N-(3-bromopropyl)-1H-indole-2-carboxamide

• 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: N-(3-bromopropyl)-1H-indole-2-carboxamide
• 英文别名: N2-(3-bromopropyl)-1H-2-indolecarboxamide；N-2-(3-bromopropyl)-1H-2-indole-carboxamide
• 化学式: C₁₂H₁₃BrN₂O
• 分子量: 281.152
• InChiKey: CBGRXJXWXTXFBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-1H-indole-2-carboxamide 、 4-苄基哌啶 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以45%的产率得到N-(3-(4-benzylpiperidin-1-yl)propyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors

  摘要：

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.022
• 作为产物：
  描述：

  吲哚-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3-bromopropyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors

  摘要：

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.022

文献信息

• Novel pyrrolo[2,1-c][1,4] benzodiazepine-indole derivatives, their preparation process, and uses of the same
  申请人：Kaohsiung Medical University

  公开号：US20040054168A1

  公开（公告）日：2004-03-18

  Disclosed herein are novel pyrrolo[2,1-c][1,4]benzodiazepine-indole derivatives of formula (I): 1 wherein each of the substituents is given the definition as set forth in the Specification and claims. Also disclosed are the preparation process of these derivatives and their uses in the manufacture of pharmaceutical compositions.

  本文披露了一种新颖的嘧啶并[2,1-c][1,4]苯二氮杂环己烯-吲哚衍生物，化学式（I）如下：其中每个取代基的定义如规范和索赔中所述。还披露了这些衍生物的制备过程以及它们在制造药物组合物中的用途。
• Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids
  作者：Ling Huang、Tao Su、Wenjun Shan、Zonghua Luo、Yang Sun、Feng He、Xingshu Li

  DOI：10.1016/j.bmc.2012.02.059

  日期：2012.5

  A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017 mu M. This compound demonstrated similar A beta aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 mu M, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Biological Evaluation of Pyrrolo[2,1-<i>c</i>][1,4]benzodiazepine and Indole Conjugates as Anticancer Agents
  作者：Jeh-Jeng Wang、Yu-Kai Shen、Wan-Ping Hu、Ming-Chu Hsieh、Fu-Lung Lin、Ming-Kuan Hsu、Mei-Hui Hsu

  DOI：10.1021/jm050956q

  日期：2006.2.1

  A series of novel pyrrolo[2,1-c][1,4]benzodiazepine (PBD) hybrids linked with indole carboxylates is described. These compounds were prepared by linking C-8 of 3 (DC-81) with an indole 2-carbonyl moiety (9) through carbon chain linkers to afford PBD hybrid agents 17-21 in good yields. Preliminary in vivo tests show that these hybrid agents have potent antitumor activity. The cytotoxic studies of the hybrid agents on human melanoma A2058 cells indicate most of the hybrids induced higher cytotoxicity, better DNA-binding ability, an increase in the apoptotic sub-G1 population, and a significant reduction in Delta Psi(mt) relative to compound 3. In addition, DNA flow cytometric analysis shows that hybrids actively induce a marked loss of cells from the G2/M phase of the cell cycle, which progresses to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI). Thus, we suggest that the hybrid agents are potent inducers of cell apoptosis in A2058 cells.
• US6939869B2
  申请人：——

  公开号：US6939869B2

  公开（公告）日：2005-09-06
• Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors
  作者：Suresh Paudel、Yongkai Cao、Shuohan Guo、Byeongkwan An、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2015.08.022

  日期：2015.10

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.