10601-19-1

Usage

Uses

1. Used in Pharmaceutical Industry:
5-Methoxyindole-3-carboxaldehyde is used as a reactant for the synthesis of tryptophan dioxygenase inhibitors, which have potential as anticancer immunomodulators. These inhibitors can modulate the immune system to fight cancer cells more effectively.
2. Used in Biochemical Research:
In the field of biochemistry, 5-Methoxyindole-3-carboxaldehyde serves as a reactant in the preparation of inhibitors for the C-terminal domain of RNA polymerase II. These inhibitors play a crucial role in regulating gene expression and can be used to study the mechanisms of transcription.
3. Used in Chemical Synthesis:
5-Methoxyindole-3-carboxaldehyde is utilized as a reactant in the preparation of imidazopyridines and imidazobenzothiazoles, which are important compounds in the development of new drugs and materials.
4. Used in Neuroscience:
In the neuroscience field, 5-Methoxyindole-3-carboxaldehyde is used as a reactant in the preparation of fluorescent neuroactive probes. These probes are essential for brain imaging and can help researchers study the structure and function of the nervous system.
5. Used in Antimicrobial Applications:
5-Methoxyindole-3-carboxaldehyde is also used as a reactant in the preparation of antibacterial agents. These agents can be used to develop new antibiotics or disinfectants to combat bacterial infections.
6. Used in Endocrinology:
In the field of endocrinology, 5-Methoxyindole-3-carboxaldehyde is used as a reactant in the synthesis of antiandrogens. These compounds can help regulate hormone levels and are used in the treatment of various hormonal disorders.

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

Upstream product

• 77144-90-2 1,3-diacetyl-2-(5-methoxyindol-3-yl)-4-imidazoline 
• 1006-94-6 5-methoxylindole 
• 68-12-2 N,N-dimethyl-formamide 
• 67-66-3 chloroform 
• 117616-04-3 4-methoxy-2-trimethylsilylmethylbenzanilide 
• 109-94-4 formic acid ethyl ester 
• 75-50-3 trimethylamine 
• 16620-52-3 5-methoxygramine 
• 79-37-8 oxalyl dichloride 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 100-97-0 hexamethylenetetramine 
• 100-61-8 N-methylaniline 
• 5367-32-8 5-methoxy-2-nitrotoluene 
• 2581-34-2 3-methyl-4-nitrophenol 

Downstream Products

• 171734-78-4 1-<2-(2-bromophenyl)ethyl>-5-methoxy-1H-indole-3-carboxaldehyde 
• 324756-80-1 3-formyl-5-methoxy-indole-1-carboxylic acid tert-butyl ester 
• 651331-50-9 5-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 191846-77-2 4-amino-5-methoxy-1-methyl-1H-indole-3-carbaldehyde 
• 191846-76-1 5-methoxy-1-methyl-4-nitro-1H-indole-3-carbaldehyde 
• 77419-78-4 5-Methoxy-indole-3-carbinol 
• 842975-56-8 1-ethyl-5-methoxy-1H-indole-3-carboxaldehyde 
• 847851-60-9 C₂₂H₂₆N₂O₂ 
• 1631136-28-1 C₂₉H₃₂N₂O₂ 
• 145158-71-0 tegaserod 
• 886883-32-5 benzyl-(1-allyl-5-methoxy-1H-indol-3-ylmethylene)-amine 
• 176688-98-5 (1-methyl-5-methoxy-1H-indol-3-yl)acetonitrile 
• 20731-70-8 5-methoxy-α-methyltryptamine 

Relevant academic research and scientific papers

Synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues

Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b-1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a-4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC50 0.24 μM).

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.

Intramolecular Diels-Alder reaction for the synthesis of tetracyclic carbazoles and isocanthines

One pot intramolecular Diels-Alder reaction has been efficiently used as a new route for the synthesis of four tetracyclic carbazoles and four isocanthine analogues where a dialdehyde is utilised as a common intermediate for both the scaffolds. Biological activity was evaluated for some molecules, which demonstrated moderate activity against HeLa cervical cancer cell lines.

Mapping the melatonin receptor. 7. Subtype selective ligands based on β-substituted N-acyl-5-methoxytryptamines and β-Substituted N-acyl-5-methoxy-1-methyltryptamines

A series of β-substituted and β,β-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxytryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT1 and MT2 receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores, β-Methylmelatonin (17a) and β,β-dimethylmelatonin (17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus, N-Butanoyl 5-methoxy-1-methyl-β,β-trimethylenetryptamine (12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-β,β-tetramethylenetryptamine (13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

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.

Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents

A series of novel chalcone analogues were designed, synthesized and evaluated as anticancer agents. The results of antiproliferative activity tests showed that most of the analogues exhibited moderate to very good antiproliferative activities with GI50 values in the micromol to sub-micromol range. Especially compound 10a gave 0.026 μM to 0.035 μM GI50 for five cancer cell lines. The mechanistic studies including tubulin polymerization inhibition, disruption of microtubule dynamics and cell cycle arrest assay demonstrated that compound 10a could effectively inhibit in vitro cellular tubulin polymerization, interfere with the mitosis, resulting in a prolonged G2/M cell cycle arrest and ultimately lead to cell apoptosis of cancer cells. Taken together, these results suggested that 10a may became a promising lead compound for development of new anticancer drugs.

Design, synthesis and biological evaluation of pyridine-chalcone derivatives as novel microtubule-destabilizing agents

Further optimization of the trimethoxyphenyl scaffold of parent chalcone compound (2a) by introducing a pyridine ring afforded a series of novel pyridine-chalcone derivatives as potential anti-tubulin agents. All the target compounds were evaluated for their antiproliferative activities. Among them, representative compound 16f exhibited the most potent activity with the IC50 values ranging from 0.023 to 0.045 μM against a panel of cancer cell lines. Further mechanism study results demonstrated that compound 16f effectively inhibited the microtubule polymerization by binding to the colchicine site of tubulin. Moreover, cellular mechanism studies disclosed that 16f caused G2/M phase arrest, induced cell apoptosis and disrupted the intracellular microtubule network. Also, 16f reduced the cell migration and disrupted the capillary-like tube formation of human umbilical vein endothelial cells (HUVECs). Importantly, 16f significantly inhibited tumor growth in H22 xenograft models without apparent toxicity, which was stronger than the reference compound CA-4, indicating that it is worthy to investigate 16f as a potent microtubule-destabilizing agent for cancer therapy.

Design, synthesis, and biological evaluation of NAD(P)H: Quinone oxidoreductase (NQO1)-targeted oridonin prodrugs possessing indolequinone moiety for hypoxia-selective activation

The enzyme NQO1 is a potential target for selective cancer therapy due to its overexpression in certain hypoxic tumors. A series of prodrugs possessing a variety of cytotoxic diterpenoids (oridonin and its analogues) as the leaving groups activated by NQO1 were synthesized by functionalization of 3-(hydroxymethyl)indolequinone, which is a good substrate of NQO1. The target compounds (29a-m) exhibited relatively higher antiproliferative activities against NQO1-rich human colon carcinoma cells (HT-29) and human lung carcinoma (A549) cells (IC50?=?0.263–2.904?μM), while NQO1-defficient lung adenosquamous carcinoma cells (H596) were less sensitive to these compounds, among which, compound 29h exhibited the most potent antiproliferative activity against both A549 and HT-29?cells, with IC50 values of 0.386 and 0.263?μM, respectively. Further HPLC and docking studies demonstrated that 29h is a good substrate of NQO1. Moreover, the investigation of anticancer mechanism showed that the representative compound 29h affected cell cycle and induced NQO1 dependent apoptosis through an oxidative stress triggered mitochondria-related pathway in A549?cells. Besides, the antitumor activity of 29h was also verified in a liver cancer xenograft mouse model. Biological evaluation of these compounds concludes that there is a strong correlation between NQO1 enzyme and induction of cancer cell death. Thus, this suggests that some of the target compounds activated by NQO1 are novel prodrug candidates potential for selective anticancer therapy.

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3

A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives

In this study, novel (E)-3-(5-substituted-1H-indol-3-yl)-1-(5,5,8,8- tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one (5(a-e)) derivatives were synthesized and their anticancer effects were determined in vitro. Novel indole retinoid compounds except 5e have anti-proliferative capacity in liver, breast and colon cancer cell lines. This anti-proliferative effect was further analyzed in breast cancer cell line panel by using the most potent compound 5a. It was determined that 5a can inhibit proliferation at very low IC50 concentrations in all of the breast cancer cell lines. Here, we present some evidence on apoptotic termination of cancer cell proliferation which may be primarily driven by the inhibition of RXRα and, to a lesser extent, RXRγ.