109021-59-2

Basic information

• Product Name: 7-Methoxy-3-indolecarboxaldehyde
• Synonyms: 7-METHOXY-3-INDOLECARBOXALDEHYDE;7-METHOXYINDOLE-3-CARBOXALDEHYDE;7-METHOXY-1H-INDOLE-3-CARBALDEHYDE;3-Formyl-7-methoxyindole;1H-Indole-3-carboxaldehyde, 7-methoxy-;7-methoxy-1H-Indole-3-carboxaldehyde
• CAS NO: 109021-59-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Product Categories: Indole;Building Blocks
• Mol File: 109021-59-2.mol

Chemical Properties

• Melting Point: 159-160 °C
• Boiling Point: 375.236 °C at 760 mmHg
• Flash Point: 180.736 °C
• Appearance: /
• Density: 1.274 g/cm³
• Vapor Pressure: 7.89E-06mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: 2-8°C
• PKA: 14.99±0.30(Predicted)
• CAS DataBase Reference: 7-Methoxy-3-indolecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-3-indolecarboxaldehyde(109021-59-2)
• EPA Substance Registry System: 7-Methoxy-3-indolecarboxaldehyde(109021-59-2)

Safety Data

• Hazardous Substances Data: 109021-59-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
7-Methoxy-3-indolecarboxaldehyde is used as a reactant for the preparation of [(indolyl)methyl]hydantoin and thiohydantoin derivatives. These compounds have potential applications in the treatment of necroptosis, a form of programmed cell death that occurs in response to various cellular stressors.
Used in Anticancer Applications:
7-Methoxy-3-indolecarboxaldehyde is also used as a reactant in the synthesis of pyridyl-ethenyl-indoles, which are potential anticancer immunomodulators. These compounds may help modulate the immune system to enhance the body's response against cancer cells, potentially leading to improved treatment outcomes for cancer patients.

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

Upstream product

• 3189-22-8 7-methoxy-1H-indole 
• 67-66-3 chloroform 
• 68-12-2 N,N-dimethyl-formamide 
• 591-31-1 3-methoxy-benzaldehyde 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 
• 84638-71-1 7-methoxy-1H-indole-2-carboxylic acid methyl ester 
• 24610-33-1 7-methoxy-1H-indole-2-carboxylic acid 

Downstream Products

• 812652-85-0 7-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 2436-18-2 2-(7-methoxy-1H-indol-3-yl)acetonitrile 
• 1631136-30-5 C₂₉H₃₂N₂O₂ 
• 1262643-16-2 1-benzyloxymethyl-5-methoxy-1H-indole-3-carbaldehyde 
• 2436-04-6 2-(7-methoxy-indol-3-yl)-ethylamine 
• 812653-09-1 16-[7-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]hexadecan-1-ol 

Relevant articles and documents

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.

CELL CYCLE PROGRESSION INHIBITOR

The present invention provides a cell cycle progression inhibitor, a cytostatic agent, and an anticancer agent. The cell cycle progression inhibitor, the cytostatic agent, and the anticancer agent each contains a Hes1 protein-PHB2 protein binding enhancer.

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.

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Chiral anion phase transfer of aryldiazonium cations: An enantioselective synthesis of C3-diazenated pyrroloindolines

Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core. Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99% yield and 96% ee (MTBE=methyl tert-butyl ether).

Silica-supported ceric ammonium nitrate catalyzed chemoselective formylation of indoles

Selective formylation of free (N-H) indoles at C3 can be achieved by using formylating species generated from hexamethylenetetramine (HMTA) and silica-supported ceric ammonium nitrate (CAN-SiO2). The use of a catalytic amount of this solid-supported reagent was found to be compatible with a range of substituents on the indoles and generated the corresponding products with good yields. A plausible mechanism for the formylation involving an electron transfer process is discussed.

Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.