(2-bromoethyl)(2-fluorophenyl)sulfane | 333782-41-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-bromoethyl)(2-fluorophenyl)sulfane
• 英文别名: 1-(2-Bromoethylsulfanyl)-2-fluorobenzene
• CAS: 333782-41-5
• 化学式: C₈H₈BrFS
• 分子量: 235.12
• InChiKey: NRBMYQQQLYUQTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-bromoethyl)(2-fluorophenyl)sulfane 、 berberrubine 以 乙腈 为溶剂， 反应 16.0h， 以35%的产率得到9-O-[2-(o-fluoro)thiophenyl]ethyl-berberine bromide
  参考文献：
  名称：

  Synthesis and biological evaluation of berberine–thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity

  摘要：

  A series of berberine-thiophenyl hybrids were designed, synthesised, and evaluated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and beta-amyloid (A beta) aggregation and as antioxidants. Among these hybrids, compounds 4f and 4i, berberine linked with o-methylthiophenyl and o-chlorothiophenyl by a 2-carbon spacer, were observed to be potent inhibitors of AChE, with IC50 values of 0.077 and 0.042 mu M, respectively. Of the tested compounds, 4i was also the most potent inhibitor of BuChE, with an IC50 value of 0.662 mu M. Kinetic studies and molecular modelling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine. derivatives. The biological studies also demonstrated that these hybrids displayed interesting activities, including A beta aggregation inhibition and antioxidant properties. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.011
• 作为产物：
  描述：

  2-氟苯硫酚 、 1,2-二溴乙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以52.1%的产率得到(2-bromoethyl)(2-fluorophenyl)sulfane
  参考文献：
  名称：

  硫醚桥联的芳烷基连接的N-苯基吡唑衍生物：设计，合成，杀虫活性，结构-活性关系和分子模型研究

  摘要：

  由于硫醚通过与生物大分子的非共价相互作用而具有多种理化特性，因此含有杂环部分的硫醚衍生物以其有趣的杀虫生物活性而闻名，并作为神经活性杀虫剂引起了广泛关注。在这里，我们合成了一系列新颖的硫醚桥联的N-苯基吡唑衍生物，这些衍生物在吡唑环的4位上掺入了各种（杂）芳族取代基。结构活性关系（SAR）研究表明，化合物6d和7d在含有各种取代苯取代基的系列中具有最强的杀虫活性（LC 50 = 13.70–25.47μg/ g）。进一步优化以增加化合物6d和7d的芳香族取代基的亲脂性和电荷密度，导致化合物12d，14d和16d中具有含硫杂环取代基的化合物对家蝇具有良好的杀虫活性（LC 50  = 0.67-1.30微克/克）。硫醚桥N-苯基吡唑衍生物，在N之间引入不同的间隔臂长度还制备并评价了-苯基吡唑部分和（杂）芳族取代基。相比之下，含有短硫醚桥的1,2-双（（杂）芳硫代）乙烷的化合物的杀虫活性高于含有长硫醚桥1

  DOI：

  10.1016/j.bmcl.2018.04.022

文献信息

• Quinolylpropylpiperidine derivatives, their preparation and the compositions which comprise them
  申请人：Aventis Pharma S.A.

  公开号：US06403610B1

  公开（公告）日：2002-06-11

  Quinolylpropylpiperidine derivatives of formula (I) which are particularly advantageous antimicrobial agents, their compositions, and their use.

  配方（I）的喹诺啉丙基哌啶衍生物，特别有优势的抗微生物药剂，其组成成分和用途。
• DERIVES DE LA QUINOLYL PROPYL PIPERIDINE ET LEUR UTILISATION EN TANT QUE ANTIBACTERIENS
  申请人：Aventis Pharma S.A.

  公开号：EP1218370A2

  公开（公告）日：2002-07-03
• US6403610B1
  申请人：——

  公开号：US6403610B1

  公开（公告）日：2002-06-11
• [EN] PIPERIDINE QUINOLYL PROPYL DERIVATIVES, PREPARATION METHOD AND COMPOSITIONS CONTAINING SAME<br/>[FR] DERIVES DE LA QUINOLYL PROPYL PIPERIDINE, LEUR PREPARATION ET LES COMPOSITIONS QUI LES CONTIENNENT
  申请人：AVENTIS PHARMA SA

  公开号：WO2001025227A2

  公开（公告）日：2001-04-12

  Un dérivés de quinolyl propyl pipéridine de formule générale (I) dans laquelle R1 est une atome d'hydrogène ou d'halogène, ou un radical hydroxy, R'1 est un atome d'hydrogène, ou peut représenter halogène lorsque R1 est également un atome d'halogène, et Ro est un atome d'hydrogène. Ces dérivés sont des agents antimicrobiens.
• Synthesis and biological evaluation of berberine–thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity
  作者：Tao Su、Shishun Xie、Hui Wei、Jun Yan、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2013.07.011

  日期：2013.9

  A series of berberine-thiophenyl hybrids were designed, synthesised, and evaluated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and beta-amyloid (A beta) aggregation and as antioxidants. Among these hybrids, compounds 4f and 4i, berberine linked with o-methylthiophenyl and o-chlorothiophenyl by a 2-carbon spacer, were observed to be potent inhibitors of AChE, with IC50 values of 0.077 and 0.042 mu M, respectively. Of the tested compounds, 4i was also the most potent inhibitor of BuChE, with an IC50 value of 0.662 mu M. Kinetic studies and molecular modelling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine. derivatives. The biological studies also demonstrated that these hybrids displayed interesting activities, including A beta aggregation inhibition and antioxidant properties. (C) 2013 Elsevier Ltd. All rights reserved.