1-(4-bromobutyl)-1H-indole-3-carbaldehyde

• 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: 1-(4-bromobutyl)-1H-indole-3-carbaldehyde
• 英文别名: 1-(4-Bromobutyl)indole-3-carboxaldehyde；1-(4-bromobutyl)indole-3-carbaldehyde
• 化学式: C₁₃H₁₄BrNO
• 分子量: 280.164
• InChiKey: FVFQNGBRZGNHNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-bromobutyl)-1H-indole-3-carbaldehyde 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Rationally designed hybrid molecules with appreciable COX-2 inhibitory and anti-nociceptive activities

  摘要：

  Six molecules were obtained by the combination of three biologically and medicinally significant moieties- indole, chrysin and pyrazole. Bio-evaluation of these hybrid molecules showed significant inhibition of COX-2 enzymatic activity over that of COX-1 and appreciable anti-nociceptive activity, checked at swiss albino mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.080
• 作为产物：
  描述：

  1,4-二溴丁烷 、 3-吲哚甲醛 在 potassium phosphate 作用下， 反应 0.5h， 生成 1-(4-bromobutyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  在离子液体中一锅合成丁基-1H-吲哚-3-烷基羧酸衍生物，作为有效的双效剂，可用于管理BPH。

  摘要：

  基于两种α的SAR 1 -AR拮抗剂和5α还原酶（5AR）抑制剂，双重作用的药剂4-（1-（4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基针对BPH设计了）-1 H-吲哚-3-基）丁酸4aaa，并通过N-烷基化的两个步骤合成。新开发了针对4aaa的一锅协议。用IL [C 6分钟]溴作为溶剂，收率4AAA从16.0％提高到75.1％，反应时间是1.5小时缩短为48小时。制备了25种基于芳基哌嗪和吲哚基丁酸的具有烷基连接基的衍生物。进一步扩展了该协议，以获取另外14个衍生词，其中O-烷基化参与其中，并应用于生物有效分子DPQ和阿立哌唑的合成。预期地，化合物4AAA表现出α的双重抑制1 -AR和5α还原酶，和exihited针对人类细胞没有明显的细胞毒性。还确定了4aaa的药代动力学特性。

  DOI：

  10.1016/j.ejmech.2020.112616

文献信息

• Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C−H Bonds with Unactivated Alkyl Bromides
  作者：Wen-Jun Zhou、Guang-Mei Cao、Guo Shen、Xing-Yong Zhu、Yong-Yuan Gui、Jian-Heng Ye、Liang Sun、Li-Li Liao、Jing Li、Da-Gang Yu

  DOI：10.1002/anie.201704513

  日期：2017.12.4

  Reported herein is a novel visible‐light photoredox system with Pd(PPh3)4 as the sole catalyst for the realization of the first direct cross‐coupling of C(sp3)−H bonds in N‐aryl tetrahydroisoquinolines with unactivated alkyl bromides. Moreover, intra‐ and intermolecular alkylations of heteroarenes were also developed under mild reaction conditions. A variety of tertiary, secondary, and primary alkyl

  本文报道了一种新型的可见光光氧化还原体系，其中Pd（PPh 3）4是实现N-芳基四氢异喹啉中C（sp 3）-H键与未活化烷基溴的第一个直接交叉偶联的唯一催化剂。此外，杂芳烃的分子内和分子间烷基化反应也在温和的反应条件下进行。各种叔，仲和伯烷基溴经过反应生成C（sp 3）-C（sp 3）和C（sp 2）-C（sp 3）债券，收益率中等至极高。这些氧化还原中性反应具有广泛的底物范围（> 60个示例），良好的功能基团耐受性和易于生成的四元中心。机理研究表明，简单的钯配合物充当可见光光催化剂，自由基参与该过程。
• The one-pot synthesis of butyl-1H-indol-3-alkylcarboxylic acid derivatives in ionic liquid as potent dual-acting agent for management of BPH
  作者：Li-Yan Zeng、Fubiao Yang、Kaixuan Chen、Yunong Zeng、Zhenzhou Jiang、Shuwen Liu、Baomin Xi

