2-<2-Benzyloxy-5-methoxy-phenyl>-aethylamin | 74516-59-9

• 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-<2-Benzyloxy-5-methoxy-phenyl>-aethylamin
• 英文别名: 2-(5-Methoxy-2-phenylmethoxyphenyl)ethanamine
• CAS: 74516-59-9
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: UPPFDZBHJOPNAI-UHFFFAOYSA-N

物化性质

• 沸点：
  402.6±35.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-Benzyloxy-5-methoxy-phenyl>-aethylamin 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.5h， 生成 N-benzyl-N-(ethoxymethyl)-2-(5-methoxy-2-phenylmethoxyphenyl)ethanamine
  参考文献：
  名称：

  A Facile Synthesis of 1,2,3,4-Tetrahydroisoquinolines Through Cyclization ofO,N-Acetals

  摘要：

  本论文介绍了一种通过改良的 Pictet-Spengler 反应合成 1,2,3,4-四氢异喹啉的温和而高效的方法，该反应涉及路易斯酸介导的 O,N-乙醛环化。

  DOI：

  10.1055/s-1987-28089
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 在 lithium aluminium tetrahydride 、 ammonium acetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 34.0h， 生成 2-<2-Benzyloxy-5-methoxy-phenyl>-aethylamin
  参考文献：
  名称：

  [d4U]-butyne-[HI-236] as a non-cleavable, bifunctional NRTI/NNRTI HIV-1 reverse-transcriptase inhibitor

  摘要：

  The synthesis of bifunctional compound 10 consisting of d4U joined at C-5 to a butynyl spacer attached to HI-236 is reported using a Sonogashira coupling as a key step. As a non-cleavable bifunctional HIV inhibitor incorporating an NRTI with an NNRTI, 10 shows good inhibitory activity (EC50 = 250 nM) against HIV (IIIB) replication in NIT-2 cell culture, which is eight times greater than that of d4T and between those of the two component drugs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.107

文献信息

• [d4U]-Spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase
  作者：Yassir Younis、Roger Hunter、Clare I. Muhanji、Ian Hale、Rajinder Singh、Christopher M. Bailey、Todd J. Sullivan、Karen S. Anderson

  DOI：10.1016/j.bmc.2010.05.025

  日期：2010.7

  propargyl-4-PEG (15d) have been synthesized and biologically evaluated as RT inhibitors against HIV-1. The key step in their synthesis involved a Sonogashira coupling of 5-iodo d4U’s benzoate with an alkynylated tethered HI-236 precursor followed by introduction of the HI-236 thiourea functionality. Biological evaluation in both cell-culture (MT-2 cells) as well as using an in vitro RT assay revealed 15a–c to

  [d4U]-间隔基-[HI-236] 类型的四种双药 HIV NRTI/NNRTI 抑制剂15a – d，其中间隔基变化为 1-丁炔基 ( 15a )、炔丙基-1-PEG ( 15b )、炔丙基-2-PEG ( 15c ) 和炔丙基-4-PEG ( 15d ) 已被合成并作为抗 HIV-1 的 RT 抑制剂进行生物学评估。他们合成的关键步骤涉及 5-碘 d4U 苯甲酸酯与炔基化 HI-236 前体的 Sonogashira 偶联，然后引入 HI-236 硫脲官能团。细胞培养（MT-2 细胞）以及使用体外 RT 测定的生物学评估显示15a – c比 d4T 更活跃。然而，总体而言，结果表明衍生物作为链延长的 NNRTIs，其中对于15b - d，核苷组分可能位于口袋外，但没有证据表明 NRTI 和 NNRTI 位点之间存在任何协同双结合。这部分归因于由于激酶识别失败导致双药核苷组分缺乏磷酸化，而结合
• The Partial O-Demethylation of Aromatic-Substituted 3,4-Dihydroisoquinolines
  作者：A. Brossi、S. Teitel

  DOI：10.1002/hlca.19700530726

  日期：——

  A detailed study has shown that all possible aromatic dimethoxy-substituted 3,4-dihydroisoquinolines can be partially O-demethylated by controlled acid hydrolysis. Based on the structure elucidation of the monophenols thus obtained, it was established that preferential cleavage occurs at the 5-methoxyl with the 5,6- and 5,8-isomers 1 and 3, respectively, at the 6-methoxyl with the 6,8-isomer 4, at

  一项详细的研究表明，所有可能的芳香族二甲氧基取代的3,4-二氢异喹啉都可以通过受控的酸水解部分进行O-去甲基化。基于由此获得的单酚的结构阐明，确定了优先裂解发生在分别具有5,6-和5,8-异构体1和3的5-甲氧基处，发生于具有6、6的6-甲氧基的优先裂解处。 8-异构体4，在7-甲氧基与5,7-异构体5，和在8-甲氧基与7,8-异构体2。
• 1,2,3,4-tetrahydroisoquinoline derivatives
  申请人：——

  公开号：US20030176415A1

  公开（公告）日：2003-09-18

  The invention relates to novel 1,2,3,4-tetrahydroisochinoline derivatives of formula (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.

  本发明涉及新型1,2,3,4-四氢异喹啉衍生物的公式（I），以及它们作为药物组分在制备药物组合物中的使用。本发明还涉及相关方面，包括制备该化合物的过程，含有其中一种或多种化合物的药物组合物，特别是它们作为促进睡眠的药物组分。
• C-2-Aryl O-substituted HI-236 derivatives as non-nucleoside HIV-1 reverse-transcriptase inhibitors
  作者：Roger Hunter、Yassir Younis、Clare I. Muhanji、Tanith-lea Curtin、Kevin J. Naidoo、Melissa Petersen、Christopher M. Bailey、Aravind Basavapathruni、Karen S. Anderson

  DOI：10.1016/j.bmc.2008.10.048

  日期：2008.12.15

  Several novel thiourea derivatives of the NNRTI HI-236 substituted at the C-2 oxygen of the phenyl ring have been synthesized and evaluated for their inhibitory activity against HIV-1 ( IIIB) replication in MT-2 cell cultures. The compounds were synthesized in order to fine-tune the activity of HI-236 as well as to gain insight into spatial characteristics in the pocket pertaining to the positional choice of tether in the design of [NRTI]-tether-[HI-236] bifunctional inhibitors. Two of the thiourea derivatives bearing a butynyl (6c) or hydroxyethyl tether (6n) were endowed with improved anti-HIV activity compared to HI-236. NNRTI activity was confirmed by a cell-free RT assay on six of the derivatives in which 6c returned an IC50 of 3.8 nM compared to 28 nM for HI-236, establishing it as an improved lead for HI-236. The structure-activity pro. le is discussed in terms of potential interactions in the NNRTI pocket as suggested by a docking model using AutoDock, which have a bearing on the bifunctional drug design. (C) 2008 Elsevier Ltd. All rights reserved.
• GLENNON R. A.; LIEBOWITZ S. M.; LEMING-DOOT D.; ROSECRANS J. A., J. MED. CHEM., 1980, 23, NO 9, 990-994
  作者：GLENNON R. A.、 LIEBOWITZ S. M.、 LEMING-DOOT D.、 ROSECRANS J. A.

  DOI：——

  日期：——