1,5-Bis-(3-formylindol-1-yl)-pentan | 95432-96-5

• 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-Bis-(3-formylindol-1-yl)-pentan
• 英文别名: 1,1'-pentane-1,5-diyl-bis-indole-3-carbaldehyde；1-[5-(3-Formylindol-1-yl)pentyl]indole-3-carbaldehyde
• CAS: 95432-96-5
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: VAAJFERPENUVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-Bis-(3-formylindol-1-yl)-pentan 、 氨基硫脲 、 alpha-溴-4-甲氧基苯乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以82%的产率得到
  参考文献：
  名称：

  一锅多组分合成吲哚-3-基肼基噻唑作为抗菌剂

  摘要：

  通过单或双（吲哚-3-甲醛），硫代氨基脲和苯甲酰基溴的一锅环缩合，有效地合成了一系列新颖的单和双（吲哚-3-基）肼基噻唑衍生物。产物的结构通过傅里叶变换红外（FT-IR），1 H核磁共振（NMR）和13 C NMR光谱确认。评价所有合成的化合物对革兰氏阳性菌（枯草芽孢杆菌和琵琶微球菌）和革兰氏阴性菌（铜绿假单胞菌和沙门氏菌肠炎）的体外抗菌活性。）。在筛选出的化合物中，发现有少数是高效的抗菌剂。具有OCH 3给予基团的双化合物对革兰氏阳性细菌表现出良好的活性。

  DOI：

  10.1007/s11164-016-2478-y
• 作为产物：
  描述：

  3-吲哚甲醛 、 1,5-二溴戊烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68%的产率得到1-(5-bromopentyl)indole-3-carbaldehyde
  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

文献信息

• One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole Derivatives Using Zn²⁺@KSF and Their Antibacterial Activity
  作者：Nosrat O. Mahmoodi、Iraj Nikokar、Marzieh Farhadi、Atefeh Ghavidast

  DOI：10.5560/znb.2014-4026

  日期：2014.6.1

  bis-indolylimidazole derivatives using Zn2+ supported on montmorillonite KSF (Zn2+@KSF) as an efficient heterogeneous catalyst is described. The structures of these compounds were characterized by IR, 1H NMR and 13C NMR spectroscopy. The antibacterial activity of the selected products was examined. Some products exhibit promising activities. Graphical Abstract One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole

  描述了使用负载在蒙脱石 KSF (Zn2+@KSF) 上的 Zn2+ 作为有效的多相催化剂制备单和双吲哚基咪唑衍生物。这些化合物的结构通过IR、1H NMR和13C NMR光谱表征。检查所选产品的抗菌活性。一些产品表现出有希望的活性。图解摘要 使用 Zn2+@KSF 的单和双吲哚咪唑衍生物的一锅多组分合成及其抗菌活性
• One-pot multicomponent synthesis of indol-3-yl-hydrazinyl thiazoles as antimicrobial agents
  作者：Nosrat O. Mahmoodi、Behzad Khalili、Olia Rezaeianzade、Atefeh Ghavidast

  DOI：10.1007/s11164-016-2478-y

  日期：2016.8

  were efficiently synthesized via one-pot cyclocondensation of mono- or bis(indole-3-carbaldehyde), thiosemicarbazide, and phenacyl bromides. The structure of the products was confirmed by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. All synthesized compounds were evaluated for in vitro antibacterial activity against Gram-positive (Bacillus subtilis and

  通过单或双（吲哚-3-甲醛），硫代氨基脲和苯甲酰基溴的一锅环缩合，有效地合成了一系列新颖的单和双（吲哚-3-基）肼基噻唑衍生物。产物的结构通过傅里叶变换红外（FT-IR），1 H核磁共振（NMR）和13 C NMR光谱确认。评价所有合成的化合物对革兰氏阳性菌（枯草芽孢杆菌和琵琶微球菌）和革兰氏阴性菌（铜绿假单胞菌和沙门氏菌肠炎）的体外抗菌活性。）。在筛选出的化合物中，发现有少数是高效的抗菌剂。具有OCH 3给予基团的双化合物对革兰氏阳性细菌表现出良好的活性。
• 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.