1204-06-4

Usage

Uses

Used in Molecular Biology and Genetic Engineering:
3-Indoleacrylic acid is used as an inducer for the expression of ribokinase in E. coli. This application is crucial in the field of molecular biology and genetic engineering, as it allows for the manipulation and study of gene expression in bacterial systems. By inducing the expression of specific genes, researchers can gain valuable insights into the functions and interactions of various genetic elements.
Used in Pharmaceutical Research:
As a chemical inducer, 3-Indoleacrylic acid can also be employed in the development of novel pharmaceutical compounds. By understanding how 3-Indoleacrylic acid interacts with specific genes and proteins, researchers can potentially design new drugs that target these genetic elements, leading to the development of more effective treatments for various diseases and conditions.
Used in Biotechnology:
In the field of biotechnology, 3-Indoleacrylic acid can be utilized for the production of recombinant proteins. By inducing the expression of specific genes, biotechnologists can produce large quantities of proteins with desired characteristics, which can then be used for various applications, such as the development of new drugs, vaccines, or diagnostic tools.
Used in Research and Development:
3-Indoleacrylic acid is also valuable in research and development settings, where it can be used to study the mechanisms of gene regulation and expression. This knowledge can be applied to develop new strategies for gene therapy, as well as to improve our understanding of the underlying causes of various genetic disorders.

Synthesis Reference(s)

Synthesis, p. 236, 1984 DOI: 10.1055/s-1984-30787

Biochem/physiol Actions

3-Indoleacrylic acid helps to block the mycelial growth of?Neurospora crassa. As a result, the cells accumulate indoleglycerol phosphate, which influences the rate of tryptophan synthetase.

Purification Methods

Recrystallise the acid from AcOH, H2O or EtOAc/cyclohexane. UV in MeOH has at 225, 274 and 325nm. [Shaw et al. J Org Chem 23 1171 1958, constitution: Rappe Acta max Chem Scand 18 818 1964, Moffatt J Chem Soc 1442 1957, Kimming et al. Hoppe Seyler's Z Physiol Chem 371 234 1958, Beilstein 22 V 249.]

InChI:InChI=1/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 141-82-2 malonic acid 
• 22948-94-3 1-acetyl-3-indolylcarbaldehyde 
• 830-96-6 Indole-3-propionic acid 
• 87894-44-8 (E)-3-(1-Acetyl-1H-indol-3-yl)-acrylic acid ethyl ester 
• 576-15-8 N-acetylindole 
• 110110-44-6 cis-3-(β-carbethoxyvinyl)indole 
• 19626-93-8 (E)-methyl 3-(1-acetyl-1H-indol-3-yl)acrylate 
• 110110-37-7 3-(1H-indol-3-yl)-acrylic acid ethyl ester 

Downstream Products

• 120681-20-1 (E)-3-(1H-Indol-3-yl)-acryloyl chloride 
• 359700-09-7 (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid 
• 29953-72-8 cis-3-indole acrylic acid 
• 1422432-44-7 C₁₇H₁₄N₂O 
• 1422432-46-9 C₂₁H₂₀N₂O₃ 
• 1422432-52-7 C₁₉H₁₆N₂O₃ 
• 1610703-50-8 (E)-N-(3,5-dimethoxyphenyl)-3-(1H-indol-3-yl)acrylamide 
• 1610703-51-9 (E)-3-(1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl)acrylamide 
• 1610703-52-0 (E)-3-(1H-Indol-3-yl)-N-(2,4,6-trimethoxyphenyl)acrylamide 
• 1610703-53-1 (E)-N-(4-hydroxy-3-methoxybenzyl)-3-(1H-indol-3-yl)acrylamide 
• 1610703-54-2 (E)-N-(2,3-dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 
• 1610703-55-3 (E)-N-(2,4-dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 
• 1610703-56-4 (E)-N-(2,5-dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 
• 1610703-47-3 (E)-N-(2,4-dimethoxyphenyl)-3-(1H-indol-3-yl)acrylamide 

Relevant academic research and scientific papers

Spermine Derivatives of Indole-3-carboxylic Acid, Indole-3-acetic Acid and Indole-3-acrylic Acid as Gram-Negative Antibiotic Adjuvants

The discovery of new antibiotic adjuvants is an attractive option for overcoming antimicrobial resistance. We have previously reported the discovery of a bis-6-bromoindolglyoxylamide derivative of spermine as being able to enhance the action of antibiotics against Gram-negative bacteria but suffers from being cytotoxic and red-blood cell haemolytic. A series of analogues was prepared exploring variation of the indolglyoxylamide unit, to include indole-3-acrylic, indole-3-acetic and indole-3-carboxylate units, and evaluated for antibiotic enhancing properties against a range of Gram-negative bacteria, and for intrinsic antimicrobial, cytotoxic and haemolytic properties. Two spermine derivatives, bearing 5-bromo-indole-3-acetic acid (17) and 5-methoxy-indole-3-acrylic acid (14) end groups were found to exhibit good to moderate antibiotic adjuvant activities for doxycycline towards the Gram-negative bacteria Pseudomonas aeruginosa, Escherichia coli and Klebsiella pneumoniae, but with more modest intrinsic antimicrobial activity and greatly reduced cytotoxic and haemolytic properties. The mechanism of action of the latter derivative identified its ability to disrupt the outer membranes of bacteria and to inhibit the AcrAB-TolC efflux pump directly or by inhibiting the proton gradient.

