1-(2-(1H-indol-3-yl)ethyl)-3-(4-methoxyphenyl)urea | 16036-24-1

• 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: 1-(2-(1H-indol-3-yl)ethyl)-3-(4-methoxyphenyl)urea
• 英文别名: 1-[2-(1H-indol-3-yl)ethyl]-3-(4-methoxyphenyl)urea
• CAS: 16036-24-1
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: MYKYEGGYMNUGHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-(1H-indol-3-yl)ethyl)-3-(4-methoxyphenyl)urea 、 丁烯酮 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以81%的产率得到
  参考文献：
  名称：

  Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

  摘要：

  A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis Is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.

  DOI：

  10.1021/ol401039h
• 作为产物：
  描述：

  (1-Morpholin-4-ylmethyl-1H-indol-3-yl)-acetonitrile 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙醇 、 异丙醚 为溶剂， 生成 1-(2-(1H-indol-3-yl)ethyl)-3-(4-methoxyphenyl)urea
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4

文献信息

• Design, synthesis, and biological evaluation of phenylurea indole derivatives as ABCG2 inhibitors
  作者：Gao-Jie Ye、Chao-Yun Cai、Xing-Duo Dong、Zhuo-Xun Wu、Qiu-Xu Teng、Jing-Quan Wang、Zhe-Sheng Chen、Bo Wang

  DOI：10.1016/j.bioorg.2023.106481

  日期：2023.6

  Three series of phenylurea indole derivatives were synthesized with potent inhibitory activities on ABCG2 with simple and efficient synthetic routes. Among these compounds, four phenylurea indole derivatives 3c-3f with extended π system were discovered as the most potent ABCG2 inhibitors, while these compounds showed no inhibition on ABCB1. Compounds 3c and 3f were selected for further investigation

  通过简单高效的合成路线合成了三个系列的苯脲吲哚衍生物，它们对 ABCG2 具有强效抑制活性。在这些化合物中，发现具有扩展 π 系统的四种苯脲吲哚衍生物3c-3f是最有效的 ABCG2 抑制剂，而这些化合物对 ABCB1 没有抑制作用。选择化合物3c和3f进行进一步研究，以探索逆转 ABCG2 介导的多药耐药性 (MDR) 的作用机制。结果表明，化合物3c和3f增加了米托蒽醌 (MX) 在 ABCG2 过表达细胞中的积累，但它们没有改变 ABCG2 在细胞中的表达水平或定位。此外，两者3c和3f显着刺激 ABCG2 转运蛋白的 ATP 水解，表明它们可以成为 ABCG2 转运蛋白的竞争性底物，从而增加米托蒽醌在 ABCG2 过表达 H460/MX20 细胞中的积累。3c和3f都以高亲和力对接到人类 ABCG2 转运蛋白 (PDB 6FFC) 的药物结合位点。本研究表明，延长苯脲吲哚衍生物的π
• Synergistic effect of tryptamine-urea derivatives to overcome the chromosomally-mediated colistin resistance in Klebsiella pneumoniae
  作者：Chaimae Majdi、Jean Dessolin、David Bénimélis、Catherine Dunyach-Rémy、Alix Pantel、Patrick Meffre、Zohra Benfodda

  DOI：10.1016/j.bmc.2024.117604

  日期：2024.2