  DOI：10.1016/j.ejmech.2020.112616

  日期：2020.11

  H-indol-3-yl)butanoic acid 4aaa was designed against BPH and synthesized by two steps of N-alkylation. One-pot protocol towards 4aaa was newly developed. With IL [C6min]Br as solvent, the yield of 4aaa was increased to 75.1 % from 16.0 % and the reaction time was shortened in 1.5 hours from 48 hours. 25 Derivatives structurally based on arylpiperazine and indolyl butyric acid with alkyl linker were

  基于两种α的SAR 1 -AR拮抗剂和5α还原酶（5AR）抑制剂，双重作用的药剂4-（1-（4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基针对BPH设计了）-1 H-吲哚-3-基）丁酸4aaa，并通过N-烷基化的两个步骤合成。新开发了针对4aaa的一锅协议。用IL [C 6分钟]溴作为溶剂，收率4AAA从16.0％提高到75.1％，反应时间是1.5小时缩短为48小时。制备了25种基于芳基哌嗪和吲哚基丁酸的具有烷基连接基的衍生物。进一步扩展了该协议，以获取另外14个衍生词，其中O-烷基化参与其中，并应用于生物有效分子DPQ和阿立哌唑的合成。预期地，化合物4AAA表现出α的双重抑制1 -AR和5α还原酶，和exihited针对人类细胞没有明显的细胞毒性。还确定了4aaa的药代动力学特性。
• Indole Functionalization via Photoredox Gold Catalysis
  作者：Sherif J. Kaldas、Alexandre Cannillo、Terry McCallum、Louis Barriault

  DOI：10.1021/acs.orglett.5b01260

  日期：2015.6.5

  photoredox catalyst [Au2(dppm)2]Cl2 to initiate free-radical cyclizations onto indoles is reported. Excitation of the dimeric Au(I) photocatalyst for the reduction of unactivated bromoalkanes and bromoarenes is used for the generation of carbon-centered radicals. Previous to this work, reduction processes leading to indole functionalization utilizing photoredox catalysts were limited to activated benzylic

  报道了使用光氧化还原催化剂[Au 2（dppm）2 ] Cl 2来引发在吲哚上的自由基环化。激发二聚体Au（I）光催化剂以还原未活化的溴代烷烃和溴代芳烃用于碳中心自由基的产生。在这项工作之前，利用光氧化还原催化剂导致吲哚官能化的还原过程仅限于活化的苄基或α-羰基定位的溴代烷烃。该方法为有机锡烷和发火引发剂提供了温和且安全的替代方法，可用于获得以前通过催化或化学计量方法无法获得的高能自由基。
• Synthesis and photochromic properties of a novel thiol-terminated 1,3-diazabicyclo[3.1.0]hex-3-ene on silver nanoparticles
  作者：Atefeh Ghavidast、Nosrat O. Mahmoodi、Mohammad Ali Zanjanchi

  DOI：10.1016/j.molstruc.2013.05.054

  日期：2013.9

  Abstract Inorganic nanoparticles functionalized with organic photochromes have been used for a much wider variety of applications. In this work, we have designed and synthesized a novel photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene with a thiol-terminal group to form a self-assembled monolayer on the silver nanoparticles (AgNPs). The prepared photochromic material was characterized using X-ray diffraction

  摘要 用有机光致变色功能化的无机纳米粒子已被用于更广泛的应用。在这项工作中，我们设计并合成了一种新型光致变色 1,3-二氮杂双环 [3.1.0]hex-3-ene，其具有硫醇末端基团，可在银纳米粒子 (AgNPs) 上形成自组装单层。使用X射线衍射、扫描电子显微镜、UV-Vis、NMR和IR方法对制备的光致变色材料进行表征。结果分析表明，AgNPs 与光致变色的末端硫醇基团之间存在化学相互作用。分析了光致变色配体和光致变色/AgNPs 组件的光致变色结构行为关系（PSBR）。
• Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent
  作者：Palwinder Singh、Jagroop Kaur、Gurjit Singh、Rajbir Bhatti

  DOI：10.1021/acs.jmedchem.5b00952

  日期：2015.8.13

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.