2-((4-methoxyphenyl)(phenylthio)methyl)pyridine | 1384458-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxyphenyl)(phenylthio)methyl)pyridine
• 英文别名: 2-[(4-Methoxyphenyl)-phenylsulfanyl-methyl]pyridine；2-[(4-methoxyphenyl)-phenylsulfanylmethyl]pyridine
• CAS: 1384458-15-4
• 化学式: C₁₉H₁₇NOS
• 分子量: 307.416
• InChiKey: BAKYBMYWHFHAPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-甲氧基苯基溴化镁 以 四氢呋喃 、 苯 为溶剂， 反应 1.5h， 生成 2-((4-methoxyphenyl)(phenylthio)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

• Friedel–Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: an easy access to pyridyl aryl/heteroaryl carbinols
  作者：Adhikesavan Harikrishnan、Jayaraman Selvakumar、Elumalai Gnanamani、Suman Bhattacharya、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c2nj40871f

  日期：——

  Aromatic electrophilic substitution of aromatic/electron rich heteroaromatic compounds with AlBr3 activated aldehydes/ketone to afford pyridyl aryl/heteroaryl or diaryl carbinols is described. The strong electron donating group dictates the regiochemical outcome of the product.

  描述了芳香族/电子丰富的杂芳香化合物与AlBr3激活的醛/酮进行芳香电亲核取代反应，以获得吡啶基芳香烃/杂芳烃或二芳基碳醇。强电子给体基团决定了产物的区位化学结果。