5030-96-6

Upstream product

• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 10075-50-0 5-bromo-1H-indole 
• 100-97-0 hexamethylenetetramine 
• 92557-51-2 5-Bromo-indole-3-carbinol 
• 67-56-1 methanol 
• 127-19-5 N,N-dimethyl acetamide 
• 50-00-0 formaldehyd 
• 40432-84-6 (5-bromo-1H-indol-3-yl)-acetic acid 

Relevant academic research and scientific papers

Synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives via reductive heteroarylation

An efficient and general reductive heteroarylation approach toward the synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives has been developed. Thus, treatment of acylpyrrole or acylindole derivatives with indoles or pyrroles in the presence of a combination of sodium borohydride and acetic acid resulted in the formation of the title compounds in moderate to excellent isolated yields.

Application of alkaloid arundine and derivatives thereof in prevention and control of plant viruses and pathogenic bacteria

The invention relates to an application of alkaloid arundine and derivatives thereof in control of plant virus pathogens. It is found that arundine and derivatives I-1 to I-25 thereof show good anti-plant virus pathogen activity for the first time, and can well inhibit 14 plant germs including tobacco mosaic virus (TMV), cucumber fusarium wilt, peanut brown spot, apple ring spot, wheat sheath blight, corn bipolaris maydis, watermelon anthracnose, fusarium moniliforme, tomato early blight, wheat gibberellic disease, rice blast, phytophthora capsici, sclerotium of rape, cucumber gray mold and rice sheath blight.

Natural products for biocides discovery: Discovery of arundine and it's derivatives as novel antiviral and anti-phytopathogenic-fungus agents

Plant diseases are one of the natural disasters that seriously harm agricultural production, and it is very difficult to control. The discovery of new antiviral and antifungal lead compounds becomes more and more important. Natural product arundine was found to have anti-tobacco mosaic virus (TMV) activity and anti-phytopathogenic-fungus activity for the first time. A series of arundine analogues were designed, synthesized and evaluated for their antiviral and fungicidal activities. Compound 6 with excellent antiviral activity emerged as novel antiviral lead compound. Compound 7 with 12.6?38.3 μg/mL EC50 values against 14 plant pathogens emerged as novel antifungal lead compound. This work laid a foundation for promoting the application of arundine analogues in plant protection.

CuI-catalyzed highly regioselective C[sbnd]H functionalization of indoles using indole-3-tosylhydrazones as carbene precursor: An efficient synthesis of 3,3-bis(indolyl)methane derivatives

Herein, we have developed a novel approach for synthesizing symmetrical and unsymmetrical 3,3-bis(indolyl)methane derivatives via CuI-catalyzed C[sbnd]H functionalization of indole using indole-3-tosylhydrazones as carbene precursor. This procedure works well with different substitutions such as NO2, Br, CH3 and OMe on indole or indole-3-tosylhydrazones and features high regioselectivity for C-3 functionalization over the C-1 and N-1 positions. Further, we have also revealed the feasibility of this protocol in a one-pot fashion starting from indole-3-carboxyaldehyde.

Synthesis of Unnatural Arundines Using a Magnetically Reusable Copper Ferrite Catalyst

We report a method for copper ferrite-catalyzed coupling of indoles and N, N -dimethylacetamide (DMA) to afford Arundine derivatives. Halogen, methoxy, boronate ester, and trimethylsilyl functionalities are compatible with reaction conditions. Unprotected or sterically hindered indoles are also competent substrates. Indoles containing competitively reactive pyrazoles deliver the desired products in reasonable yields. The copper ferrite is easily recovered and reused, up to nine times without a significant yield loss.

Diindolylmethane Derivatives: Potent Agonists of the Immunostimulatory Orphan G Protein-Coupled Receptor GPR84

The Gi protein-coupled receptor GPR84, which is activated by (hydroxy)fatty acids, is highly expressed on immune cells. Recently, 3,3′-diindolylmethane was identified as a heterocyclic, nonlipid-like GPR84 agonist. We synthesized a broad range of diindolylmethane derivatives by condensation of indoles with formaldehyde in water under microwave irradiation. The products were evaluated at the human GPR84 in cAMP and β-arrestin assays. Structure-activity relationships (SARs) were steep. 3,3′-Diindolylmethanes bearing small lipophilic residues at the 5- and/or 7-position of the indole rings displayed the highest activity in cAMP assays, the most potent agonists being di(5-fluoro-1H-indole-3-yl)methane (38, PSB-15160, EC50 80.0 nM) and di(5,7-difluoro-1H-indole-3-yl)methane (57, PSB-16671, EC50 41.3 nM). In β-arrestin assays, SARs were different, indicating biased agonism. The new compounds were selective versus related fatty acid receptors and the arylhydrocarbon receptor. Selected compounds were further investigated and found to display an ago-allosteric mechanism of action and increased stability in comparison to the lead structure.

Curtius-like Rearrangement of an Iron-Nitrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes

A Curtius-like rearrangement of hydroxamates to isocyanates was discovered. This reaction was initiated from an iron(II)-nitrenoid complex, which was generated by the iron(II)-catalyzed cleavage of N-O bonds of functionalized hydroxamates. To demonstrate the efficiency of this new Curtius-like rearrangement in synthetic chemistry, a biomimetic strategy for the one-pot preparation of bisindolylmethanes was developed.

Graphene oxide decorated with Cu(i)Br nanoparticles: A reusable catalyst for the synthesis of potent bis(indolyl)methane based anti HIV drugs

A GO-Cu(i)Br nanocatalyst has been prepared, and applied for the synthesis of bis(indolyl)methanes. The catalyst is highly effective, is required in much lower amounts (0.05 mol%), and is recyclable for up to six reaction cycles without loss in activity. The synthesized compounds have been screened for their in vitro anti-HIV-1 activity, and compound 3d has shown significant anti-HIV-1 effects. Molecular modelling of 3d with reverse transcriptase enzyme has been carried out to understand its binding mechanism to the active enzyme site.

Direct use of methanol as an alternative to formaldehyde for the synthesis of 3, 3′-bisindolylmethanes (3, 3′-BIMs)

The article examines the direct use of methanol as an alternative to formaldehyde for the synthesis of 3,3'-Bisindolylmethanes (3,3'-BIM). The use of abundant and renewable feedstock reagents to construct C-C bonds, the essential link in all organic molecules, represents one of the most central subjects. Methanol, the simplest alcohol, can be made from fossil fuels, such as natural gas and coal, renewable resources, such as biomass and landfill gas, and carbon dioxide from the atmosphere. The catalytic dehydrogenation of methanol was regarded as the crucial step for such transformation. Very recently, Beller and co-workers demonstrated ruthenium-catalyzed dehydrogenation of methanol to hydrogen and C1 residuals.

Eco-friendly synthesis and study of new plant growth promoters: 3,3′-Diindolylmethane and its derivatives

3,3′-Diindolylmethane (DIM) derivatives 3a-k, prepared in one-pot from indoles 1a-k and hexamethylenetetramine (2) using ionic liquid [Bmim]BF4 as eco-friendly recyclable solvent as well as catalyst, showed good plant growth promoting activity on Oryza sativa. Among the DIM derivatives synthesized 3c shows potent auxin like growth promoting activity.