52562-50-2

Usage

Uses

Used in Chemical Synthesis:
5-METHYLINDOLE-3-CARBOXALDEHYDE is used as a reagent for the regioand enantioselective preparation of N-alkylated indoleand pyrrole-3-carbaldehydes. Its ability to selectively form desired products with specific stereochemistry makes it a valuable tool in the synthesis of complex organic molecules.
Used in Coordination Chemistry:
5-METHYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of novel flexible tripodal ligands derived from 3-methylindole. These ligands can form mononuclear complexes with various metal ions, such as Zn(II), Cu(II), Ni(II), Hg(II), and Pd(II). These complexes have potential applications in various fields, including catalysis, sensing, and materials science.
Used in Pharmaceutical Industry:
5-METHYLINDOLE-3-CARBOXALDEHYDE can be used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a promising candidate for the development of new drugs with novel therapeutic properties.
Used in Materials Science:
The metal complexes formed using 5-METHYLINDOLE-3-CARBOXALDEHYDE as a ligand can be used in the development of advanced materials with specific properties, such as conductivity, magnetism, or luminescence. These materials can find applications in various fields, including electronics, sensors, and energy storage.

InChI:InChI=1/C10H9NO/c1-7-2-3-10-9(4-7)8(6-12)5-11-10/h2-6,11H,1H3

Upstream product

• 109-94-4 formic acid ethyl ester 
• 30218-58-7 N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine 
• 614-96-0 5-methyl-1H-indole 
• 298-12-4 Glyoxilic acid 
• 50-00-0 formaldehyd 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 100-61-8 N-methylaniline 
• 68-12-2 N,N-dimethyl-formamide 
• 67-66-3 chloroform 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 122284-60-0 5-methyl-N-tosylindole-3-carboxaldehyde 
• 879375-37-8 benzyl-(5-methyl-1H-indol-3-ylmethyl)-amine 
• 879375-52-7 4-[benzyl-(5-methyl-1H-indol-3-ylmethyl)-amino]-but-2-en-1-ol 
• 879375-62-9 carbonic acid 4-[benzyl-(5-methyl-1H-indol-3-ylmethyl)-amino]-but-2-enyl ester methyl ester 
• 879375-44-7 4-[benzyl-(5-methyl-1H-indol-3-ylmethyl)-amino]-but-2-enoic acid ethyl ester 
• 194490-13-6 5-methyl-1H-indole-3-carbonitrile 
• 1352562-84-5 3,4,5-trihydroxy-N'-[(5-methyl-1H-indol-3-yl)methylidene]benzohydrazide 
• 1521625-26-2 N-butyl-5-methylindole-3-carboxaldehyde 
• 608-05-9 5-methyl-indole-2,3-dione 
• 65881-14-3 2-(5-methyl-1H-indol-3-yl)acetonitrile 

Relevant academic research and scientific papers

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Structural Rigidification of N-Aryl-pyrroles into Indoles Active against Intracellular and Drug-Resistant Mycobacteria

A series of indolyl-3-methyleneamines incorporating lipophilic side chains were designed through a structural rigidification approach and synthesized for investigation as new chemical entities against Mycobacterium tuberculosis (Mtb). The screening led to the identification of a 6-chloroindole analogue 7j bearing an N-octyl chain and a cycloheptyl moiety, which displayed potent in vitro activity against laboratory and clinical Mtb strains, including a pre-extensively drug-resistant (pre-XDR) isolate. 7j also demonstrated a marked ability to restrict the intracellular growth of Mtb in murine macrophages. Further assays geared toward mechanism of action elucidation have thus far ruled out the involvement of various known promiscuous targets, thereby suggesting that the new indole 7j may inhibit Mtb via a unique mechanism.

Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity

Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F420 in these strains. Complementation experiments showed that F420-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F420 were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F420-dependent enzyme in mycobacteria.

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.

Annulative π-Extension (APEX) of Indoles to Pyrido[1,2- a]indoles Using 4-Oxo Peroxides as C4 Units

Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Br?nsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature.

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst

A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.

Potassium-ion competitive acid blocker containing indole structure and preparation method and application of potassium-ion competitive acid blocker

The invention discloses an indole derivative or a pharmaceutically acceptable salt thereof and particularly relates to a compound containing a 1-sulfonyl-3-alkylamino methyl indole structure. The compound is shown as a formula I. The invention also discloses a preparation method of the indole derivative and application of the indole derivative in preparation of a potassium-ion competitive acid blocker or a drug for treating acid-related diseases. The preparation method has the advantages of being simple and high in yield and reproducibility.