3,5-diiodo-2-methoxy-N-methyl-N-(4-phenoxyphenyl)benzamide | 1613336-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-diiodo-2-methoxy-N-methyl-N-(4-phenoxyphenyl)benzamide
• CAS: 1613336-62-1
• 化学式: C₂₁H₁₇I₂NO₃
• 分子量: 585.18
• InChiKey: NNDJLHXBJAFOGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-苯氧基-苯基)-乙酰胺 在 盐酸 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 乙二醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.33h， 生成 3,5-diiodo-2-methoxy-N-methyl-N-(4-phenoxyphenyl)benzamide
  参考文献：
  名称：

  Dual Protonophore–Chitinase Inhibitors Dramatically Affect O. volvulus Molting

  摘要：

  The L3-stage-specific chitinase OvCHT1 has been implicated in the development of Onchocerca volvulus, the causative agent of ondiocerciasis. Closantel, a known anthelmintic drug, was previously discovered as a potent and specific OvCHT1 inhibitor. As closantel is also a known protonophore, we performed a simple scaffold modulation to map out the structural features that are relevant for its individual or dual biochemical roles. Furthermore, we present that either OvCHT1 inhibition or protonophoric activity was capable of affecting O. volvulus L3 molting and that the presence of both activities in a single molecule yielded more potent inhibition of the nematode's developmental process.

  DOI：

  10.1021/jm5006435

文献信息

• Dual Protonophore–Chitinase Inhibitors Dramatically Affect <i>O. volvulus</i> Molting
  作者：Major Gooyit、Nancy Tricoche、Sara Lustigman、Kim D. Janda

  DOI：10.1021/jm5006435

  日期：2014.7.10

  The L3-stage-specific chitinase OvCHT1 has been implicated in the development of Onchocerca volvulus, the causative agent of ondiocerciasis. Closantel, a known anthelmintic drug, was previously discovered as a potent and specific OvCHT1 inhibitor. As closantel is also a known protonophore, we performed a simple scaffold modulation to map out the structural features that are relevant for its individual or dual biochemical roles. Furthermore, we present that either OvCHT1 inhibition or protonophoric activity was capable of affecting O. volvulus L3 molting and that the presence of both activities in a single molecule yielded more potent inhibition of the nematode's developmental process.