3-[(2-Methoxyphenyl)-(2-naphthylsulfanyl)methyl]pyridine | 1384458-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[(2-Methoxyphenyl)-(2-naphthylsulfanyl)methyl]pyridine
• 英文别名: 3-[(2-methoxyphenyl)-naphthalen-2-ylsulfanylmethyl]pyridine
• CAS: 1384458-27-8
• 化学式: C₂₃H₁₉NOS
• 分子量: 357.476
• InChiKey: IRUWMALTAAHFNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 2-Methoxyphenylmagnesium bromide 以 四氢呋喃 、 苯 为溶剂， 反应 1.5h， 生成 3-[(2-Methoxyphenyl)-(2-naphthylsulfanyl)methyl]pyridine
  参考文献：
  名称：

  Aryl aryl methyl thio arenes prevent multidrug-resistant malaria in mouse by promoting oxidative stress in parasites

  摘要：

  We have synthesized a new series of aryl aryl methyl thio arenes (AAMTAs) and evaluated antimalarial activity in vitro and in vivo against drug-resistant malaria. These compounds interact with free heme, inhibit hemozoin formation, and prevent Plasmodium falciparum growth in vitro in a concentration-dependent manner. These compounds concentration dependently promote oxidative stress in Plasmodium falciparum as evident from the generation of intraparasitic oxidants, protein carbonyls, and lipid peroxidation products. Furthermore, AAMTAs deplete intraparasite GSH levels, which is essential for antioxidant defense and survival during intraerythrocytic stages. These compounds displayed potent antimalarial activity not only in vitro but also ill vivo against multidrug-resistant Plasmodium yoelii dose dependently in a mouse model. The mixtures of enantiomers of AAMTAs containing 3-pyridyl rings were found to be more efficient in providing antimalarial activity. Efforts have been made to synthesize achiral AAMTAs 17-23 and among them, compound 18 showed significant antimalarial activity in vivo (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2012.04.028

文献信息

• Aryl aryl methyl thio arenes prevent multidrug-resistant malaria in mouse by promoting oxidative stress in parasites
  作者：Manish Goyal、Priyanka Singh、Athar Alam、Sajal Kumar Das、Mohd Shameel Iqbal、Sumanta Dey、Samik Bindu、Chinmay Pal、Sanjit Kumar Das、Gautam Panda、Uday Bandyopadhyay

  DOI：10.1016/j.freeradbiomed.2012.04.028

  日期：2012.7

  We have synthesized a new series of aryl aryl methyl thio arenes (AAMTAs) and evaluated antimalarial activity in vitro and in vivo against drug-resistant malaria. These compounds interact with free heme, inhibit hemozoin formation, and prevent Plasmodium falciparum growth in vitro in a concentration-dependent manner. These compounds concentration dependently promote oxidative stress in Plasmodium falciparum as evident from the generation of intraparasitic oxidants, protein carbonyls, and lipid peroxidation products. Furthermore, AAMTAs deplete intraparasite GSH levels, which is essential for antioxidant defense and survival during intraerythrocytic stages. These compounds displayed potent antimalarial activity not only in vitro but also ill vivo against multidrug-resistant Plasmodium yoelii dose dependently in a mouse model. The mixtures of enantiomers of AAMTAs containing 3-pyridyl rings were found to be more efficient in providing antimalarial activity. Efforts have been made to synthesize achiral AAMTAs 17-23 and among them, compound 18 showed significant antimalarial activity in vivo (c) 2012 Elsevier Inc. All rights reserved.