2426-19-9

Usage

Uses

Used in Pharmaceutical Research:
5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE is used as a synthetic intermediate for the production of 5-Methoxy-N-methyl-N-isopropyl Tryptamine (M271680), a psychedelic tryptamine. 5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE is of interest to researchers due to its potent inhibition of serotonin and norepinephrine re-uptake, which may provide insights into the development of novel treatments for various psychiatric and neurological disorders.
Used in Forensic Applications:
In the field of forensic science, 5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE is utilized for the analysis and identification of synthetic tryptamines, particularly M271680. 5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE can be used as a reference material to help forensic chemists detect and characterize these substances in criminal investigations.
Used in Neurochemical Research:
5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE is used as a research tool to study the effects of M271680 on monoamine neurotransmitter systems. Its ability to inhibit the re-uptake of serotonin and norepinephrine without affecting dopamine re-uptake makes it a valuable compound for understanding the complex interactions between these neurotransmitters and their role in various physiological and pathological processes.
Used in Drug Development:
Although not directly used as a drug itself, 5-METHOXY-ALPHA-OXO-1H-INDOLE-3-ACETYL CHLORIDE plays a crucial role in the development of new pharmaceuticals targeting the monoamine system. By understanding the structure-activity relationships of compounds like M271680, researchers can design more effective and selective drugs for the treatment of conditions such as depression, anxiety, and other mood disorders.

InChI:InChI=1/C11H8ClNO3/c1-16-6-2-3-9-7(4-6)8(5-13-9)10(14)11(12)15/h2-5,13H,1H3

Upstream product

• 1006-94-6 5-methoxylindole 
• 79-37-8 oxalyl dichloride 
• 60-29-7 diethyl ether 

Downstream Products

• 97529-62-9 2-[2-(5-Methoxy-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid ethyl ester 
• 119284-52-5 N-[2-(3,4-Dihydroxy-phenyl)-ethyl]-2-(5-methoxy-1H-indol-3-yl)-2-oxo-acetamide 
• 94732-36-2 (S)-2-[2-(5-Methoxy-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid ethyl ester 
• 122334-70-7 (R)-2-[2-(5-Methoxy-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid ethyl ester 
• 134937-85-2 N-(2,6-Dichloro-phenyl)-2-(5-methoxy-1H-indol-3-yl)-2-oxo-acetamide 
• 52055-22-8 2-(5-methoxy-1H-indol-3-yl)-2-oxo-acetamide 
• 99988-56-4 methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate 
• 1061717-17-6 4β-((5-methoxy-indol-3-yl)-glyoxylamide)-4-desoxypodophyllotoxin 
• 1134099-88-9 1-(4-benzylpiperidin-1-yl)-2-(5-methoxy-1H-indol-3-yl)ethane-1,2-dione 
• 1415412-54-2 C₂₅H₂₉NO₇ 
• 23304-48-5 (5-methoxy-1H-indol-3-yl)acetic acid methyl ester 
• 3471-31-6 5-methoxy-1H-indole-3-acetic acid 
• 1067133-53-2 C₂₄H₂₈O₄N₂ 

Relevant academic research and scientific papers

A one-pot tandem Pictet-Spengler-Diels-Alder synthesis of apoyohimbines from 3-carbomethoxy-2-(formylmethyl)-3-sulfolene

Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, die products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation.

AZETIDINYL TRYPTAMINES AND METHODS OF TREATING PSYCHIATRIC DISORDERS

The present disclosure includes azetidinyl tryptamines and methods of treating psychiatric disorders with such compounds. Also provided are pharmaceutical compositions that include azetidinyl tryptamines.

PHARMACEUTICAL COMPOSITION COMPRISING 5-METHOXY-N, N-DIMETHYLTRYPTAMINE

An intranasal composition comprises a dosage amount of 50 to 150 mg / ml of 5-methoxy-N, N-dimethyltryptamine (5 MeODMT) in a liquid medium, 5MeODMT being formulated as a chloride salt of 5MeODMT (chlrorhydrate of 5MeODMT) and hydrochloride of 5MeODMT bei

Fe-Catalyzed Pictet-Spengler-Type Cyclization via Selective Four-Electron Reductive Functionalization of CO2

Herein, we describe a novel catalytic Pictet-Spengler-type cyclization using CO2 as a nontoxic and sustainable C1 feedstock with environmentally benign and non-precious-metal iron as catalyst. The reaction is achieved by selective four-electron reduction of CO2 into methylene level intermediate through carefully tuning the reaction parameters. A variety of tetrahydro-β-carbolines and other nitrogen-containing heterocycles can be easily obtained under mild conditions. Mechanistic studies have shown that tetrahydro-β-carbolines are probably obtained via spiroindolenine intermediates.

2-(1H-INDOLE-3-CARBONYL)-THIAZOLE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

2-(1H-lndole-3-carbonyl)-thiazole-4-carboxamide derivatives and the corresponding imidazole, oxazole and thiophene derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders. The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 27 to 32 and 59 to 219; examples 1 to 8; compounds 1-1 to 1-97; tables 1-a, 2 and 3).

