90734-97-7

Usage

Uses

Used in Food Safety and Human Health Research:
4-Methoxyindole-3-carboxaldehyde is used as a research subject for understanding its role as a nitrosatable mutagen precursor in Chinese cabbage. Studying 4-Methoxyindole-3-carboxaldehyde helps in identifying potential risks associated with its presence in food and developing strategies to mitigate those risks for the benefit of human health.

InChI:InChI=1/C10H9NO2/c1-13-9-4-2-3-8-10(9)7(6-12)5-11-8/h2-6,11H,1H3

Upstream product

• 72527-73-2 4-iodo-indole-3-carboxaldehyde 
• 124-41-4 sodium methylate 
• 120-72-9 indole 
• 4837-90-5 4-methoxy-1H-indole 
• 100-97-0 hexamethylenetetramine 
• 2380-94-1 1H-indol-4-ol 
• 100-61-8 N-methylaniline 
• 79-37-8 oxalyl dichloride 
• 81038-38-2 4-iodo-1H-indole 
• 335451-26-8 3-bromo-4-methoxy-1-(triisopropylsilyl)-1H-indole 
• 335451-18-8 4-Methoxy-1-(triisopropylsilyl)indole 
• 135-02-4 ortho-anisaldehyde 
• 143702-35-6 (Z)-2-azido-3-(2-methoxyphenyl)acrylic acid methyl ester 
• 111258-23-2 methyl 4-methoxy-1H-indole-2-carboxylate 

Downstream Products

• 52335-75-8 (4-methoxy-1H-indol-3-ylmethyl)dimethylamine 
• 96888-16-3 3-hydroxymethyl-4-methoxyindole 
• 620175-74-8 4-methoxy-1-methyl-1H-indole-3-carbaldehyde 
• 3610-35-3 4-methoxytryptamine 
• 1202631-44-4 N-tert-butoxycarbonyl-4-methoxyindole-3-carboxaldehyde 
• 929083-72-7 4-methoxyindole-3-isothiocyanate 
• 6202-22-8 (+)-mitragynine 
• 6202-22-8 methyl (Z)-2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate 
• 4098-40-2 mitragynine 

Relevant academic research and scientific papers

Effect of 4-Methoxyindole-3-Carbinol on the proliferation of colon cancer cells in vitro, when treated alone or in combination with indole-3-Carbinol

Consumption of cruciferous vegetables and cancer prevention seem to be positively associated. We present an easy two-step synthesis for 4-methoxyindole-3-carbinol (4MeOI3C), the expected breakdown product of 4-methoxyglucobrassicin during ingestion. 4MeOI3C inhibited the proliferation of human colon cancer cells DLD-1 and HCT 116 with IC50 values of 116 μM and 96 μM, respectively, after 48 h in vitro, and is therefore a more potent inhibitor than indole-3-carbinol (I3C). 4MeOI3C and I3C combined in different molar ratios inhibited proliferation in a nearly additive to slightly synergistic manner. Proliferation was inhibited by 100 μM 4MeOI3C after 48 h without affecting cell cycle phase distribution, indicating an overall-slowdown effect on the cell cycle. However, 200 μM 4MeOI3C caused a very high level of cell death and an accumulation of living cells in the G0/G 1 phase, indicating a concentration-dependent mode of action. We conclude that 4MeOI3C might play a role in the cancer preventive effect of cruciferous vegetables.

Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are

Glucosinolates represent a large group of plant natural products long known for diverse and fascinating physiological functions and activities. Despite the relevance and huge interest on the roles of indole glucosinolates in plant defense, little is known about their direct interaction with microbial plant pathogens. Toward this end, the metabolism of indolyl glucosinolates, their corresponding desulfo-derivatives, and derived metabolites, by three fungal species pathogenic on crucifers was investigated. While glucobrassicin, 1-methoxyglucobrassicin, 4-methoxyglucobrassicin were not metabolized by the pathogenic fungi Alternaria brassicicola, Rhizoctonia solani and Sclerotinia sclerotiorum, the corresponding desulfo-derivatives were metabolized to indolyl-3-acetonitrile, caulilexin C (1-methoxyindolyl-3-acetonitrile) and arvelexin (4-methoxyindolyl-3-acetonitrile) by R. solani and S. sclerotiorum, but not by A. brassicicola. That is, desulfo-glucosinolates were metabolized by two non-host-selective pathogens, but not by a host-selective. Indolyl-3-acetonitrile, caulilexin C and arvelexin were metabolized to the corresponding indole-3-carboxylic acids. Indolyl-3-acetonitriles displayed higher inhibitory activity than indole desulfo-glucosinolates. Indolyl-3-methanol displayed antifungal activity and was metabolized by A. brassicicola and R. solani to the less antifungal compounds indole-3- carboxaldehyde and indole-3-carboxylic acid. Diindolyl-3-methane was strongly antifungal and stable in fungal cultures, but ascorbigen was not stable in solution and displayed low antifungal activity; neither compound appeared to be metabolized by any of the three fungal species. The cell-free extracts of mycelia of A. brassicicola displayed low myrosinase activity using glucobrassicin as substrate, but myrosinase activity was not detectable in mycelia of either R. solani or S. sclerotiorum.

First Electrophilic Substitution of 4-Methoxyindole with Triethyl Orthoformate as an a1-Synthon

4-Methoxyindole (2) reacts with triethyl orthoformate (1a) under proton catalysis to yield the functionalized indoles 3a - 3e in dependence on the reaction conditions.The attack of the electrophile takes place regiospecifically at the 3-position of the indole 2.

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.

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.

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.

Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors

Lysine-specific demethylase 1 (LSD1), demethylase against mono- and di - methylated histone3 lysine 4, has emerged as a promising target in oncology. More specifically, it has been demonstrated as a key promoter in acute myeloid leukemia (AML), and several LSD1 inhibitors have already entered into clinical trials for the treatment of AML. In this paper, a series of new indole derivatives were designed and synthesized based on a lead compound obtained by a high-throughput screening with our in-house compound library. Among the synthetic compounds, 9e was characterized as a potent LSD1 inhibitor with an IC50 of 1.230 μM and can inhibit the proliferation of THP-1 cells effectively. And most importantly, this is the first irreversible LSD1 inhibitor that is not derived from monoamine oxidase inhibitors. Hence, the discovery of 9e may serve as a proof of concept work for AML treatment.

Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure

A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.

MITRAGYNINE ALKALOIDS AS OPIOID RECEPTOR MODULATORS

The present invention provides a compound having the structure: or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain, a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents

Sixteen new selenium-containing indole chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 25b exhibited the most potent antiproliferative activities against six human cancer cell lines with IC50 values of 0.004-0.022 μM. A microtubule dynamics assay and an immunofluorescence assay confirmed that 25b could effectively inhibit tubulin polymerization (IC50 = 2.1 ± 0.27 μM). Further cellular mechanism studies revealed that 25b induced G2/M phase arrest, which was further evidenced by the decrease in the mitochondrial membrane potential (MMP).