methyl benzofuran-2-carbimididate hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl benzofuran-2-carbimididate hydrochloride
• 英文别名: methyl benzofurancarboximidate hydrochloride；methyl benzofuran-2-carboximidate hydrochloride；Methyl benzofuran-2carboximidate hydrochloride；methyl 1-benzofuran-2-carboximidate;hydrochloride
• 化学式: C₁₀H₉NO₂*ClH
• 分子量: 211.648
• InChiKey: KKNYTPLDNOTPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl benzofuran-2-carbimididate hydrochloride 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 33.25h， 生成 1-ethyl-2-(benzofuran-2-yl)-1H-imidazole hydrochloride
  参考文献：
  名称：

  Benzofuranyl-2-imidazoles as imidazoline I2 receptor ligands for Alzheimer's disease

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113540
• 作为产物：
  描述：

  苯并呋喃-2-甲腈 以 甲醇 、 ethereal HCl 为溶剂， 生成 methyl benzofuran-2-carbimididate hydrochloride
  参考文献：
  名称：

  Benzofuranylimidazole derivatives, a process for their preparation and

  摘要：

  该发明涉及一般式（1）的苯并呋喃基咪唑衍生物，其中R.sub.1和R.sub.2代表各种基团，以及它们的制备方法和含有它们的药物组合物。

  公开号：

  US05310930A1

文献信息

• Benzofuranylimidazole derivatives and therapeutical compositions
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques

  公开号：US05354769A1

  公开（公告）日：1994-10-11

  The invention relates to benzofuranylimidazole derivatives of the general formula (1) ##STR1## wherein R.sub.1 and R.sub.2 represent various radicals, to a process for their preparation and to pharmaceutical compositions containing them.

  本发明涉及一种通式（1）的苯并呋喃基咪唑衍生物，其中R.sub.1和R.sub.2代表各种基团，以及制备它们的方法和含有它们的制药组合物。
• Docking studies of benzylidene anabaseine interactions with α7 nicotinic acetylcholine receptor (nAChR) and acetylcholine binding proteins (AChBPs): Application to the design of related α7 selective ligands
  作者：David C. Kombo、Anatoly Mazurov、Kartik Tallapragada、Philip S. Hammond、Joseph Chewning、Terry A. Hauser、Montserrat Vasquez-Valdivieso、Daniel Yohannes、Todd T. Talley、Palmer Taylor、William S. Caldwell

  DOI：10.1016/j.ejmech.2011.09.033

  日期：2011.11

  AChBPs isolated from Lymnaea stagnalis (Ls), Aplysia californica (Ac) and Bulinus truncatus (Bt) have been extensively used as structural prototypes to understand the molecular mechanisms that underlie ligand-interactions with nAChRs [1]. Here, we describe docking studies on interactions of benzylidene anabaseine analogs with AChBPs and alpha 7 nAChR. Results reveal that docking of these compounds using Glide software accurately reproduces experimentally-observed binding modes of DMXBA and of its active metabolite, in the binding pocket of Ac. In addition to the well-known nicotinic pharmacophore (positive charge, hydrogen-bond acceptor, and hydrophobic aromatic groups), a hydrogen-bond donor feature contributes to binding of these compounds to Ac. Bt, and the alpha 7 nAChR. This is consistent with benzylidene anabaseine analogs with OH and NH2 functional groups showing the highest binding affinity of these congeners, and the position of the ligand shown in previous X-ray crystallographic studies of ligand-Ac complexes. In the predicted ligand-Ls complex, by contrast, the ligand OH group acts as hydrogen-bond acceptor. We have applied our structural findings to optimizing the design of novel spirodiazepine and spiroimidazoline quinuclidine series. Binding and functional studies revealed that these hydrogen-bond donor containing compounds exhibit improved affinity and selectivity for the alpha 7 nAChR subtype and demonstrate partial agonism. The gain in affinity is also due to conformational restriction, tighter hydrophobic enclosures, and stronger cation-pi interactions. The use of AChBPs structure as a surrogate to predict binding affinity to alpha 7 nAChR has also been investigated. On the whole, we found that molecular docking into Ls binding site generally scores better than when a alpha 7 homology model, Bt or Ac crystal structure is used. (C) 2011 Elsevier Masson SAS. All rights reserved.
• US5310930A
  申请人：——

  公开号：US5310930A

  公开（公告）日：1994-05-10
• US5354769A
  申请人：——

  公开号：US5354769A

  公开（公告）日：1994-10-11
• Benzofuranyl-2-imidazoles as imidazoline I2 receptor ligands for Alzheimer's disease
  作者：Sergio Rodriguez-Arévalo、Andrea Bagán、Christian Griñán-Ferré、Foteini Vasilopoulou、Mercè Pallàs、Iria Brocos-Mosquera、Luis F. Callado、M. Isabel Loza、Antón L. Martínez、José Brea、Belén Pérez、Elies Molins、Steven De Jonghe、Dirk Daelemans、Milica Radan、Teodora Djikic、Katarina Nikolic、Elena Hernández-Hernández、M. Julia García-Fuster、Jesús A. García-Sevilla、Carmen Escolano

  DOI：10.1016/j.ejmech.2021.113540

  日期：2021.10