N-(4-acetyl-2-bromophenyl)-2-(4-(3,4-dichlorophenyl)-1,2,3-selenadiazol-5-ylthio)acetamide | 1190213-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetyl-2-bromophenyl)-2-(4-(3,4-dichlorophenyl)-1,2,3-selenadiazol-5-ylthio)acetamide
• 英文别名: N-(4-acetyl-2-bromo-phenyl)-2-[4-(3,4-dichlorophenyl)selenadiazol-5-yl]sulfanyl-acetamide；N-(4-acetyl-2-bromophenyl)-2-[4-(3,4-dichlorophenyl)selenadiazol-5-yl]sulfanylacetamide
• CAS: 1190213-48-9
• 化学式: C₁₈H₁₂BrCl₂N₃O₂SSe
• 分子量: 564.148
• InChiKey: AQAONAHHUOHCNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-chloro-N-(4-ethanoyl-2-bromophenyl)ethanamide 、 sodium 4-(3,4-dichlorophenyl)-1,2,3-selenadiazole-5-thiolate 以 乙醇 为溶剂， 以85.7%的产率得到N-(4-acetyl-2-bromophenyl)-2-(4-(3,4-dichlorophenyl)-1,2,3-selenadiazol-5-ylthio)acetamide
  参考文献：
  名称：

  1,2,3-Selenadiazole thioacetanilides: Synthesis and anti-HIV activity evaluation

  摘要：

  The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel structures of increased potency. Based on the bioisosteric principle, novel series of 1,2,3-selenadiazole thioacetanilide derivatives were designed, and synthesized using an original synthetic route, structurally confirmed by spectral analysis, and evaluated for their anti-HIV activity in MT-4 cells. The results showed that only compound 7f possessed potent activity against HIV-1 replication (EC50 = 2.45 mu M) similar to the prototype series of sulfanyltriazoles. None of the compounds were active against HIV-2 replication. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.027

文献信息

• 1,2,3-Selenadiazole thioacetanilides: Synthesis and anti-HIV activity evaluation
  作者：Peng Zhan、Xinyong Liu、Zengjun Fang、Christophe Pannecouque、Erik De Clercq

  DOI：10.1016/j.bmc.2009.07.027

  日期：2009.9.1

  The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel structures of increased potency. Based on the bioisosteric principle, novel series of 1,2,3-selenadiazole thioacetanilide derivatives were designed, and synthesized using an original synthetic route, structurally confirmed by spectral analysis, and evaluated for their anti-HIV activity in MT-4 cells. The results showed that only compound 7f possessed potent activity against HIV-1 replication (EC50 = 2.45 mu M) similar to the prototype series of sulfanyltriazoles. None of the compounds were active against HIV-2 replication. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.