1136-87-4

Usage

Uses

Used in Sleep Regulation:
2-METHYL-1H-INDOLE-3-PROPANOIC ACID is used as a sleep aid for managing sleep disorders, jet lag, and other related issues. It helps regulate the body's internal clock and promotes a healthy sleep-wake cycle.
Used in Antioxidant Therapy:
2-METHYL-1H-INDOLE-3-PROPANOIC ACID is used as an antioxidant to protect cells from damage caused by free radicals. Its antioxidant properties contribute to the maintenance of overall health and well-being.
Used in Mood Regulation:
2-METHYL-1H-INDOLE-3-PROPANOIC ACID is used as a mood enhancer, potentially improving mood and reducing symptoms of depression and anxiety.
Used in Hormone Regulation:
2-METHYL-1H-INDOLE-3-PROPANOIC ACID is used as a hormone regulator, helping to maintain optimal hormone levels and balance in the body.
Used in Pharmaceutical Industry:
2-METHYL-1H-INDOLE-3-PROPANOIC ACID is used as an active ingredient in supplements and medications for various health-related applications, including sleep regulation, antioxidant therapy, mood regulation, and hormone regulation. Its versatile properties make it a valuable component in the development of health products.

InChI:InChI=1/C12H13NO2/c1-8-9(6-7-12(14)15)10-4-2-3-5-11(10)13-8/h2-5,13H,6-7H2,1H3,(H,14,15)

Upstream product

• 1079-30-7 3-(2-cyanoethyl)-2-methylindole 
• 95-20-5 2-methyl-1H-indole 
• 57-57-8 β-Propiolactone 
• 40641-04-1 ethyl 3-(2-methylindol-3-yl)propionate 
• 92647-35-3 3,3'-(2-methyl-indole-1,3-diyl)-di-propionic acid 
• 3740-59-8 3,4-dihydro-6-methyl-2H-pyran-2-one 
• 59-88-1 phenylhydrazine hydrochloride 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 3128-06-1 5-ketohexanoic acid 
• 100-63-0 phenylhydrazine 
• 5636-66-8 6-methylidenetetrahydro-2-pyrone 
• 41143-12-8 hex-4-ynoic acid 
• 53293-00-8 hex-5-ynoic acid 

Downstream Products

• 239076-88-1 N-[(S)-1-benzyl-2-hydroxyethyl]-3-(2'-methyl-indol-3'-yl)propionamide 
• 34597-98-3 1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine 
• 34609-83-1 3-(2-methyl-1H-indol-3-yl)propan-1-ol 
• 239076-91-6 (S)-4-benzyl-2-[2-(2'-methyl-indol-3'-yl)ethyl]-2-oxazoline 

Relevant academic research and scientific papers

A General Synthesis of Substituted Indoles from Cyclic Enol Ethers and Enol Lactones

(Equation presented) A general method was developed for the one-pot synthesis of highly functionalized indoles from simple, commercially available aryl hydrazines and cyclic enol ethers. Enol lactones were also used as substrates, affording substituted indole acetic acid or indole propionic acid derivatives. This procedure affords 2,3-disubstituted indoles as single regioisomers from the appropriately substituted enol ether or enol lactone. This method was highlighted in the efficient synthesis of the antimigraine drug sumitriptan and the antiinflammatory drug indomethacin.

CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)

The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.

Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity

Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6.

Mechanistic dichotomy with alkynes in the formal hydrohydrazination/Fischer indolization tandem reaction catalyzed by a Ph3PAuNTf 2/pTSA binary system

An efficient method involving a formal hydrohydrazination/Fischer indolization tandem reaction to synthesize 2,3-disubstituted indoles from alkynes and arylhydrazines has been developed. The approach uses a Ph 3PAuNTf2/pTSA·H2O binary catalytic system in which a very low catalyst loading of Ph3PAuNTf2 (2 mol-%) is required. The reaction time is very short and, most importantly, the reaction is not sensitive to moisture. The mechanism of these reactions has been investigated and the results led us to propose an interesting mechanistic dichotomy. When alkynes have OH/COOH groups in the tether, hydroalkoxylation/ hydrocarboxylation occurred to generate exocyclic enol ethers/lactones that reacted with hydrazines to produce indoles. In cases where the alkynes lack OH/COOH groups, hydration occurs to generate ketones that react with arylhydrazines to give the desired indoles. A method for the synthesis of 2,3-disubstituted indoles from alkynes and arylhydrazines is reported that utilizes a Ph3PAuNTf2/pTSA·H2O binary catalytic system. Mechanistic aspects including an alkyne-dependant dichotomy is also discussed. Copyright

Solvolyses of 2-Deoxy-α- and β-D-Glucopyranosyl 4′-Bromoisoquinolinium Tetrafluoroborates

The solvolyses of 2-deoxy-α- and β-D-glucopyranosyl 4′-bromoisoquinolinium tetrafluoroborates (1 and 2) were monitored in aqueous methanol, ethanol, trifluoroethanol, and binary mixtures of ethanol and trifluoroethanol. The observed rate constants are consistent with the solvolyses of 1 and 2 proceeding via dissociative (DN * AN) transition states. In comparison to the α-anomer, solvolysis of the β-compound gives a greater transition state charge delocalization onto the ring oxygen atom. Analysis of the solvolysis product ratios indicates that the 2-deoxyglucosyl oxacarbenium ion is not solvent-equilibrated in the solvent mixtures studied. In the solvolysis of compound 1, the solvent trifluoroethanol facilitates diffusional separation of the leaving group and, in so doing, promotes the formation of the retained trifluoroethyl glycoside.