N-(4-acetyl-2-bromophenyl)-2-(4-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)acetamide | 1188890-63-2

• 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-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)acetamide
• 英文别名: N-(4-acetyl-2-bromo-phenyl)-2-[4-(2,4-dibromophenyl)thiadiazol-5-yl]sulfanyl-acetamide；N-(4-acetyl-2-bromophenyl)-2-[4-(2,4-dibromophenyl)thiadiazol-5-yl]sulfanylacetamide
• CAS: 1188890-63-2
• 化学式: C₁₈H₁₂Br₃N₃O₂S₂
• 分子量: 606.156
• InChiKey: WHFASMNSBJKQKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-chloro-N-(4-ethanoyl-2-bromophenyl)ethanamide 、 sodium 4-(2,4-dibromophenyl)-1,2,3-thiadiazole-5-thiolate 以 乙醇 为溶剂， 以74.1%的产率得到N-(4-acetyl-2-bromophenyl)-2-(4-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)acetamide
  参考文献：
  名称：

  Novel 1,2,3-thiadiazole derivatives as HIV-1 NNRTIs with improved potency: Synthesis and preliminary SAR studies

  摘要：

  A novel synthetic route and anti-HIV activity evaluation of a new series of 2-(4-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)acetamide (TTA) derivatives are described. Bioactivity assay indicated that most of the title compounds showed good activities against HIV-1. In particular, compound 7c displayed the most potent anti-HIV-1 activity (EC50 = 36.4 nM), inhibiting HIV-1 replication in MT-4 cells more effectively than NVP (by sevenfold) and DLV (by eightfold). The preliminary structure-activity relationships (SAR) of the newly synthesized congeners are discussed, and molecular modeling of compound 7c in complex with HIV-1 RT is described, allowing rationalization of some SAR conclusions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.004

文献信息

• Novel 1,2,3-thiadiazole derivatives as HIV-1 NNRTIs with improved potency: Synthesis and preliminary SAR studies
  作者：Peng Zhan、Xinyong Liu、Zhenyu Li、Zengjun Fang、Zhong Li、Defeng Wang、Christophe Pannecouque、Erik De Clercq

  DOI：10.1016/j.bmc.2009.07.004

  日期：2009.8

  A novel synthetic route and anti-HIV activity evaluation of a new series of 2-(4-(2,4-dibromophenyl)-1,2,3-thiadiazol-5-ylthio)acetamide (TTA) derivatives are described. Bioactivity assay indicated that most of the title compounds showed good activities against HIV-1. In particular, compound 7c displayed the most potent anti-HIV-1 activity (EC50 = 36.4 nM), inhibiting HIV-1 replication in MT-4 cells more effectively than NVP (by sevenfold) and DLV (by eightfold). The preliminary structure-activity relationships (SAR) of the newly synthesized congeners are discussed, and molecular modeling of compound 7c in complex with HIV-1 RT is described, allowing rationalization of some SAR conclusions. (C) 2009 Elsevier Ltd. All rights reserved.