16381-50-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-3-Methyl-1H-Indole-2-carboxylic Acid is used as an antispasmodic agent for the treatment of various gastrointestinal disorders. Its antispasmodic properties help in reducing muscle spasms and pain associated with conditions like irritable bowel syndrome and inflammatory bowel disease.
Used in Chemical Industry:
5-Methoxy-3-Methyl-1H-Indole-2-carboxylic Acid is used in the preparation of oxazinones, which are potential bactericides. These oxazinones can be employed as antimicrobial agents in various applications, such as in the development of new antibiotics or as preservatives in different products.
Additionally, 5-Methoxy-3-Methyl-1H-Indole-2-carboxylic Acid is used in the synthesis of monoamine oxidase inhibitors. These inhibitors play a crucial role in the treatment of various psychiatric and neurological disorders, such as depression, anxiety, and Parkinson's disease, by regulating the levels of monoamines in the brain.

InChI:InChI=1/C11H11NO3/c1-6-8-5-7(15-2)3-4-9(8)12-10(6)11(13)14/h3-5,12H,1-2H3,(H,13,14)

Upstream product

• 16381-42-3 ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate 
• 36820-78-7 3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester 
• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 30464-90-5 5-methoxy-3-methyl-1Hindole-2-carbaldehyde 
• 600136-03-6 (6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate 
• 600136-02-5 2-ethoxycarbonyl-3-benzyl-9-methoxy-1,2,3,3a,4,5-hexahydrocanthin-6-one 
• 600135-96-4 N_b-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester 
• 600136-09-2 tert-butyl 3-(Hydroxymethyl)-5-methoxy-1H-indole-1-carboxylate 
• 409095-10-9 trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester 
• 600135-99-7 (6S,10S)-methyl-2-methoxy-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate 
• 600136-00-3 C₂₃H₂₄N₂O₂ 
• 171018-94-3 (3S,6R)-6-(1-benzenesulfonyl-5-methoxy-3-indolyl)-methyl-3,6-dihydro-3-isopropyl-2,5-diethoxypyrazine 
• 171820-27-2 1-tert-butyloxycarbonyl-N_b-benzyl-5-methoxytryptophan ethyl ester 
• 168143-73-5 1-benzenesulfonyl-3-bromomethyl-5-methoxyindole 
• 168143-69-9 5-methoxy-3-methyl-1-(phenylsulfonyl)-1H-indole 

Relevant academic research and scientific papers

Development of potent dipeptide-type SARS-CoV 3CL protease inhibitors with novel P3 scaffolds: Design, synthesis, biological evaluation, and docking studies

We report the design and synthesis of a series of dipeptide-type inhibitors with novel P3 scaffolds that display potent inhibitory activity against SARS-CoV 3CLpro. A docking study involving binding between the dipeptidic lead compound 4 and 3CLpro suggested the modification of a structurally flexible P3 N-(3-methoxyphenyl)glycine with various rigid P3 moieties in 4. The modifications led to the identification of several potent derivatives, including 5c-k and 5n with the inhibitory activities (Ki or IC50) in the submicromolar to nanomolar range. Compound 5h, in particular, displayed the most potent inhibitory activity, with a Ki value of 0.006 μM. This potency was 65-fold higher than the potency of the lead compound 4 (Ki = 0.39 μM). In addition, the Ki value of 5h was in very good agreement with the binding affinity (16 nM) observed in isothermal titration calorimetry (ITC). A SAR study around the P3 group in the lead 4 led to the identification of a rigid indole-2-carbonyl unit as one of the best P3 moieties (5c). Further optimization showed that a methoxy substitution at the 4-position on the indole unit was highly favorable for enhancing the inhibitory potency.

INDOLE DERIVATIVES AND THEIR USE AS THYROID RECEPTOR LIGANDS

The invention provides compounds of formula (I) or pharmaceutically acceptable esters, amides, solvates or salts thereof, including salts of such esters or amides, and solvates of such esters, amides or salts, (I) wherein R1, R2, R3, R4, R5, R6, Y and W are as defined in the specification. The invention also provides the use of such compounds in the treatment or prophylaxis of a condition that may be treated with a thyroid receptor agonist or partial agonist.

The enantiospecific, stereospecific total synthesis of the ring-A oxygenated sarpagine indole alkaloids (+)-majvinine, (+)-10-methoxyaffinisine, and (+)-Na-methylsarpagine, as well as the total synthesis of the Alstonia bisindole alkaloid macralstonidine

The first stereospecific, enantiospecific total synthesis of the ring-A oxygenated sarpagine indole alkaloids (+)-Na-methylsarpagine (8), (+)-majvinine (14), and (+)-10-methoxyaffinisine (49), as well as the first total synthesis of the Alstonia bisindole alkaloid macralstonidine (9), has been accomplished. This approach employed the Schoellkopf chiral auxiliary for the stereospecific construction of the desired D-(+)-tryptophan unit required for the asymmetric Pictet-Spengler reaction. In addition, the strategy was doubly convergent for the enolate-mediated Pd0 coupling process and the asymmetric Pictet-Spengler reaction can be employed to synthesize both macroline (2) and Na-methylsarpagine (8), the coupling of which provides macralstonidine (9). This approach to ring-A substituted alkoxyindole alkaloids should find wide application for the synthesis of other alkaloids for it is stereospecific and either enantiomer can be prepared with ease.

Enantiospecific synthesis of 5-methoxy-D(+)- or L(-) tryptophan

A method for the enantiospecific synthesis of 5-methoxy-D(+)-tryptophan 8 or the L(-)-optical antipode is described. This procedure can be scaled up and performed without the need for extensive chromatographic separations. It provides for the first time t