2-(4-benzyloxyphenyl)ethyl tosylate | 86587-62-4

• 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: 2-(4-benzyloxyphenyl)ethyl tosylate
• 英文别名: 2-(4'-benzyloxy)phenethyl-p-methylbenzenesulfonate；2-(4-Benzyloxyphenyl)ethanol tosylate；2-(4-phenylmethoxyphenyl)ethyl 4-methylbenzenesulfonate
• CAS: 86587-62-4
• 化学式: C₂₂H₂₂O₄S
• 分子量: 382.48
• InChiKey: GBKAQYPBUBVGJM-UHFFFAOYSA-N

物化性质

• 沸点：
  553.8±38.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 氯仿 、 丙酮 为溶剂， 反应 21.0h， 生成 2-(4-benzyloxyphenyl)ethyl tosylate
  参考文献：
  名称：

  Head-to-tail connected double calix[4]arenes

  摘要：

  New macrotricyclic compounds consisting of two calix[4]arene substructures connected by aliphatic chains of various length (three to five carbon atoms) between two opposite p-positions and two distal phenolic oxygens have been synthesized. Starting with p-tert-butyl-calix[4] arene, two O-protected phenolic units are attached via ether links in 1,3-position by reaction with the corresponding tosylates. After deprotection, the new calix[4]arene is formed by fragment condensation with 2,6-bisbromomethylated 4-alkylphenols. The structure of one example (8c) has been confirmed by single crystal X-ray analysis. Both calixarene parts assume the cone conformation, a molecule of acetonitrile being included in both cavities.

  DOI：

  10.1007/bf00807096

文献信息

• Heterocycles as masked diamide/dipeptide equivalents. Formation and reactions of substituted 5-(acylamino)oxazoles as intermediates en route to the cyclopeptide alkaloids
  作者：Bruce H. Lipshutz、Randall W. Hungate、Keith E. McCarthy

  DOI：10.1021/ja00364a041

  日期：1983.12

  Etude de la synthese de dialkyl-2,4 acylamino-5 oxazoles par cyclisation a partir d'α-cyanoalkylamides d'acides, de N-acetyl α-aminoamides ou de dipeptides. Fonctionnalisation des oxazoles obtenus

  从二烷基-2,4 酰基氨基-5 恶唑环化到部分 d'α-氰基烷基酰胺 d'酸、去 N-乙酰 α-氨基酰胺或二肽合成练习曲。钝性恶唑功能化
• 3-Phenoxypropan-2-ol derivatives for treating glaucoma
  申请人：Synthelabo

  公开号：US04515814A1

  公开（公告）日：1985-05-07

  New 3-phenoxypropan-2-ol derivatives of the formula: ##STR1## wherein R represents a cycloalkyl radical having 5 or 6 carbon atoms, X represents an oxygen atom or a bond, and R' represents the isopropyl or tert.-butyl radical, have been found to be useful in therapy, and more particularly in the treatment of cardiovascular diseases and glaucoma.

  新的3-苯氧基丙烷-2-醇衍生物的化学式如下：##STR1## 其中R代表含有5或6个碳原子的环烷基基团，X代表氧原子或键，R'代表异丙基或叔丁基基团，已发现在治疗中具有用途，尤其是在心血管疾病和青光眼的治疗中。
• An approach to the cyclopeptide alkaloids (phencyclopeptines) via heterocyclic diamide/dipeptide equivalents. Preparation and N-alkylation studies of 2,4(5)-disubstituted imidazoles
  作者：Bruce H. Lipshutz、Matthew C. Morey

  DOI：10.1021/jo00169a027

  日期：1983.10
• Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique
  申请人：SYNTHELABO

  公开号：EP0074873B1

  公开（公告）日：1984-11-21
• US4515814A
  申请人：——

  公开号：US4515814A

  公开（公告）日：1985-05-07