2-(5-fluoro-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride | 1048343-51-6

• 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: 2-(5-fluoro-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride
• 英文别名: 2-(5-fluoro-2-methyl-1H-indol-3-yl)ethanamine hydrochloride；2-(5-Fluoro-2-methyl-1H-indol-3-yl)-ethylamine hydrochloride；2-(5-fluoro-2-methyl-1H-indol-3-yl)ethanamine;hydrochloride
• CAS: 1048343-51-6
• 化学式: C₁₁H₁₃FN₂*ClH
• 分子量: 228.697
• InChiKey: UJHALVSHVYZJDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-fluoro-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 生成 tert-butyl (2-(1-benzyl-5-fluoro-2-methyl-1H-indol-3-yl)ethyl)carbamate
  参考文献：
  名称：

  Branching tryptamines as a tool to tune their antiproliferative activity

  摘要：

  The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.028
• 作为产物：
  描述：

  环丙甲基酮 、 4-氟苯肼盐酸盐 以 乙腈 为溶剂， 反应 25.0h， 生成 2-(5-fluoro-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride
  参考文献：
  名称：

  Branching tryptamines as a tool to tune their antiproliferative activity

  摘要：

  The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.028

文献信息

• [EN] FUSED BICYCLIC ALKYLENE LINKED IMIDODICARBONIMIDIC DIAMIDES, METHODS FOR SYNTHESIS, AND USES IN THERARY<br/>[FR] DIAMIDES IMIDODICARBONIMIDIQUES LIÉS À UN ALKYLÈNE BICYCLIQUE FUSIONNÉ, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS DANS UNE THÉRAPIE
  申请人：NOVATARG INC

  公开号：WO2018106907A1

  公开（公告）日：2018-06-14

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3- yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3- yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5' adenosine monophosphate-activated protein kinase (AMPK).

  本发明提供了新型的融合的双环烷基亚乙基连接的咪唑二氨基碳亚胺二酰胺。具体来说，本文描述了N-[2-(吲哚-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺和N-[2-(吡咯吡啶-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺（化合物的结构式（I）或结构式（II）），以及其用途。本发明的化合物被认为是有机阳离子转运体选择性化合物，可用于治疗由于5'腺苷单磷酸活化蛋白激酶（AMPK）活性降低而引起的疾病和症状。
• Synthesis, Screening and Characterization of Novel Potent Arp2/3 Inhibitory Compounds Analogous to CK-666
  作者：Artem I. Fokin、Roman N. Chuprov-Netochin、Alexander S. Malyshev、Stéphane Romero、Marina N. Semenova、Leonid D. Konyushkin、Sergey V. Leonov、Victor V. Semenov、Alexis M. Gautreau

  DOI：10.3389/fphar.2022.896994

  日期：——

  migration, where they drive membrane protrusions of lamellipodia. Several Arp2/3 inhibitory compounds have been identified. Among them, the most widely used is CK-666 (2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-benzamide), whose mode of action is to prevent Arp2/3 from reaching its active conformation. Here 74 compounds structurally related to CK-666 were screened using a variety of assays. The primary screen

  由肌动蛋白相关蛋白 2 和 3 (Arp2/3) 复合物聚合的分支肌动蛋白网络在力产生和膜重塑中起关键作用。这些网络对于细胞迁移特别重要，它们驱动片状伪足的膜突起。已鉴定出几种 Arp2/3 抑制化合物。其中应用最广的是CK-666 (2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-benzamide)，其作用方式是防止Arp2/3从达到其活性构象。在这里，使用各种检测方法筛选了 74 种与 CK-666 结构相关的化合物。主要筛选涉及在未转化的 MCF10A 细胞中掺入 EdU（5-乙炔基-2'-脱氧尿苷）。由此产生的九个阳性命中都在二次筛选中阻断了 B16-F1 黑色素瘤细胞中的片状突起和细胞迁移，表明细胞周期进程可以是 Arp2/3 活性的有用读数。选定的化合物也在海胆胚胎中进行了表征，其中 Arp2/3 抑制产生特定的表型，例如缺乏三辐射骨
• Fused bicyclic alkylene linked imidodicarbonimidic diamides, methods for synthesis, and uses in therapy
  申请人：NovaTarg, Inc.

  公开号：US11261157B2

  公开（公告）日：2022-03-01

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3-yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3-yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5′ adenosine monophosphate-activated protein kinase (AMPK).

  本发明提供了新颖的融合双环烯基连接的咪唑二碳酰亚胺二酰胺。特别是，本发明描述了 N-[2-(吲哚-3-基)亚烷基]连接的咪唑二碳酰亚胺二酰胺和 N-[2-(吡咯并吡啶-3-基)亚烷基]连接的咪唑二碳酰亚胺二酰胺（式 (I) 或式 (II) 的化合物）及其用途。本发明的化合物被认为是有机阳离子转运体选择性化合物，可用于治疗由 5′单磷酸腺苷激活蛋白激酶（AMPK）活性降低引起的疾病和病症。
• FUSED BICYCLIC ALKYLENE LINKED IMIDODICARBONIMIDIC DIAMIDES, METHODS FOR SYNTHESIS, AND USES IN THERAPY
  申请人：NovaTarg, Inc.

  公开号：US20190345103A1

  公开（公告）日：2019-11-14

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3-yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3-yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5′ adenosine monophosphate-activated protein kinase (AMPK).
• Branching tryptamines as a tool to tune their antiproliferative activity
  作者：Rinat F. Salikov、Konstantin P. Trainov、Irina K. Belousova、Aleksandr Yu. Belyy、Ulyana Sh. Fatkullina、Regina V. Mulyukova、Liana F. Zainullina、Yulia V. Vakhitova、Yury V. Tomilov

  DOI：10.1016/j.ejmech.2017.12.028

  日期：2018.1

  The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity. (C) 2017 Elsevier Masson SAS. All rights reserved.