 2-(4-Methoxyphenyl)-3,5-diphenyltetrazol-2-ium;chloride
• CAS: 100628-08-8
• 化学式: C₂₀H₁₇N₄O*Cl
• 分子量: 364.834
• InChiKey: OGEIQFSXEAULSR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-3,5-diphenylformazan 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以95%的产率得到2-(4-methoxy-phenyl)-3,5-diphenyl-tetrazolium; chloride
  参考文献：
  名称：

  铜路易斯酸表面活性剂催化制备氯化-3-取 代-2,5-二苯基四氮唑的方法

  摘要：

  本发明属于有机合成技术领域，具体涉及一种以铜路易斯酸表面活性剂为催化剂制备氯化‑3‑取代‑2,5‑二苯基四氮唑类化合物的方法，其包括以下步骤：1)以铜路易斯酸表面活性剂Cu(OSO2CnH2n+1)2为催化剂，苯甲醛、苯肼、芳香基胺和亚硝酸钠在溶剂水中反应得到3‑芳香基‑2,5‑二苯基甲臜；2)3‑芳香基‑2,5‑二苯基甲臜在二氯甲烷和水的混合溶剂中，在固体氯化试剂N‑氯代丁二酰亚胺的条件下进行关环和氯化，得到氯化‑3‑芳香基‑2,5‑二苯基四氮唑。该方法以“一锅法”连续的策略完成三步转化，不仅省略了中间的分离步骤，而且提纯步骤简单，简便易操作。

  公开号：

  CN108440433B

文献信息

• Anti-Plasmodium activity of tetrazolium salts
  作者：Xilin Cui、Jason Z. Vlahakis、Ian E. Crandall、Walter A. Szarek

  DOI：10.1016/j.bmc.2007.11.005

  日期：2008.2.15

  We have previously reported that sulfated cyclodextrins inhibit the invasion of Plasmodium merozoites by interacting with receptors present on the surface of erythrocytes. The observation that tetrazolium salts formed stable complexes with the inhibitory sulfated cyclodextrins suggested that tetrazolium salts might have anti-Plasmodium activity as well. Evaluation of commercially available tetrazolium salts indicated that some were active in the low nanomolar range and showed specificity in their inhibition of Plasmodium. Synthesis of a further 54 structures allowed us to determine that activity results from an aromatic component attached to the tetrazolium carbon atom (R-1) and its size is not critical to the activity of the compound. Nitro modi. cations of active compounds are poorly tolerated, however, the presence of halogen atoms on aromatic groups attached to the nitrogen atoms of the tetrazolium ring (R-2 and R-3) has little effect on activity. Methoxy groups are tolerated on R-2 and R-3 components; however, they are disruptive on the R-1 component. The overall results suggest that the R-1 component is interacting with a specific hydrophobic environment and the R-2 and R-3 components are less constrained. The activity of these compounds in several human and mouse Plasmodium cultures suggests that the compounds interact with a component of the parasite that is both essential and conserved. (c) 2007 Elsevier Ltd. All rights reserved.
• Wedekind, Chemische Berichte, 1896, vol. 29, p. 1849,1852
  作者：Wedekind

  DOI：——

  日期：——