5-(3-氯苯基)-4-异丁基-4H-1,2,4-噻唑-3-硫醇 | 26028-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3-氯苯基)-4-异丁基-4H-1,2,4-噻唑-3-硫醇
• 英文名称: 5-(3-chloro-phenyl)-4-isobutyl-2,4-dihydro-[1,2,4]triazole-3-thione
• 英文别名: 3-(3-chlorophenyl)-4-(2-methylpropyl)-1H-1,2,4-triazole-5-thione
• CAS: 26028-64-8
• 化学式: C₁₂H₁₄ClN₃S
• mdl: MFCD05150471
• 分子量: 267.782
• InChiKey: NPNVFRBBSDZLNK-UHFFFAOYSA-N

物化性质

• 沸点：
  347.7±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  1-(3-chlorobenzoyl)-4-isobutylthiosemicarbazide 在 sodium hydroxide 作用下， 反应 2.0h， 以80%的产率得到5-(3-氯苯基)-4-异丁基-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies

  摘要：

  The treatment of epilepsy remains difficult mostly since almost 30% of patients suffer from pharmacoresistant forms of the disease. Therefore, there is an urgent need to search for new antiepileptic drug candidates. Previously, it has been shown that 4-alkyl-5-substituted-1,2,4-triazole-3-thione derivativatives possessed strong anticonvulsant activity in a maximal electroshock-induced seizure model of epilepsy. In this work, we examined the effect of the chemical structure of the 1,2,4-triazole-3-thione-based molecules on the anticonvulsant activity and the binding to voltage-gated sodium channels (VGSCs) and GABA(A) receptors. Docking simulations allowed us to determine the mode of interactions between the investigated compounds and binding cavity of the human VGSC. Selected compounds were also investigated in a panel of ADME-Tox assays, including parallel artificial membrane permeability assay (PAMPA), single cell gel electrophoresis (SCGE) and cytotoxicity evaluation in HepG2 cells. The obtained results indicated that unbranched alkyl chains, from butyl to hexyl, attached to 1,2,4-triazole core are essential both for good anticonvulsant activity and strong interactions with VGSCs. The combined in-vivo, in-vitro and in-silico studies emphasize 4-alkyl-5-substituted-1,2,4-triazole-3-thiones as promising agents in the development of new anticonvulsants.

  DOI：

  10.1016/j.ejps.2018.12.018

文献信息

• Surface Modified Metal Nano-Particle and Use Thereof
  申请人：LEE Sang Joon

  公开号：US20120168681A1

  公开（公告）日：2012-07-05

  The present invention provides a metal nanoparticle that is surface-modified with a hydrophilic or hydrophobic functional group, and a composition for optical detection comprising the same. The surface-modified nanoparticles according to the present invention form clusters suitable for optical detection, for example, suitable as an X-ray contrast agent, and have surface plasmon energy in the visible region, thereby being usefully applied to a variety of optical detection methods.
• US8753895B2
  申请人：——

  公开号：US8753895B2

  公开（公告）日：2014-06-17
• Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies
  作者：Barbara Kaproń、Jarogniew J. Łuszczki、Anita Płazińska、Agata Siwek、Tadeusz Karcz、Anna Gryboś、Gabriel Nowak、Anna Makuch-Kocka、Katarzyna Walczak、Ewa Langner、Karolina Szalast、Sebastian Marciniak、Magdalena Paczkowska、Judyta Cielecka-Piontek、Lukasz M. Ciesla、Tomasz Plech

  DOI：10.1016/j.ejps.2018.12.018

  日期：2019.3

  The treatment of epilepsy remains difficult mostly since almost 30% of patients suffer from pharmacoresistant forms of the disease. Therefore, there is an urgent need to search for new antiepileptic drug candidates. Previously, it has been shown that 4-alkyl-5-substituted-1,2,4-triazole-3-thione derivativatives possessed strong anticonvulsant activity in a maximal electroshock-induced seizure model of epilepsy. In this work, we examined the effect of the chemical structure of the 1,2,4-triazole-3-thione-based molecules on the anticonvulsant activity and the binding to voltage-gated sodium channels (VGSCs) and GABA(A) receptors. Docking simulations allowed us to determine the mode of interactions between the investigated compounds and binding cavity of the human VGSC. Selected compounds were also investigated in a panel of ADME-Tox assays, including parallel artificial membrane permeability assay (PAMPA), single cell gel electrophoresis (SCGE) and cytotoxicity evaluation in HepG2 cells. The obtained results indicated that unbranched alkyl chains, from butyl to hexyl, attached to 1,2,4-triazole core are essential both for good anticonvulsant activity and strong interactions with VGSCs. The combined in-vivo, in-vitro and in-silico studies emphasize 4-alkyl-5-substituted-1,2,4-triazole-3-thiones as promising agents in the development of new anticonvulsants.