Synthesis and anti-tumor activity of marine alkaloids

Marine alkaloids were divided into five categories from the perspective of anti-tumor activity. The optimization process, chemical synthesis, anti-tumor activity evaluation and structure–activity relationship of various compounds were discussed.

Design, synthesis, and evaluation of novel anti-trypanosomal compounds

Human African trypanosomiasis (HAT) is a deadly neglected tropical disease caused by the protozoan parasite Trypanosoma brucei. During the course of screening a collection of diverse nitrogenous heterocycles, we discovered two novel compounds that contain the tetracyclic core of the Yohimbine and Corynanthe alkaloids, were potent inhibitors of T. brucei proliferation and T. brucei methionyl-tRNA synthetase (TbMetRS) activity. Inspired by these key findings, we prepared several novel series of hydroxyalkyl δ-lactam, δ-lactam, and piperidine analogs and tested their anti-trypanosomal activity. A number of inhibitors were more potent against T. brucei than these initial hits with one hydroxyalkyl δ-lactam derivative being 25-fold more effective in our assay. Surprisingly, most of these active compounds failed to inhibit TbMetRS. This work underscores the importance of verifying, irrespective of close structural similarities, that new compounds designed from a lead with a known biological target engage the putative binding site.

Design, synthesis, evaluation, and molecular modeling studies of indolyl oxoacetamides as potential pancreatic lipase inhibitors

A series of indolyl oxoacetamide analogs was synthesized, characterized, and evaluated for their pancreatic lipase inhibitory activity using porcine pancreatic lipase (type II) and 4-nitrophenyl butyrate. Compound 8d exhibited a potent inhibition, with an IC50 value of 4.53 μM, followed by 8c (IC50 = 5.12 μM), compared with the standard drug, orlistat (IC50 = 0.99 μM). Furthermore, analogs 8c and 8d exhibited a reversible competitive inhibition, similar to orlistat. Molecular docking studies of the compounds 7a–f and 8a–f were in agreement with the in vitro results, wherein 8d exhibited a potential MolDock score of ?163.052 kcal/mol. A 10-ns molecular dynamics simulation of 8d complexed with pancreatic lipase confirmed the role of π–π stacking and π–cation interactions with the lid domain and Arg 256, respectively, in stabilizing the ligand at the active site (maximum observed root mean square deviation ≈ 2 ?). The present study led to the identification of novel indolyl oxoacetamides (8a–d) as potential pancreatic lipase inhibitory leads that might further result in enhanced potency through lead optimization.

ARYL HYDROCARBON RECEPTOR MODULATOR

Disclosed is an aryl hydrocarbon receptor modulator of formula (I), and a pharmaceutically acceptable salt thereof, wherein R′ is H, CN, CH2(OH)R0, CmH2m+1, CnH2n-1, CnH2n-3, two Ra are independently H or two Ra together form ═O or ═N—W3—R1; A is a C6 to C10 aromatic ring unsubstituted or substituted with 1 to 3 R, or a C2-C10 heteroaromatic ring interrupted by 1 to 5 heteroatoms selected from N, O, and S or a 4 to 7 membered nonaromatic heterocyclic ring containing C═N and interrupted by 1 to 3 heteroatoms selected from N, O, and S, with either one unsubstituted or substituted with 1 to 3 R; Q is R, or is a C6 to C10 aromatic ring or a C2 to C10 heteroaromatic ring unsubstituted or substituted with 1 to 3 R and interrupted by 1 to 5 heteroatoms selected from N, O, and S; and R is Rc which is C-attached or RN which is N-attached. The compounds of formula (I) of the present invention can regulate AhR activity, and can be used to inhibit the growth of cancer cells and inhibit the metastasis and invasion of tumor cells.

Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities

A series of bis(indolyl)glyoxylamides 10a-n has been designed and synthesized. In situ generated indole-3-glyoxalylchloride from the reaction of readily available indole 9 with oxalyl chloride was treated with tryptamine to produce bis(indolyl)glyoxylamides 10a-n in 82-93% yields. All the synthesized bis(indolyl)glyoxylamides were well characterized and tested for their antibacterial activity against Gram-positive and Gram-negative bacterial strains. Compounds 10d, 10g and 10i were found to display potent antibacterial activity against Gram-negative strain. Further, the cytotoxicity of bis(indolyl)glyoxylamides 10a-n were evaluated against a panel of human cancer cell lines. Of the screened analogues, compound 10f (IC50 = 22.34 μM; HeLa, 24.05 μM; PC-3, 21.13 μM; MDA-MB-231 and 29.94 μM; BxPC-3) was identified as the most potent analogue of the series. Exposure of PC-3 cells to either 10a or 10f resulted in increased levels of cleaved PARP1, indicating that bis(indolyl)glyoxylamides induce apoptosis in PC-3 cells. Most importantly, compounds 10d, 10g and 10i were completely ineffective in mammalian cells, suggesting that they target bacterial-specific targets and thus will not display any toxicity in host cells.