1-(5-bromopentyl)indole-3-carbaldehyde | 1190367-91-9

• 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-(5-bromopentyl)indole-3-carbaldehyde
• CAS: 1190367-91-9
• 化学式: C₁₄H₁₆BrNO
• 分子量: 294.191
• InChiKey: VRMRJYPYYHJUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-(5-bromopentyl)indole-3-carbaldehyde 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 5-{1-[5-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)pentyl]-1H-indol-3-ylmethylene}-1,3-dimethylpyrimidine-2,4,6-trione
  参考文献：
  名称：

  Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.5b00952
• 作为产物：
  描述：

  吲哚 在 三聚氯氰 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 1-(5-bromopentyl)indole-3-carbaldehyde
  参考文献：
  名称：

  使用2,4,6-三氯-1,3,5-三嗪/二甲基甲酰胺（TCT / DMF）混合试剂对吲哚（C3）和吡咯（C2）进行选择性和高效甲酰化

  摘要：

  这项研究介绍了一种有效的方法，分别在C（3）和C（2）的位置对吲哚和吡咯进行选择性甲酰化。三当量的N，N-二甲基甲酰胺和一当量的2,4,6-三氯-1,3,5-三嗪（氰尿酰氯）的混合物可生成易于处理的甲酰化剂，以有效地将此类化合物甲酰化为在温和的反应条件下得到相应的醛。该方法是高效的，并且以良好至优异的产率获得了一系列甲酰化的吲哚和吡咯。

  DOI：

  10.1002/jhet.2652

文献信息

• Design, Synthesis, and Antimicrobial Activity Evaluation of Ciprofloxacin—Indole Hybrids
  作者：Mingxia Song、Yi Hua、Yuxin Liu、Xunli Xiao、Haihong Yu、Xianqing Deng

  DOI：10.3390/molecules28176325

  日期：——

  spectrometry. The in vitro antibacterial activities of these hybrids against gram-positive and gram-negative pathogens, including four multidrug-resistant clinical isolates, were evaluated and compared with those of the parent drug ciprofloxacin (CIP). All the target compounds (MIC = 0.0625–32 μg/mL) exhibited excellent inhibitory activity against the strains tested. Among them, 3a (MIC = 0.25–8 μg/mL) showed

  随着抗菌药物的过度使用和滥用，抗菌药物耐药性正在成为一个严重的全球健康问题。新型抗菌药物是克服耐药危机的有效措施。在本文中，借助核磁共振和高分辨率质谱，设计、合成了一组新型环丙沙星-吲哚/苯乙酮杂化物，并对其结构进行了阐明。评估了这些杂种对革兰氏阳性和革兰氏阴性病原体（包括四种多重耐药临床分离株）的体外抗菌活性，并与母体药物环丙沙星（CIP）进行了比较。所有目标化合物（MIC = 0.0625–32 μg/mL）对测试菌株均表现出优异的抑制活性。其中，3a（MIC = 0.25–8 μg/mL）显示出与 CIP 相当或稍弱的活性。最活跃的杂交体 8b (MIC = 0.0626–1 μg/mL) 显示出与 CIP 相同或更高的活性。此外，化合物 8b 显示出优于 CIP 的杀菌能力，且耐药频率低得难以检测。此外，进行的分子对接研究表明，8b 和 CIP 与 DNA 旋转酶（金黄色葡萄球菌）具有相似的结合模式。因此，混合体
• Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine−Aplysinopsin Hybrid Molecule
  作者：Sharad Porwal、Shikha S. Chauhan、Prem M. S. Chauhan、Nishi Shakya、Aditya Verma、Suman Gupta

  DOI：10.1021/jm900564x

  日期：2009.10.8

  In an attempt to synthesize pent amidine - aplysinopsin hybrid molecule 25, a lead molecule 8 (containing Z-configured aplysinopsin moiety) was identified for antileishmanial activity. Optimization of lead 8 provided 24 (containing E-configured aplysinopsin) possessing 10 times more activity and 401-fold less toxicity than the drug pentamidine in cell based assays. Synthesis of 24 was possible, surprisingly, because of two innate reactivities of indole-3-carbaldehyde which provided it in diastereoand regio-selectively pure form without recourse to the long reaction pathway.
• gem -Dithioacetylated indole derivatives as novel antileishmanial agents
  作者：Sharad Porwal、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2017.09.018

  日期：2017.10

  In this communication we report a serendipitously discovered hybrid molecule 1, combining fragment of 3 (an in vivo active antileishmanial molecule) with H2S donor moiety (known for bimodal behavior of cytoprotection and apoptosis), as antileishmanial agent. Compound 1 suppresses 99.82% parasitemia of L donovani infected macrophages at 12.5 mu g/ml without even deforming them (CC50 > 100 mu g/ml). This compound appears cytotoxic for intracellular amastigotes while cytoprotective to host macrophages. The concept can be utilized to develop high therapeutic index NCE (New Chemical Entities) for other macrophage mediated diseases like tuberculosis and cancer. (c) 2017 Elsevier Ltd. All rights reserved.