2-[(p-methoxybenzyl)oxy]ethylamine | 40141-15-9

• 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-[(p-methoxybenzyl)oxy]ethylamine
• 英文别名: 2-[(4-Methoxyphenyl)methoxy]ethan-1-amine；2-[(4-methoxyphenyl)methoxy]ethanamine
• CAS: 40141-15-9
• 化学式: C₁₀H₁₅NO₂
• mdl: MFCD11147572
• 分子量: 181.235
• InChiKey: YNDFLZDLJHOLQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-[(p-methoxybenzyl)oxy]ethylamine 在 氯化铵 、 锌 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Acetyl-Click Screening Platform Identifies Small-Molecule Inhibitors of Histone Acetyltransferase 1 (HAT1)

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00039
• 作为产物：
  描述：

  2-(2-((4-Methoxybenzyl)oxy)ethyl)isoindoline-1,3-dione 在 甲胺 作用下， 以 甲醇 为溶剂， 以56%的产率得到2-[(p-methoxybenzyl)oxy]ethylamine
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis

  摘要：

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

  DOI：

  10.1021/jm051134w

文献信息

• Critical profiles of chiral diether-mediated asymmetric conjugate aminolithiation of enoate with lithium amide as a key to the total synthesis of (−)-kopsinine
  作者：Shingo Harada、Takeo Sakai、Kiyosei Takasu、Ken-ichi Yamada、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2013.02.035

  日期：2013.4

  with lithium amide in toluene at −78 °C for 15 min gave, after aqueous ammonium chloride quench, the corresponding conjugate addition product with 97% ee in 89% yield. If hydrogen chloride in methanol was selected as a quencher, however, aminolithiation at −78 °C for 3 h gave the corresponding adduct with 97% ee in 54% yield, along with recovery of the starting enoate in 39% yield. Based on this finding

  在-78°C条件下，在甲苯中于-78°C下用酰胺锂在丙烯中手性二醚介导的吲哚基丙酸酯与氨基酰胺的不对称氨基甲酸酯化反应，得到相应的共轭加成产物，其ee值为97％，收率为89％。但是，如果选择在甲醇中的氯化氢作为淬灭剂，则在-78°C进行3小时的氨基甲酰化反应可得到相应的加合物，其ee率为97％，收率为54％，同时回收了起始烯酸酯，收率为39％。基于在-78°C下反应不完全且反应缓慢的发现，将氨基锂化条件优化为在-60°C下放置15 h，随后在添加DMPU时用卤代烷捕获烯醇化物，得到了所需的氨基烷基化产物（98） ee百分含量为89％。通过检测不对称氨基甲硅烷基化反应，进一步实现了全合成（-）-kopsinine的方法。N-羟乙胺当量，一锅哌啶的形成，和克莱森缩合。
• Discovery of Novel Macrocyclic Hedgehog Pathway Inhibitors Acting by Suppressing the Gli-Mediated Transcription
  作者：Gang Liu、Wenjing Huang、Juan Wang、Xiaohua Liu、Jun Yang、Yu Zhang、Yong Geng、Wenfu Tan、Ao Zhang

  DOI：10.1021/acs.jmedchem.7b01185

  日期：2017.10.12

  several series of structurally unique tricyclic compounds. Among these, compound 29a was identified as the most potent against the Hedgehog (Hh) signaling pathway showing an IC50 value of 23 nM. Mechanism studies indicated that compound 29a inhibited the Hh signaling pathway by suppressing the expression of the transcriptional factors Gli rather than by interrupting the binding of Gli with DNA. We further

  通过载有两个侧基取代基的4,5-二氢-2 H-苯并[ b ] [1,5]恶唑啉-6（3 H）-一个核心的热门文献5进行了系统的药物化学研究结合N原子行走或环行走以及中心环扩展或提取方法的双环骨架结构，产生了一系列结构上独特的三环化合物。在这些化合物中，化合物29a被确定为对Hedgehog（Hh）信号通路最有效的化合物，IC 50值为23 nM。机制研究表明，化合物29a通过抑制转录因子Gli的表达而不是通过中断Gli与DNA的结合来抑制Hh信号通路。我们进一步观察到29a对Smo野生型和两个主要抗性突变体（Smo D473H和Smo W535L）均具有同等效力。在ptch±; p53 – / –髓母细胞瘤同种异体移植小鼠模型中，它有效抑制了髓母细胞瘤细胞的增殖并显示出显着的肿瘤生长抑制作用。尽管需要更多的研究来阐明29a与Gli的精确相互作用模式，但其有希望的体外和体内特性鼓励其作为新一
• Entry inhibition of hepatitis B virus using cyclosporin O derivatives with peptoid side chain incorporation
  作者：Dongjae Lee、Jung-Ah Kang、Chanseok Lim、Sunjae Bae、Jieun Choi、Minji Park、Yong-Chul Kim、Yuri Cho、Sung-Gyoo Park、Jiwon Seo

  DOI：10.1016/j.bmc.2022.116862

  日期：2022.8
• 2,5-DIOXOIMIDAZOLIDIN-1-YL-3-PHENYLUREA DERIVATIVES AS FORMYL PEPTIDE RECEPTOR LIKE-1 (FPRL-1) RECEPTOR MODULATORS
  申请人：ALLERGAN, INC.

  公开号：EP3103797B1

  公开（公告）日：2019-04-10
• US4259234A
  申请人：——

  公开号：US4259234A

  公开（公告）日：1981-03-31