(4,4,4-trifluoromethyl-3-tert-butyldimethylsilyloxy)butyl p-tosylate | 1135467-48-9

• 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: (4,4,4-trifluoromethyl-3-tert-butyldimethylsilyloxy)butyl p-tosylate
• 英文别名: [3-[Tert-butyl(dimethyl)silyl]oxy-4,4,4-trifluorobutyl] 4-methylbenzenesulfonate
• CAS: 1135467-48-9
• 化学式: C₁₇H₂₇F₃O₄SSi
• 分子量: 412.546
• InChiKey: JCKYYXBYWLKFDK-UHFFFAOYSA-N

物化性质

• 沸点：
  420.6±45.0 °C(predicted)
• 密度：
  1.141±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-硝基亚氨基咪唑烷 、 (4,4,4-trifluoromethyl-3-tert-butyldimethylsilyloxy)butyl p-tosylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 生成 1-[(4,4,4-trifluoro-3-tert-butyldimethylsilyloxy)butyl]-2-nitroiminoimidazolidine
  参考文献：
  名称：

  Neonicotinoid Substituents Forming a Water Bridge at the Nicotinic Acetylcholine Receptor

  摘要：

  Neonicotinoid insecticides are extensively used for crop protection. The chloropyridinyl or chlorothiazolyl nitrogen and tetrahydrofuryl oxygen atoms of neonicotinoids serve as hydrogen acceptors at the target site. This investigation designs and prepares neonicotinoid probes to understand the structure-activity relationships (SARs) at the target site focusing on the water-mediated ligand-protein interactions. 2-Nitroiminoimidazolidine analogues with hydrogen-acceptor N-CH2CH2CH2F and N-CH2CH2C(O)CH3 substituents showed higher binding affinities to the Drosophila melanogaster nicotinic receptor than probes with different hydrogen-bonding points in location and capability, suggesting that the appropriately positioned fluorine or carbonyl oxygen plays an important role on hydrogen-bond formation. Their binding site interactions were predicted using a crystal structure of the acetylcholine binding protein. The fluorine or carbonyl oxygen forms a water bridge to Ile-118 (and/or Ile-106) at the binding domain, consistent with that of neonicotinoids with a chloropyridinylmethyl, chlorothiazolylmethyl, or tetrahydrofurylmethyl moiety. Therefore, the present SAR study on binding site interactions helps design potent neonicotinoids with novel substituents.

  DOI：

  10.1021/jf803985r

文献信息

• [EN] CONJUGATE COMPRISING TOLL-LIKE RECEPTOR AGONIST<br/>[FR] CONJUGUÉ COMPRENANT UN AGONISTE DU RÉCEPTEUR DE TYPE TOLL
  申请人：[en]MABSOFT THERAPEUTICS (SHANGHAI) CO., LTD.

  公开号：WO2023198195A1

  公开（公告）日：2023-10-19

  Disclosed herein are compounds that are Toll-like receptor (TLR) agonist, conjugates comprising these compounds and cell targeting moiety, pharmaceutical compositions thereof, method of activating toll-like receptors 7 and/or 8 and method for the treatment of diseases or disorders mediated by toll-like receptors 7 and/or 8, in particular viral infections and proliferative disorders, such as cancer.
• Neonicotinoid Substituents Forming a Water Bridge at the Nicotinic Acetylcholine Receptor
  作者：Ikuya Ohno、Motohiro Tomizawa、Kathleen A. Durkin、John E. Casida、Shinzo Kagabu

  DOI：10.1021/jf803985r

  日期：2009.3.25

  Neonicotinoid insecticides are extensively used for crop protection. The chloropyridinyl or chlorothiazolyl nitrogen and tetrahydrofuryl oxygen atoms of neonicotinoids serve as hydrogen acceptors at the target site. This investigation designs and prepares neonicotinoid probes to understand the structure-activity relationships (SARs) at the target site focusing on the water-mediated ligand-protein interactions. 2-Nitroiminoimidazolidine analogues with hydrogen-acceptor N-CH2CH2CH2F and N-CH2CH2C(O)CH3 substituents showed higher binding affinities to the Drosophila melanogaster nicotinic receptor than probes with different hydrogen-bonding points in location and capability, suggesting that the appropriately positioned fluorine or carbonyl oxygen plays an important role on hydrogen-bond formation. Their binding site interactions were predicted using a crystal structure of the acetylcholine binding protein. The fluorine or carbonyl oxygen forms a water bridge to Ile-118 (and/or Ile-106) at the binding domain, consistent with that of neonicotinoids with a chloropyridinylmethyl, chlorothiazolylmethyl, or tetrahydrofurylmethyl moiety. Therefore, the present SAR study on binding site interactions helps design potent neonicotinoids with novel substituents.