88210-96-2

Basic information

• Product Name: 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID
• Synonyms: 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLIC ACID;5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID;AKOS JY2083042;5,6-dimethoyxindole-2-carboxylic acid;1H-Indole-2-carboxylic acid, 5,6-dimethoxy-;5,6-Dica;5,6-Dimethoxyindolyl-2-carboxylic acid
• CAS NO: 88210-96-2
• Molecular Formula: C₁₁H₁₁NO₄
• Molecular Weight: 221.21
• Mol File: 88210-96-2.mol

Chemical Properties

• Melting Point: 210°C (dec.)
• Boiling Point: 456.2°C at 760 mmHg
• Flash Point: 229.7°C
• Appearance: /
• Density: 1.362g/cm³
• Vapor Pressure: 4.08E-09mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: 2-8°C
• PKA: 4.48±0.30(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 202249
• CAS DataBase Reference: 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID(88210-96-2)
• EPA Substance Registry System: 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID(88210-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 88210-96-2(Hazardous Substances Data)

Usage

Uses

Used in Synthetic Chemistry:
5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID is used as a reagent and heterocyclic building block in synthetic chemistry for the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows for versatile chemical reactions and modifications, making it a valuable component in the development of new molecules with potential applications in various fields.
Used in Electrochromic Applications:
5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID is used as a precursor to prepare a melanin-like polymer, poly(5,6-dimethoxyindole-2-carboxylic acid), which exhibits electrochromic properties. This polymer can change its color and optical properties in response to an applied electric field, making it suitable for applications in smart windows, displays, and other optoelectronic devices.
Used in Pharmaceutical Industry:
5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID can be used as a starting material for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Research and Development:
5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID is also used in research and development for studying the properties and behavior of melanin-like polymers and other related compounds. This can help scientists gain a better understanding of their potential applications and optimize their synthesis and performance.

InChI:InChI=1/C11H11NO4/c1-15-9-4-6-3-8(11(13)14)12-7(6)5-10(9)16-2/h3-5,12H,1-2H3,(H,13,14)

Upstream product

• 60-18-4 L-tyrosine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 911301-33-2 (E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 690639-23-7 methyl 2-azido-3-(3',4'-dimethoxyphenyl)-propenoate 
• 157670-07-0 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 
• 28059-24-7 methyl 5,6-dimethoxy-1H-indole-2-carboxylate 
• 16382-18-6 5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester 

Downstream Products

• 690639-24-8 5,6-dimethoxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 
• 874797-21-4 5,6-dimethoxy-3-(3,4,5-trimethoxy-phenylthio)-1H-indole-2-carboxylic acid methyl ester 
• 1263787-90-1 C₁₉H₁₉IN₂O₃ 
• 14430-23-0 5,6-dimethoxyindole 
• 812653-13-7 18-[5,6-dimethoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 812653-12-6 16-[5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]hexadecan-1-ol 
• 812652-87-2 5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 142769-27-5 5,6-dimethoxy-1H-indole-3-carbaldehyde 
• 690639-25-9 5,6-dihydroxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 
• 32045-07-1 methyl 5,6-dimethoxy-1-methyl-1H-indole-2-carboxylate 
• 380607-13-6 5,6-dimethoxy-1-methyl-1H-indole-2-carboxylic acid 

Relevant articles and documents

Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.

Synthesis and agonistic activity at the GPR35 of 5,6-dihydroxyindole-2- carboxylic acid analogues

5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free dynamic mass redistribution and Tango β-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs

A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5-7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3- (chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3- dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5-7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.

Hyperbranched molecular structures with potential antiviral activity: Derivatives of 5,6-dihydroxyindole-2-carboxylic acid

In the search of new HIV-1 integrase (IN) inhibitors, we synthesized a series of multimeric 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives. Preliminary results indicate that hyperbranched architectures could represent a peculiar molecular requi

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.

Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres

In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared, 13c (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

The design, synthesis and activity of non-ATP competitive inhibitors of pp60(c-src) tyrosine kinase. Part 2: Hydroxyindole derivatives

As part of continuing effort to identify novel scaffolds that inhibit the pp60(c-src) protein tyrosine kinase, a series of hydroxyindole amides was rationally designed and synthesized. The most potent derivative was found to bind non-competitively with respect to ATP. (C) 2000 Elsevier Science Ltd. All rights reserved.

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.