3-[(5-phenyl-thiophen-2-ylmethyl)amino]adamantan-1-ol | 1443123-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-[(5-phenyl-thiophen-2-ylmethyl)amino]adamantan-1-ol
• 英文别名: 3-[(5-Phenylthiophen-2-yl)methylamino]adamantan-1-ol
• CAS: 1443123-25-8
• 化学式: C₂₁H₂₅NOS
• 分子量: 339.502
• InChiKey: OCWASHBKIUTDNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-胺基-1-金刚烷醇 在 四(三苯基膦)钯 、 titanium(IV)isopropoxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.17h， 生成 3-[(5-phenyl-thiophen-2-ylmethyl)amino]adamantan-1-ol
  参考文献：
  名称：

  Structure–Property Relationship Studies of Influenza A Virus AM2-S31N Proton Channel Blockers

  摘要：

  Majority of current circulating influenza A viruses carry the S31N mutation in their M2 genes, rendering AM2-531N as a high profile antiviral drug target. With our continuous interest in developing AM2-531N channel blockers as novel antivirals targeting both oseltamivir-sensitive and -resistant influenza A viruses, we report herein the structure-property relationship studies of AM2-S31N inhibitors. The goal was to identify lead compounds with improved microsomal stability and membrane permeability. Two lead compounds, 10d and 10e, were found to have high mouse and human liver microsomal stability (T-1/2, > 145 min) and membrane permeability (> 200 nm/s). Both compounds also inhibit both currently circulating oseltamivir-sensitive and-resistant human influenza A viruses (H1N1 and H3N2) with EC50 values ranging from 0.4 to 2.8 mu M and a selectivity index of > 100. We also showed for the first time that AM2-S31N channel blockers such as 10e inhibited influenza virus replication at both low and high multiply of infection (10(2)-10(6) pfu/mL) and the inhibition was not cell-type dependent. Overall, these studies have identified two promising lead candidates for further development as antiviral drugs against drug-resistant influenza A viruses.

  DOI：

  10.1021/acsmedchemlett.8b00336

文献信息

• [EN] INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A<br/>[FR] INHIBITEURS CIBLANT LA GRIPPE A PHARMACORÉSISTANTE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2013086131A1

  公开（公告）日：2013-06-13

  Provided are compounds according to formula (la) or (lb) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (la') or (lb), as described herein.

  根据本文描述的公式（la）或（lb），提供了一些化合物，这些化合物能够调节流感病毒（例如流感A病毒）的活性，例如通过与M2跨膜蛋白以及其他类似的病毒孔蛋白相互作用。还提供了一种治疗流感A感染疾病状态或感染的方法，包括通过给予包含根据本文描述的公式（la'）或（lb）的一个或多个化合物的组合物进行治疗。
• INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US20150191439A1

  公开（公告）日：2015-07-09

  Provided are compounds according to formula (Ia) or (Ib) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (Ia′) or (Ib), as described herein.

  提供了符合公式（Ia）或（Ib）的化合物，可以通过与M2跨膜蛋白和其他类似的病毒孔蛋白相互作用，调节流感病毒（例如流感A病毒）的活性。还提供了一种治疗流感A受影响的疾病状态或感染的方法，包括给予含有一个或多个符合公式（Ia′）或（Ib）的化合物的组合物。
• US9884832B2
  申请人：——

  公开号：US9884832B2

  公开（公告）日：2018-02-06