[2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chlorophenyl] N-methyl-N-[2-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]-2-oxoethyl]carbamate | 1417795-55-1

• 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: [2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chlorophenyl] N-methyl-N-[2-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]-2-oxoethyl]carbamate
• CAS: 1417795-55-1
• 化学式: C₂₄H₂₃ClF₆N₄O₆
• 分子量: 612.913
• InChiKey: WZJKXRFVIVCOBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chlorophenyl] N-methyl-N-[2-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]-2-oxoethyl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以94%的产率得到[2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chlorophenyl] N-(2-hydrazinyl-2-oxoethyl)-N-methylcarbamate;hydrochloride
  参考文献：
  名称：

  Salicylanilide Inhibitors of Toxoplasma gondii

  摘要：

  Toxoplasma gondii (T. gondii) is an apicomplexan parasite that can cause eye disease, brain disease, and death, especially in congenitally infected and immune-compromised people. Novel medicines effective against both active and latent forms of the parasite are greatly needed. The current study focused on the discovery of such medicines by exploring a family of potential inhibitors whose antiapicomplexan activity has not been previously reported. Initial screening efforts revealed that niclosamide, a drug approved for anthelmintic use, possessed promising activity in vitro against T. gondii. This observation inspired the evaluation of the activity of a series of salicylanilides and derivatives. Several inhibitors with activities in the nanomolar range with no appreciable in vitro toxicity to human cells were identified. An initial structure activity relationship was explored. Four compounds were selected for evaluation in an in vivo model of infection, and two derivatives with potentially enhanced pharmacological parameters demonstrated the best activity profiles.

  DOI：

  10.1021/jm3007596
• 作为产物：
  描述：

  N-[3,5-双(三氟甲基)苯基]-5-氯-2-羟基苯甲酰胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-4-chlorophenyl] N-methyl-N-[2-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]-2-oxoethyl]carbamate
  参考文献：
  名称：

  Salicylanilide Inhibitors of Toxoplasma gondii

  摘要：

  Toxoplasma gondii (T. gondii) is an apicomplexan parasite that can cause eye disease, brain disease, and death, especially in congenitally infected and immune-compromised people. Novel medicines effective against both active and latent forms of the parasite are greatly needed. The current study focused on the discovery of such medicines by exploring a family of potential inhibitors whose antiapicomplexan activity has not been previously reported. Initial screening efforts revealed that niclosamide, a drug approved for anthelmintic use, possessed promising activity in vitro against T. gondii. This observation inspired the evaluation of the activity of a series of salicylanilides and derivatives. Several inhibitors with activities in the nanomolar range with no appreciable in vitro toxicity to human cells were identified. An initial structure activity relationship was explored. Four compounds were selected for evaluation in an in vivo model of infection, and two derivatives with potentially enhanced pharmacological parameters demonstrated the best activity profiles.

  DOI：

  10.1021/jm3007596