104142-24-7

Upstream product

• 703-80-0 3-acetylindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 104142-15-6 2-methyl-1-tosyl-1H-indole-3-carbaldehyde 
• 120-72-9 indole 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 75-16-1 methylmagnesium bromide 
• 224434-80-4 2-bromo-1-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethanone 
• 65037-62-9 3-ethenyl-1-[(4-methylbenzene)sulfonyl]-1H-indole 
• 7677-24-9 trimethylsilyl cyanide 
• 701204-62-8 1-(1-tosyl-1H-indol-3-yl)ethan-1-ol 
• 487-89-8 Indole-3-carboxaldehyde 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 104142-15-6 2-methyl-1-tosyl-1H-indole-3-carbaldehyde 
• 224434-80-4 2-bromo-1-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethanone 
• 703-80-0 3-acetylindole 
• 904694-73-1 3-(α,α-dimethoxyethyl)-1-tosylindole 
• 875289-90-0 1-[(4-methylphenyl)sulfonyl]-3-{1-[(trimethylsilyl)oxy]ethenyl}-1H-indole 
• 19012-02-3 N-methyl-3-acetylindole 
• 866476-10-0 4-acetoxy-4-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-pent-2-ynoic acid ethyl ester 
• 904694-74-2 3-(α-methoxyvinyl)-1-tosylindole 
• 904694-90-2 3-(α-diethylphosphoryloxyvinyl)-1-tosylindole 

Relevant academic research and scientific papers

Cobalt-Catalyzed Regioselective Direct C-4 Alkenylation of 3-Acetylindole with Michael Acceptors Using a Weakly Coordinating Functional Group

Herein, we disclosed the first report on the selective C(4)-H functionalization of 3-acetylindole derivatives using first-row transition metal cobalt where an acetyl group is acting as a weakly coordinating directing group. Selective C(4)-H functionalization has been achieved using diverse Michael acceptors (acrylate and maleimide) simply by switching the additive from copper acetate to silver carbonate. Further the formation of a cobaltacycle intermediate was also detected through HRMS for mechanistic insight.

Optimization, Structure-Activity Relationship, and Mode of Action of Nortopsentin Analogues Containing Thiazole and Oxazole Moieties

Plant diseases seriously endanger plant health, and it is very difficult to control them. A series of nortopsentin analogues were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities. Most of these compounds displayed higher antiviral activities than ribavirin. Compounds 1d, 1e, and 12a, with excellent antiviral activities, emerged as novel antiviral lead compounds, among which 1e was selected for further antiviral mechanism research. The mechanism research results indicated that these compounds may play an antiviral role by aggregating viral particles to prevent their movement in plants. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad-spectrum fungicidal activities. Compounds 2p and 2f displayed higher antifungal activities against Alternaria solani than the commercial fungicides carbendazim and chlorothalonil. Current research has laid a foundation for the application of nortopsentin analogues in plant protection.

Niobium pentachloride-silver perchlorate as an efficient catalyst in the Friedel-Crafts acylation and Sakurai-Hosomi reaction of acetals

Friedel-Crafts acylation catalyzed by niobium pentachloride with silver salt is described. Aromatic compounds with Ac2O or Bz2O were smoothly converted into the corresponding ketones in good to excellent yields. This system was also applied to the Sakurai-Hosomi reaction using acetals. The reaction proceeded quite rapidly to give the desired products in excellent yields.

Simple N-Alkylation and N-Acylation of 3-Acetylindole and 3-Indolecarbaldehyde

Using lithium cyanide a simple method for the transformation of 3-acetylindole into the N-alkyl, N-acyl, and N-p-toluenesulfonyl derivatives in good yield is reported. 3-Indolecarbaldehyde is also N-alkylated by the same procedure.

InCl3 and In(OTf)3 catalyzed reactions: Synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives

Indium trichloride and indium triflate were found to be effective catalysts for the acetylation of indoles to 3-acetyl indoles and is reported for the first time in good yield. Indium triflate is also found to be an efficient catalyst for the synthesis of bis-indolylmethane and indolylquinoline derivatives.

Meridianin G and its analogs as antimalarial agents

The marine-derived indole alkaloids meridianin C and G and their N1-substituted and C-ring modified analogs were synthesized and screened for antiprotozoal and antimicrobial activities. Meridianin C and G showed antimalarial activity against both chloroquine-resistant (D6) as well as sensitive (W2) clones of Plasmodium falciparum with IC50 values in the range of 4.4 to 14.4 μM. Meridianin G showed better activity against the W2 clone, showing a higher selectivity index >24.1. Among the analogs, N1-morpholinoyl meridianin C analog displayed antimalarial activity against both clones, showing selectivity indices up to 25.1. Meridianin C along with a few other analogs showed weak to moderate antileishmanial activity against Leishmania donovani promastigotes, the best analog being a C-ring modified 5-iodo meridianin showing an IC50 of 9.17 μM. A few compounds also showed mild antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus, and antifungal activity against Cryptococcus neoformans.

Discovery of novel 4-azaaryl-N-phenylpyrimidin-2-amine derivatives as potent and selective FLT3 inhibitors for acute myeloid leukaemia with FLT3 mutations

Feline McDonough sarcoma (FMS)-like tyrosine kinase 3 (FLT3) is one of the most pursued targets in the treatment of acute myeloid leukaemia (AML) as its gene amplification and mutations, particularly internal tandem duplication (ITD), contribute to the pa

3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, nortopsentin Analogues with antiproliferative activity

A new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and the indole unit bound to position 2 of the thiazole ring was substituted by a 7-azaindole moiety, was efficiently synthesized. Two of t

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes

Chiral nitriles and their derivatives are prevalent in pharmaceuticals and bioactive compounds. Enantioselective alkene hydrocyanation represents a convenient and efficient approach for synthesizing these molecules. However, a generally applicable method featuring a broad substrate scope and high functional group tolerance remains elusive. Here, we address this long-standing synthetic problem using dual electrocatalysis. Using this strategy, we leverage electrochemistry to seamlessly combine two canonical radical reactions—cobalt-mediated hydrogen-atom transfer and copper-promoted radical cyanation—to accomplish highly enantioselective hydrocyanation without the need for stoichiometric oxidants. We also harness electrochemistry’s unique feature of precise potential control to optimize the chemoselectivity of challenging substrates. Computational analysis uncovers the origin of enantio-induction, for which the chiral catalyst imparts a combination of attractive and repulsive non-covalent interactions to direct the enantio-determining C–CN bond formation. This work demonstrates the power of electrochemistry in accessing new chemical space and providing solutions to pertinent challenges in synthetic chemistry. [Figure not available: see fulltext.]