1-叠氮基-2-(4-苄氧基苯基)乙烷 | 74447-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-叠氮基-2-(4-苄氧基苯基)乙烷
• 英文名称: 1-azido-2-(4-benzyloxyphenyl)ethane
• 英文别名: 1-(2'-azidoethyl)-4-(benzyloxy)benzene；1-(2-azidoethyl)-4-phenylmethoxybenzene
• CAS: 74447-33-9
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: MWRVPCFFPRPCGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.99
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-叠氮基-2-(4-苄氧基苯基)乙烷 在 盐酸 、 lithium aluminium tetrahydride 作用下， 生成 4-苄氧基-3-氨基-a-[-苄基-n-(1-甲基-2p-甲氧基苯酯) 氨基甲基苄醇
  参考文献：
  名称：

  Battersby; Chrystal; Staunton, Journal of the Chemical Society. Perkin transactions I, 1980, vol. 1, p. 31 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-benzyloxyphenyl)ethyl tosylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以96%的产率得到1-叠氮基-2-(4-苄氧基苯基)乙烷
  参考文献：
  名称：

  Tacrine-O-protected phenolics heterodimers as multitarget-directed ligands against Alzheimer's disease: Selective subnanomolar BuChE inhibitors

  摘要：

  Concerned by the devastating effects of Alzheimer's disease, and the lack of effective drugs, we have carried out the design of a series of tacrine-phenolic heterodimers in order to tackle the multifactorial nature of the disease.Hybridization of both pharmacophores involved the modification of the nature (imino, amino, ether) and the length of the tether, together with the type (hydroxy, methoxy, benzyloxy), number and position of the substituents on the aromatic residue. Title compounds were found to be strong and selective inhibitors of human BuChE (from low nanomolar to subnanomolar range), an enzyme that becomes crucial in the more advanced stages of the disease.The lead compound, bearing an ether-type tether, had an IC50 value of 0.52 nM against human BuChE, and a selectivity index of 323, with an 85-fold increase of activity compared to parent tacrine; key interactions were analysed using molecular modelling. Moreover, it also inhibited the self-aggregation of A beta 42, lacking neurotoxicity up to 5 mu M concentration, and showed neuroprotective activity in primary rat neurons in a serum and K+ deprivation model, widely employed for reproducing neuronal injury and senescence. Moreover, low hepatoxicity effects and complete stability under physiological conditions were found for that compound.So, overall, our lead compound can be considered as a promising multitarget-directed ligand against Alzheimer's disease, and a good candidate for developing new drugs. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.07.053

文献信息

• Non-urea functionality as the primary pharmacophore in soluble epoxide hydrolase inhibitors
  作者：Sampath-Kumar Anandan、Zung N. Do、Heather K. Webb、Dinesh V. Patel、Richard D. Gless

  DOI：10.1016/j.bmcl.2009.01.013

  日期：2009.2

  Inhibition of soluble epoxide hydrolase has been proposed as a promising new pharmaceutical target for diseases involving hypertension and vascular inflammation. The most potent sEH inhibitors reported to date contain a urea or amide moiety as the central or 'primary' pharmacophore. We evaluated replacing the urea pharmacophore with other functional groups such as thiourea, sulfonamide, sulfonylurea, aminomethylene amide, hydroxyamide, and ketoamide to identify novel and potent inhibitors. The hydroxyamide moiety was identified as a novel pharmacophore affording potency comparable to urea. (C) 2009 Elsevier Ltd. All rights reserved.