N-(3-chloro-4-(4-chloro-2-hydroxyphenoxy)phenyl)naphthalene-2-sulfonamide | 871103-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-chloro-4-(4-chloro-2-hydroxyphenoxy)phenyl)naphthalene-2-sulfonamide
• 英文别名: N-[3-chloro-4-(4-chloro-2-hydroxyphenoxy)phenyl]naphthalene-2-sulfonamide
• CAS: 871103-71-8
• 化学式: C₂₂H₁₅Cl₂NO₄S
• 分子量: 460.337
• InChiKey: RNRMSZOJNYPGJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3-chloro-4-(4-chloro-2-methoxyphenoxy)phenyl)naphthalene-2-sulfonamide 在 三溴化硼 作用下， 生成 N-(3-chloro-4-(4-chloro-2-hydroxyphenoxy)phenyl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  Synthesis, biological activity, and X-ray crystal structural analysis of diaryl ether inhibitors of malarial enoyl acyl carrier protein reductase. Part 1: 4′-Substituted triclosan derivatives

  摘要：

  A structure-based approach has been taken to develop 4'-substituted analogs of triclosan that target the key malarial enzyme Plasmodium falciparum enoyl acyl carrier protein reductase (PfENR). Many of these compounds exhibit nanomolar potency against purified PfENR enzyme and modest (2-10microM) potency against in vitro cultures of drug-resistant and drug-sensitive strains of the P. falciparum parasite. X-ray crystal structures of nitro 29, aniline 30, methylamide 37, and urea 46 demonstrate the presence of hydrogen-bonding interactions with residues in the active site and point to future rounds of optimization to improve compound potency against purified enzyme and intracellular parasites.

  DOI：

  10.1016/j.bmcl.2005.08.044

文献信息

• Synthesis, biological activity, and X-ray crystal structural analysis of diaryl ether inhibitors of malarial enoyl acyl carrier protein reductase. Part 1: 4′-Substituted triclosan derivatives
  作者：Joel S. Freundlich、John W. Anderson、Dimitri Sarantakis、Hong-Ming Shieh、Min Yu、Juan-Carlos Valderramos、Edinson Lucumi、Mack Kuo、William R. Jacobs、David A. Fidock、Guy A. Schiehser、David P. Jacobus、James C. Sacchettini

  DOI：10.1016/j.bmcl.2005.08.044

  日期：2005.12

  A structure-based approach has been taken to develop 4'-substituted analogs of triclosan that target the key malarial enzyme Plasmodium falciparum enoyl acyl carrier protein reductase (PfENR). Many of these compounds exhibit nanomolar potency against purified PfENR enzyme and modest (2-10microM) potency against in vitro cultures of drug-resistant and drug-sensitive strains of the P. falciparum parasite. X-ray crystal structures of nitro 29, aniline 30, methylamide 37, and urea 46 demonstrate the presence of hydrogen-bonding interactions with residues in the active site and point to future rounds of optimization to improve compound potency against purified enzyme and intracellular parasites.