2-hydroxy-3,5-diiodo-N-(naphthalen-2-yl)benzamide | 1613336-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3,5-diiodo-N-(naphthalen-2-yl)benzamide
• 英文别名: 2-hydroxy-3,5-diiodo-N-naphthalen-2-ylbenzamide
• CAS: 1613336-70-1
• 化学式: C₁₇H₁₁I₂NO₂
• 分子量: 515.089
• InChiKey: MJQBWIKDVPOWEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二碘水杨酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-hydroxy-3,5-diiodo-N-(naphthalen-2-yl)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

• METHODS FOR TREATMENT OF CLOSTRIDIUM DIFFICILE INFECTIONS
  申请人：The Scripps Research Institute

  公开号：US20190350891A1

  公开（公告）日：2019-11-21

  In this study, we capitalized on the antimicrobial property and low oral bioavailability of known salicylanilide anthelmintics (closantel, rafoxanide, niclosamide, oxyclozanide) to target the gut pathogen. The anthelmintics displayed excellent potency against C. difficile strains 630 and 4118 (with MIC values as low as 0.06-0.13 μg/mL for rafoxanide) via a membrane depolarization mechanism, interestingly, closantel, rafoxanide and compound 8 were bactericidal against logarithmic- and stationary-phase cultures of the BI/NAP1/027 strain 4118. Further evaluation of the salicylanilides showed their preferential activity against Gram-positive over Gram-negative bacteria. Moreover, the salicylanilides were non-hemolytic and were non-toxic to mammalian cell lines HepG2 and HEK 293T/17 within the range of their in vitro MICs and MBCs. The salicylanilide anthelmintics exhibit desirable bactericidal and pharmacokinetic properties and are amenable to repositioning as anti- C. difficile agents.
• 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.