1,14-bis(imidazole)tetradecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,14-bis(imidazole)tetradecane
• 英文别名: 1,14-bis-(1H-imidazol-1-yl)tetradecane；1-(14-Imidazol-1-yltetradecyl)imidazole
• 化学式: C₂₀H₃₄N₄
• 分子量: 330.517
• InChiKey: AMBNKGLMPDTHLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,14-bis(imidazole)tetradecane 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  通过环的末端炔偶联反应：环大小对速率和区域选择性的影响。

  摘要：

  由基于大环 NHC 的钳形配体的铑 (I) 配合物促进的末端炔烃偶联反应，其特征是十二亚甲基、十四亚甲基或十六亚甲基翼尖连接体，即。[Rh(CNC-n)(C 2 H 4 )][BAr F 4 ] (n=12, 14, 16; Ar F =3,5-(CF 3 ) 2 C 6 H 3 )—已被研究，使用大炔烃 HC≡C t Bu 和 HC≡CAr' (Ar'=3,5‐ t Bu 2 C 6 H 3 ) 作为底物。这些化学计量反应继续形成铑(III)炔基烯基衍生物，并通过辅助配体的环通过CC键还原消除产生共轭1,3-烯炔的铑(I)络合物。中间体以正交区域选择性形成，其中E-烯基配合物衍生自HC≡C t Bu，gem-烯基配合物衍生自HC≡CAr'，并且还原消除步骤明显受到大环环尺寸的影响。对于 HC−C t Bu的自偶联，E ‐ t BuC−CCH=CH t Bu 是通过相应的铑 (III) 炔基E

  DOI：

  10.1002/chem.202002962
• 作为产物：
  描述：

  1,14-二溴十四烷 、 咪唑钠 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,14-bis(imidazole)tetradecane
  参考文献：
  名称：

  Bis-imidazoles as molecular probes for peripheral sites of the zinc endopeptidase of botulinum neurotoxin serotype A

  摘要：

  Botulinum neurotoxin serotype A (BoNTA) is highly toxic, and its antidote is currently unavailable. The essential light-chain subunit of BoNTA is a zinc endopeptidase that can be used as a target for developing antidotes. However, the development of high-affinity, small-molecule inhibitors of the endopeptidase is as challenging as the development of small-molecule inhibitors of protein-protein complexation. This is because the polypeptide substrate wraps around the circumference of the endopeptidase upon binding, thereby constituting an unusually large substrate-enzyme interface of 4840 angstrom(2). To overcome the large-interface problem, we propose using the zinc-coordination and bivalence approaches to design inhibitors of BoNTA. Here we report the development of alkylene-linked bis-imidazoles that inhibit the endopeptidase in a two-site binding mode, The bis-imidazole tethered with 13 methylene groups, the most potent of the alkylene-linked dimers, showed 61% inhibition of the zinc endopeptidase of BoNTA at a concentration of 100 mu M. The results demonstrate the presence of a peripheral binding site for an imidazolium group at the rim of the BoNTA active-site cleft. This peripheral site enables the use of the bivalence approach to improve Our previously reported small-molecule inhibitors that were developed according to the zinc-coordination approach. (c) 2006 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.015

文献信息

• TRIAZOLIUM AND IMIDAZOLIUM SALTS AND USES THEREOF
  申请人：Crandall Ian E.

  公开号：US20110257235A1

  公开（公告）日：2011-10-20

  The present disclosure relates to certain new and known triazolium and/or imidazolium salts and to their therapeutic use, for example in methods of treating or preventing an infection by a Plasmodium or Babesia parasite in a subject in need thereof. The triazolium and imidazolium salts are compounds of the Formula (I) or (II): wherein R 1 -R 4 , R 1′ -R 3′ , R 8 -R 11 , X, X′, X″, Y, Y′ and Y″ are as defined in the disclosure.

  本公开涉及某些新的和已知的三唑和/或咪唑盐及其治疗用途，例如在治疗或预防受需要的主体中由Plasmodium或Babesia寄生虫引起的感染的方法中。三唑和咪唑盐是以下化合物的化合物：其中R1-R4，R1′-R3′，R8-R11，X，X′，X″，Y，Y′和Y″如本公开所定义。
• The anti-malarial activity of bivalent imidazolium salts
  作者：Jason Z. Vlahakis、Simona Mitu、Gheorghe Roman、E. Patricia Rodriguez、Ian E. Crandall、Walter A. Szarek

  DOI：10.1016/j.bmc.2011.06.002

  日期：2011.11

  A series of compounds containing bivalent imidazolium rings and one triazolium analog were synthesized and evaluated for their ability to inhibit the replication of Plasmodium falciparum cultures. The activity and selectivity of the compounds for P. falciparum cultures were found to depend on the presence of electron-deficient rings that were spaced an appropriate distance apart. The activity of the compounds was not critically dependent on the nature of the linker between the electron-deficient rings, an observation that suggests that the rings were responsible for the primary interaction with the molecular target of the compounds in the parasite. The bivalent imidazolium and triazolium compounds disrupted the process whereby merozoites gain entry into erythrocytes, however, they did not appear to prevent merozoites from forming. The compounds were also found to be active in a murine Plasmodium berghei infection, a result consistent with the compounds specifically interacting with a parasite component that is required for replication and is conserved between two Plasmodium species. (C) 2011 Elsevier Ltd. All rights reserved.
• US8632914B2
  申请人：——

  公开号：US8632914B2

  公开（公告）日：2014-01-21