30536-48-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Methoxyindoleacetonitrile is used as a precursor in the synthesis of biologically active molecules for various pharmaceutical applications due to its unique chemical structure and potential to be modified for specific therapeutic purposes.
Used in Anti-tumor Applications:
1-Methoxyindoleacetonitrile is used as an anti-tumor agent for its potential to inhibit the growth of cancer cells, making it a promising candidate for further research and development in oncology.
Used in Neurological Disorder Treatment:
1-Methoxyindoleacetonitrile is used in the treatment of neurological disorders due to its potential neuroprotective and therapeutic effects, which are currently under investigation for various conditions.
Used in Bioactive Compound Synthesis:
1-Methoxyindoleacetonitrile is used as a building block in the synthesis of various pharmaceuticals and bioactive compounds, leveraging its chemical properties to create new molecules with potential therapeutic applications.

Upstream product

• 91913-81-4 2-hydroxyimino-3-(1-methoxy-3-indolyl)propionic acid 
• 5187-84-8 1-methoxy-3-indolylmethyl glucosinolate 
• 54698-11-2 1-methoxyindole 
• 32991-03-0 trans-β-dimethylamino-2-nitrostyrene 
• 69111-76-8 1-methoxy-3-(2-nitrovinyl)indole 
• 91913-79-0 9-Methoxy-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indole-3-carboxylic acid ethyl ester 
• 91913-80-3 ethyl 2-hydroxyimino-3-(1-methoxy-3-indolyl)propionate 
• 3289-82-5 1-hydroxyindole 
• 771-51-7 indole-3-acetonitrile 
• 64802-55-7 2,3-dihydro-1H-indole-3-acetonitrile 
• 77-78-1 dimethyl sulfate 
• 98258-85-6 1-methoxy-3-(2-nitroethyl)indole 

Relevant academic research and scientific papers

The phytoalexins from cauliflower, caulilexins A, B and C: Isolation, structure determination, syntheses and antifungal activity

Our continuous search for phytoalexins from crucifers led us to examine phytoalexin production in florets of cauliflower (Brassica oleracea var. botrytis) under abiotic (UV light) elicitation. Four known (isalexin, S-(-)-spirobrassinin, 1-methoxybrassitin, brassicanal C) and three new (caulilexins A-C) phytoalexins were isolated. The syntheses and antifungal activity of caulilexins A-C against the economically important pathogenic fungi Leptosphaeria maculans, Rhizoctonia solani and Sclerotinia sclerotiorum, and the first synthesis of brassicanal C are reported.

Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates

Micellar electrokinetic capillary chromatography (MECC) was used to follow the myrosinase (β-thioglucoside glucohydrolase EC 3.2.3.1)-catalyzed transformation of glucobrassicin (indol-3-ylmethylglucosinolate, 1a) and neoglucobrassicin (N-methoxyglucobrassicin, 1b) into nitriles, ascorbigens, and other products. The influence of pH, ascorbic acid, and Fe(II) ions was investigated. In the presence of ascorbic acid, (5 mM), thiocyanate ion and ascorbigens were the dominating products from 1a and 1b. In the presence of Fe(II) ions (2.5 mM), nitriles were the dominating products between pH 4 and 6-7. During hydrolysis of 1b in neutral or weakly basic solution, an unstable intermediate was detected by MECC. Comparisons of the rate of ascorbigen formation from 1a, 1b, and indol-3-ylcarbinol showed that ascorbigens were formed directly from ascorbate and unstable products of the hydrolysis of indole glucosinolates and that indol-3-ylcarbinols were not important intermediates. Structures of 1a, 1b, and products of 1b were confirmed by 1H NMR, MS, and UV spectroscopy.

Chemistry of Indole Glucosinolates: Intermediacy of Indol-3-ylmethyl Isothiocyanates in the Enzymic Hydrolysis of Indole Glucosinolates

The enzymic hydrolysis of 1-methoxyindol-3-ylmethyl glucosinolate (1b) proceeds via the corresponding isothiocyanate (2b), thus providing evidence for a previously unsubstantiated breakdown pathway and establishing a link with 1-methoxycyclobrassinin (4b) and related indole phytoalexins.

IDENTIFICATION OF 1-METHOXYINDOLYL-3-METHYL ISOTHIOCYANATE AS AN INDOLE GLUCOSINOLATE BREAKDOWN PRODUCT

The putative indole glucosinolate enzymic hydrolysis product, 1-methoxyindolyl-3-methyl isothiocyanate has been detected for the first time using low and high resolution mass spectrometry.

SYNTHETIC STUDY FOR 1-METHOXYINDOLES AND 1-METHOXY-2-OXINDOLES

The first syntheses of 1-methoxypimprinine, 9-methoxy-β-carboline derivatives, and 3,3-disubstituted 1-methoxy-2-oxindoles are reported.A practical short step synthetic method for 1-methoxyindole-3-acetonitrile is also reported.