25119-60-2

Upstream product

• 37465-51-3 benzylidene-[2-(5-methoxy-indol-3-yl)-ethyl]-amine 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 100-52-7 benzaldehyde 
• 61675-19-2 5-methoxy-3-(2-nitroethylenyl)-1H-indole 
• 1006-94-6 5-methoxylindole 

Downstream Products

• 169120-76-7 (2-Benzyl-6-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-acetic acid methyl ester 
• 1366416-31-0 N-allyl-N-benzyl-(5-methoxy)tryptamine 
• 1391572-08-9 methyl 3-(benzyl(2-(5-methoxy-1H-indol-3-yl)ethyl)amino)-3-oxopropanoylcarbamate 
• 1432581-92-4 3-benzyl-10-methoxy-6-methyl-2,3-dihydro-1H-azocino[5,4-b]indol-4(7H)-one 
• 1432581-93-5 3-benzyl-10-methoxy-6-phenyl-2,3-dihydro-1H-azocino[5,4-b]indol-4(7H)-one 
• 86293-40-5 10-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one 
• 86293-41-6 10-hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one 

Relevant academic research and scientific papers

Design and synthesis of C10 modified and ring-truncated canthin-6-one analogues as effective membrane-active antibacterial agents

A series of canthin-6-one analogues were designed and synthesized in order to study their antibacterial activity and structure–activity relationships. Compound 22 showed a broad spectrum of antibacterial activity and exhibited better bactericidal effect (

Synthesis and in vitro antibacterial activity of quaternized 10-methoxycanthin-6-one derivatives

Background: Based on our previous work, we found that 10-methoxycanthin-6-one displayed potential antibacterial activity and quaternization was an available method for increasing the antibacterial activity. Here, we explored the antibacterial activity of quaternized 10-methoxy canthin-6-one derivatives. Methods and Results: Twenty-two new 3-N-benzylated 10-methoxy canthin-6-ones were designed and synthesized through quaternization reaction. The in vitro antibacterial activity against three bacteria was evaluated by the double dilution method. Moreover, the structure–activity relationships (SARs) were carefully summarized in order to guide the development of antibacterial canthin-6-one agents. Two highly active compounds (6p and 6t) displayed 8-fold superiority (MIC = 3.91 μg/mL) against agricultural pathogenic bacteria R. solanacearum and P. syringae compared to agrochemical streptomycin sulfate, and showed potential activity against B. cereus. Moreover, these two compounds exhibited good “drug-like” properties, low cytotoxicity, and no inhibition on seed germination. Conclusions: This work provides two new effective quaternized canthin-6-one derivatives as candidate bactericide, promoting the development of natural-sourced bactericides and preservatives.

Synthesis and evaluation of ester derivatives of 10-hydroxycanthin-6-one as potential antimicrobial agents

As part of our continuing research on canthin-6-one antimicrobial agents, a new series of ester derivatives of 10-hydroxycanthin-6-one were synthesized using a simple and effective synthetic route. The structure of each compound was characterized by NMR, ESI-MS, FT-IR, UV, and elemental analysis. The antimicrobial activity of these compounds against three phytopathogenic fungi (Alternaria solani, Fusarium graminearum, and Fusarium solani) and four bacteria (Bacillus cereus, Bacillus subtilis, Ralstonia solanacearum, and Pseudomonas syringae) were evaluated using the mycelium linear growth rate method and micro-broth dilution method, respectively. The structure-activity relationship is discussed. Of the tested compounds, 4 and 7s displayed significant antifungal activity against F. graminearum, with inhibition rates of 100% at a concentration of 50 μg/mL. Compounds 5, 7s, and 7t showed the best inhibitory activity against all the tested bacteria, with minimum inhibitory concentrations (MICs) between 3.91 and 31.25 μg/mL. Thus, 7s emerged as a promising lead compound for the development of novel canthine-6-one antimicrobial agents.

Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow

A metal-free, phosphine-catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.

Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: A metal-catalyzed variation on the Pictet-Spengler theme

An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile. The Royal Society of Chemistry 2012.

Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation

An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted

Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

A structure-activity relationship study was conducted on a series of tetrahydro-β-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNFα production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity.

Meisenheimer rearrangement of azetopyridoindoles. VIII. Synthesis and antiviral activities of 12-carbaeudistomin analogs

Eudistomins, isolated from the colonial tunicate Eudistoma olivaceum, have been a synthetic target due to their strong antiviral activity against Herpes simplesx virus (HSV-1) and activities against certain types of tumors in vivo. In order to examine the