1-(3-叠氮丙基)-4-甲氧基苯 | 583825-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(3-叠氮丙基)-4-甲氧基苯
• 英文名称: 1-(3-azidopropyl)-4-methoxybenzene
• 英文别名: 3-(4-Methoxyphenyl)propylazide；(4-methoxyphenyl)propylazide
• CAS: 583825-29-0
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: UDIBAKKSJQBIEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 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：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-叠氮丙基)-4-甲氧基苯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-(4-甲氧基苯基)-丙胺
  参考文献：
  名称：

  醛基酮还原酶1B10的有效和选择性抑制剂的合成及其对肺癌细胞增殖，转移和顺铂耐药性的作用

  摘要：

  醛固酮还原酶1B10（AKR1B10）在几种肠外癌症中过度表达，尤其是在非小细胞肺癌中，其中AKR1B10是潜在的诊断标志物和治疗靶标。需要选择性的AKR1B10抑制剂，因为化合物不应抑制与单糖和前列腺素代谢有关的高度相关的醛糖还原酶。目前，7-羟基-2-（4- methoxyphenylimino）-2- ħ色烯-3-羧酸苄基酰胺（HMPC）已知是AKR1B10的最有效的竞争性抑制剂，但它是非选择性的。在这项研究中，HMPC的衍生物是通过除去4-甲氧基苯基亚氨基部分并将苄基酰胺替换为苯丙基酰胺而合成的。其中4c和4e与HMPC相比，AKR1B10具有更高的AKR1B10抑制能力（分别为IC 50 4.2和3.5 nM）和选择性。用这两种化合物进行的治疗不仅显着抑制了肺癌A549细胞的迁移，增殖和转移，而且显着抑制了对顺铂耐药的A549细胞的转移和侵袭潜能。

  DOI：

  10.1021/acs.jmedchem.7b00830
• 作为产物：
  描述：

  1-甲磺酰氧基-3-(4-甲氧基苯基)丙烷 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(3-叠氮丙基)-4-甲氧基苯
  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

• Site‐Selective Alkoxylation of Benzylic C−H Bonds by Photoredox Catalysis
  作者：Byung Joo Lee、Kimberly S. DeGlopper、Tehshik P. Yoon

  DOI：10.1002/anie.201910602

  日期：2020.1.2

  strategies for C-N and C-C bond formation. In particular, almost all methods for the incorporation of alcohols by C-H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C-H bonds with a wide range of oxygen

  特别是与CN和CC键形成的类似策略相比，能够使复杂有机分子直接进行CH烷氧基化的方法还远远不够。特别地，几乎所有用于通过CH氧化引入醇的方法都需要使用醇组分作为溶剂或助溶剂。该条件将这些反应的实际范围限制为简单，廉价的醇。此处报道的是一种光催化方案，用于使用多种氧亲核试剂对苄基CH键进行官能化。此策略将芳烃的光氧化还原活化与铜（II）介导的所得苄基自由基的氧化合并，从而可以高位点选择性，化学选择性，高选择性地引入苄基CO键，仅使用两当量的醇偶合剂就可以实现对官能团和官能团的耐受。这种方法可以将复杂的烷氧基后期引入生物活性分子中，提供了一种实用的新工具，在合成和药物化学中具有潜在的应用前景。
• Sodium channel blockers
  申请人：CYFI, INC.

  公开号：US20030195160A1

  公开（公告）日：2003-10-16

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂进行治疗的各种方法。
• Methods of using phenolic guanidine sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040198744A1

  公开（公告）日：2004-10-07

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂的各种治疗方法。
• Phenolic guanidine sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040204424A1

  公开（公告）日：2004-10-14

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂的各种治疗方法。
• Development of Dual-Acting Agents for Thromboxane Receptor Antagonism and Thromboxane Synthase Inhibition. 3. Synthesis and Biological Activities of Oxazolecarboxamide-Substituted ω-Phenyl-ω-(3-pyridyl)alkenoic Acid Derivatives and Related Compounds
  作者：Kumiko Takeuchi、Todd J. Kohn、Timothy A. True、Dale E. Mais、James H. Wikel、Barbara G. Utterback、Virginia L. Wyss、Joseph A. Jakubowski

  DOI：10.1021/jm980173n

  日期：1998.12.1

  A novel series of oxazolecarboxamide-substituted omega-phenyl-omega-(3-pyridyl)alkenoic acid derivatives was discovered as potent dual-acting agents to block the TXA(2) receptor and to inhibit the thromboxane synthase (TRA/TSI). Synthesis, structure-activity relationship (SAR), and in vitro and in vivo pharmacology of this series of compounds are described. Modification of the series revolved around the oxazole moiety to increase the hydrophilicity of the compounds and to correlate the biological activity with lipophilicity of the compounds. The most potent in the series was (E)-7-[4-[4-[[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid (14) with K-d = 9.9 +/- 0.4 nM for the thromboxane receptor antagonism and IC50 = 55.0 +/- 17.9 nM for thromboxane synthase inhibition. The compound 14 was a selective TRA/TSI which exhibited desirable characteristics for oral activity, "shunt" effect to elevate PGI(2) level, and absence of agonist activity.