1,1'-(propane-1,3-diyl)bis(1H-indole-3-carbaldehyde) | 936939-87-6

• 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: 1,1'-(propane-1,3-diyl)bis(1H-indole-3-carbaldehyde)
• 英文别名: 1,1a(2)-(1,3-Propanediyl)bis[1H-indole-3-carboxaldehyde]；1-[3-(3-formylindol-1-yl)propyl]indole-3-carbaldehyde
• CAS: 936939-87-6
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: SUSMGSKTKVKTKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1'-(propane-1,3-diyl)bis(1H-indole-3-carbaldehyde) 在 copper diacetate 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以63%的产率得到10,14-Diazapentacyclo[12.7.0.02,10.04,9.015,20]henicosa-1(21),2,4,6,8,15,17,19-octaene-3,21-dicarbaldehyde
  参考文献：
  名称：

  Rh（iii）催化的串联吲哚C4芳基化/蒽环化：吲哚喹啉的获取及其在光物理研究中的应用。

  摘要：

  开发了一种有效的Rh（iii）催化的直接策略，用于吲哚衍生物与蒽的串联C4芳基化/环化反应，以提供吲哚喹啉部分。该方法简单易行，具有区域选择性和功能基团耐受性。机理研究表明，新安装的氮杂环在O保护的醛肟向其氰基衍生物的转化中起着重要作用。进行了研究以探索获得的吲哚喹啉衍生物的有希望的光物理性质。

  DOI：

  10.1039/c9cc08372c
• 作为产物：
  描述：

  3-吲哚甲醛 、 1,3-二溴丙烷 在 potassium carbonate 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 16.0h， 以81%的产率得到1,1'-(propane-1,3-diyl)bis(1H-indole-3-carbaldehyde)
  参考文献：
  名称：

  用于中环合成的分子内氧化 C−H 偶联

  摘要：

  描述了用于中环合成的氧化 CH 偶联。

  DOI：

  10.1021/ja1090854

文献信息

• TNF-α and IL-6 inhibitors: Conjugates of N-substituted indole and aminophenylmorpholin-3-one as anti-inflammatory agents
  作者：Palwinder Singh、Sukhmeet Kaur、Anuradha Sharma、Gurcharan Kaur、Rajbir Bhatti

  DOI：10.1016/j.ejmech.2017.09.003

  日期：2017.11

  The conjugates obtained by the combination of indole and aminophenyl morpholinone were screened for TNF-α and IL-6 inhibition in microglial cells. Compound 4 was found to be the most potent anti-inflammatory agent as it reduced LPS induced level of inflammatory cytokines TNF-α and IL-6 by 71% and 53%, respectively. A significant decrease in NO and MMPs release from BV2 cells in culture pretreated with

  筛选由吲哚和氨基苯基吗啉酮组合获得的缀合物在小胶质细胞中的TNF-α和IL-6抑制作用。发现化合物4是最有效的抗炎剂，因为其将LPS诱导的炎性细胞因子TNF-α和IL-6的水平分别降低了71％和53％。在用该化合物预处理的培养物中，从BV2细胞释放的NO和MMP明显减少，并且抑制了NF-κB和AP-1的核转运。在化合物4的存在下，观察到瑞士白化病小鼠中乙酸诱导的痛觉过敏的抑制率为75％。实验数据和分子对接研究表明这些化合物靶向TNF-α，iNOS和IL-6。
• 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.
• Biologically active Schiff bases as potentiometric sensor for the selective determination of Nd3+ ion
  作者：Koteswara Rao Bandi、Ashok Kumar Singh、Anjali Upadhyay

  DOI：10.1016/j.electacta.2013.05.038

  日期：2013.8

  Novel multidentate Schiff bases 5-((1-(3-(3-((5-mercapto-1,3,4-thiadiazol-2-ylimino)methyl)-1H-indol-1-yl)propyl)-1H-indol-3-yl)methyleneamino)-1,3,4-thiadiazole-2-thiol) (S-1) and N-((1-(3-(3-((thiazol-2-ylimino)methyl)-1H-indol-1-yl)propyl)-1H-indol-3-yl)methylene)thiazol-2-amine (S-2) were synthesized for the construction of Nd3+ ion-selective electrode. The polymeric membrane electrodes (PME) were fabricated along with various plasticizers and additive. It is found that the PME based on S-1 having the composition (S-1 : (potassium tetrakis p-(chloro phenyl)borate) KTpCIPB: (o-nitrophenyloctyl ether) o-NPOE: PVC 4:2:58:36, w/w, mg) is found to be better. Thus, the coated graphite electrode (CGE) was constructed with the same composition and the results were compared with PME. The CGE is found to be better in comparison to PME with respect to all the potentiometric characteristics such as low detection limit (1.1 x 10(-8) mol L-1), wide working concentration range (3.1 x 10(-8)-1.0 x 10(-1) mol L-1), near Nernstian slope (19.8 +/- 0.3 mV decade(-1) of activity.), low response time (10 s), shelf life time (105 days) and wide pH range (3.5-8.0). Both the PME and CGE were used for the quantifying the Nd3+ ion in various samples such as water, soil samples, binary mixtures and as an indicator electrode using EDTA. PME and CGE were also used for the determination of F- ion in mouth wash solution and tooth paste sample. Further the antibacterial activity of Schiff bases were examined by broth micro-dilution method and found that these are antibiotics against Staphylococcus aureus (Gram positive) and Escherichia coli (ATCC25922) (Gram negative). (c) 2013 Elsevier Ltd. All rights reserved.