3-(2-phenyl-1H-indol-3-yl)-propylamine | 137116-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(2-phenyl-1H-indol-3-yl)-propylamine
• 英文别名: 3-(3-aminopropyl)-2-phenylindole；3-(2-phenyl-1H-indol-3-yl)propan-1-amine；3-(2-phenyl-indol-3-yl)-propylamine
• CAS: 137116-97-3
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: RLYBDZCAUFEUIH-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-phenyl-1H-indol-3-yl)-propylamine 在 sodium hydroxide 、 potassium tert-butylate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 45.15h， 生成 3-[3-(3-tert-butoxycarbonylamino-propyl)-2-phenyl-indol-1-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Combinatorial synthesis of substituted 3-(2-indolyl)piperidines and 2-phenyl indoles as inhibitors of ZipA–FtsZ interaction

  摘要：

  The ZipA-FtsZ protein-protein interaction is a potential target for antibacterial therapy. The design and parallel synthesis of a combinatorial library of small molecules, which target the FtsZ binding area on ZipA are described. Compounds were demonstrated to bind to the FtsZ binding domain of ZipA by HSQC NMR and to inhibit cell division in a cell elongation assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.031
• 作为产物：
  描述：

  4-苯甲酰基丁酸 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 3-(2-phenyl-1H-indol-3-yl)-propylamine
  参考文献：
  名称：

  Combinatorial synthesis of substituted 3-(2-indolyl)piperidines and 2-phenyl indoles as inhibitors of ZipA–FtsZ interaction

  摘要：

  The ZipA-FtsZ protein-protein interaction is a potential target for antibacterial therapy. The design and parallel synthesis of a combinatorial library of small molecules, which target the FtsZ binding area on ZipA are described. Compounds were demonstrated to bind to the FtsZ binding domain of ZipA by HSQC NMR and to inhibit cell division in a cell elongation assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.031

文献信息

• Synthesis of Spiroindolenines by Iodine‐Mediated Dearomative Aza‐Spirocyclization of Indoles
  作者：Zongxiang Zhao、Huilin Qiu、Junbiao Chang、Wenquan Yu

  DOI：10.1002/adsc.202400046

  日期：2024.4.23

  A transition‐metal‐free dearomative aza‐spirocyclization reaction of 2,3‐disubstituted indoles is established by using molecular iodine under basic conditions. The required substrates were prepared via sequential Fisher indole synthesis and sulfonylation. This dearomatization reaction is amenable to gram‐scale synthesis, and provides access to various spiroindolenine derivatives from indole sulfonamide

  在碱性条件下使用分子碘建立了 2,3-二取代吲哚的无过渡金属脱芳香氮杂螺环化反应。通过连续的费舍尔吲哚合成和磺酰化制备所需的底物。这种脱芳构化反应适合克级合成，并提供从吲哚磺酰胺前体获得各种螺吲哚衍生物的途径。
• Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2139 - 2145
  作者：Benincori, Tiziana、Brenna, Elisabetta、Sannicolo, Franco

  DOI：——

  日期：——
• Combinatorial synthesis of substituted 3-(2-indolyl)piperidines and 2-phenyl indoles as inhibitors of ZipA–FtsZ interaction
  作者：Lee D. Jennings、Kenneth W. Foreman、Thomas S. Rush、Desiree H.H. Tsao、Lidia Mosyak、Scott L. Kincaid、Mohani N. Sukhdeo、Alan G. Sutherland、Weidong Ding、Cynthia Hess Kenny、Chantel L. Sabus、Hanlan Liu、Elizabeth G. Dushin、Soraya L. Moghazeh、Pornpen Labthavikul、Peter J. Petersen、Margareta Tuckman、Alexey V. Ruzin

  DOI：10.1016/j.bmc.2004.07.031

  日期：2004.10

  The ZipA-FtsZ protein-protein interaction is a potential target for antibacterial therapy. The design and parallel synthesis of a combinatorial library of small molecules, which target the FtsZ binding area on ZipA are described. Compounds were demonstrated to bind to the FtsZ binding domain of ZipA by HSQC NMR and to inhibit cell division in a cell elongation assay. (C) 2004 Elsevier Ltd. All rights reserved.