Induction of Apoptosis in Hepatocellular Carcinoma Cell Lines by Novel Indolylacrylamide Derivatives: Synthesis and Biological Evaluation

Hepatocellular carcinoma (HCC) is the most prevalent primary liver cancer and one of the leading causes of cancer associated death worldwide. This is due to the highly resistant nature of this malignancy and the lack of effective treatment options for advanced stage HCC patients. The hyperactivity of PI3K/Akt and Ras/Raf/MEK/ERK signaling pathways contribute to the cancer progression, survival, motility, and resistance mechanisms, and the interaction of these two pathways are responsible for the regulation of cancer cell growth and development. Therefore, it is vital to design and develop novel therapeutic options for HCC treatment targeting these hyperactive pathways. For this purpose, novel series of trans-indole-3-ylacrylamide derivatives originated from the lead compound, 3-(1H-indole-3-yl)-N-(3,4,5-trimethoxyphenyl)acrylamide, have been synthesized and analyzed for their bioactivity on cancer cells along with the lead compound. Based on the initial screening, the most potent compounds were selected to elucidate their effects on cellular signaling activity of HCC cell lines. Cell cycle analysis, immunofluorescence, and Western blot analysis revealed that lead compound and (E)-N-(4-tert-butylphenyl)-3-(1H-indole-3-yl)acrylamide induced cell cycle arrest at the G2/M phase, enhanced chromatin condensation and PARP-cleavage, addressing induction of apoptotic cell death. Additionally, these compounds decreased the activity of ERK signaling pathway, where phosphorylated ERK1/2 and c-Jun protein levels diminished significantly. Relevant to these findings, the lead compound was able to inhibit tubulin polymerization as well. To conclude, the novel trans-indole-3-ylacrylamide derivatives inhibit one of the critical pathways associated with HCC which results in cell cycle arrest and apoptosis in HCC cell lines.

Synthesis, biological evaluation and molecular docking studies of trans-indole-3-acrylamide derivatives, a new class of tubulin polymerization inhibitors

In this study, we synthesized a series of trans-indole-3-acrylamide derivatives (3a-k) and investigated their activity for inhibition of cell proliferation against five human cancer cell lines (HeLa, MCF7, MDA-MB-231, Raji and HL-60) by MTT assay. Compound 3e showed significant antiproliferative activity against both the Raji and HL-60 cell lines with IC50 values of 9.5 and 5.1 μM, respectively. Compound 3e also exhibited moderate inhibitory activity on tubulin polymerization (IC50 = 17 μM). Flow cytometric analysis of cultured cells treated with 3e also demonstrated that the compound caused cell cycle arrest at the G2/M phase in HL-60 and HeLa cells. Moreover, 3e, the most active compound, caused an apoptotic cell death through the activation of caspase-3. Docking simulations suggested that 3e binds to the colchicine site of tubulin.

L-Tryptophan 2',3'-oxidase from Chromobacterium violaceum catalyzes the synthesis of &α,&β-dehydrotryptophanyl residues in peptides and proteins: A tool for chemical modification and labelling of peptides and proteins

In 1975, Davis et al. reported the capacity of Chromobacterium violaceum (ATCC 12472) to transform Cbz-L-tryptophan into its α,β-dehydro derivative.However, reaction specificity and structural features of the putative enzyme which is responsible for this activity were not determined.We have isolated from this strain an enzyme designated L-tryptophan 2',3'-oxidase, which catalyzes the formation of a double bond at the Cα-Cβ position of tryptophan residues.Using a variety of tryptophan derivatives, we have demonstrated thatthe enzyme is highly specific for unsubstituted indole containing compounds and showed that the enzyme not only acts on isolated tryptophanyl side-chains but is also capable of dehydrogenating tryptophan residues in peptides and proteins.

Synthesis of Enamides

(Z)-3-Arylprop-2-enoic acids can be converted by the Curtius procedure, through the acyl azides, into (Z)-2-arylethenyl isocyanates, which with methanol give methyl (Z)-N-(2-arylethenyl)carbamates.Acylation of the (Z)-enecarbamates, through their anions, leads to methyl (Z)-N-acyl-N-(2-arylethenyl)carbamates, which on treatment with lithium iodide in boiling N,N-dimethylformamide or acetonitrile undergo demethoxycarbonylation to give (Z)-enamides.The stereospecific route to enamides can also be used in the E-series.Treatment of (Z)- or (E)-2-arylethenyl isocyanates with trifluoroacetic acid gives (E)-N-(2-arylethenyl)trifluoroacetamides,the anions of which, with acylating agents, give (E)-enamides directly.

Alkenylation of 1-Acylindoles with Olefins Bearing Electron-withdrawing Substituents and Palladium Acetate

The oxidation of 1-(2,6-dichlorobenzoyl)indole with olefins, such as alkyl acrylates and acrylonitrile, and palladium acetate resulted in selective 3-alkenylation of the indole nucleus.Treatment of 1-acyl-3-methylindoles under similar conditions gave the corresponding 2-alkenyl substituted indoles, while the oxidation of 6-oxo-6H-isoindoloindole gave the corresponding 3-alkenyl substituted indoles.