690639-23-7

Usage

Chemical compound

2-Propenoic acid, 2-azido-3-(3,4-dimethoxyphenyl)-, methyl ester

Also known as

Azidomethyl ester of ferulic acid

Derivative of ferulic acid

A common component of plant cell walls and an antioxidant with potential health benefits

Azido group

Makes it useful for bioconjugation applications

Methyl ester form

Allows for better solubility and stability in organic solvents

Versatile compound

Suitable for various research and industrial purposes in chemical and biological applications

Upstream product

• 1816-92-8 Methyl azidoacetate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 54814-41-4 (+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 
• 54814-41-4 3-(3,4-dimethoxy-phenyl)-2-hydroxy-propionic acid methyl ester 
• 153381-08-9 Methyl (S)-(+)-3-(3,4 dimethoxyphenyl)-2-hydroxypropionate 
• 28059-24-7 methyl 5,6-dimethoxy-1H-indole-2-carboxylate 
• 157670-11-6 (R)-6,7-Dimethoxy-1-methyl-2-((S)-1-phenyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 157670-09-2 2-(5,6-Dimethoxy-1H-indol-3-yl)-2-oxo-N-((S)-1-phenyl-ethyl)-acetamide 
• 157670-10-5 [2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 14430-23-0 5,6-dimethoxyindole 
• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of symmetrical and unsymmetrical diindolylmethanes via acid-catalysed electrophilic substitution reactions

A range of activated indole-2-carboxylate derivatives was prepared via the Hemetsberger indole synthesis. Vilsmeier formylation was explored to establish regioselectivity and to prepare a range of new indole carbaldehydes. The indole aldehydes were reduce

CBI analogues of the duocarmycins and CC-1065

An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50=2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp2, sp3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

The synthesis of roeharmine and (-)-1,2,3,4-tetrahydroroeharmine

The total synthesis of roeharmine 1 as well as an enantiospecific synthesis of (-)-1,2,3,4-tetrahydroroeharmine 2 has been achieved via the Pictet-Spengler reaction as a key step. The optical rotation of synthetic (- )-2 was found to be higher than that reported for the natural product. A possible mechanism for the racemization of 2 upon exposure to acid has been proposed and serves as a warning to alkaloid chemists who isolate ring-A alkoxylated indole alkaloids under acidic conditions.