3414-19-5

Basic information

• Product Name: 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE;5-oxidanyl-1H-indole-3-carbaldehyde
• CAS NO: 3414-19-5
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Mol File: 3414-19-5.mol

Chemical Properties

• Boiling Point: 426.3°C at 760 mmHg
• Flash Point: 211.6°C
• Appearance: /
• Density: 1.439g/cm³
• Vapor Pressure: 7.22E-08mmHg at 25°C
• Refractive Index: 1.784
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE(3414-19-5)
• EPA Substance Registry System: 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE(3414-19-5)

Safety Data

• Hazardous Substances Data: 3414-19-5(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is used as a research chemical for studying its properties and potential applications in various fields, including pharmaceuticals and therapeutics.
Used in Pharmaceutical Applications:
5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is used as a precursor in the synthesis of various biologically active molecules, such as neurotransmitters and hormonal substances, for the development of new drugs and therapies.
Used in Drug Discovery and Development:
5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is used as a valuable tool in drug discovery and development due to its versatility and potential medicinal properties.
Used in Antioxidant and Anti-Inflammatory Applications:
5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is studied for its potential antioxidant and anti-inflammatory properties, which may contribute to the development of therapeutic applications for various diseases and conditions.

InChI:InChI=1/C9H7NO2/c11-5-6-4-10-9-2-1-7(12)3-8(6)9/h1-5,10,12H

Upstream product

• 1953-54-4 indol-5-ol 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity

Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F420 in these strains. Complementation experiments showed that F420-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F420 were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F420-dependent enzyme in mycobacteria.

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase

Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.

Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani

The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5- hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described.

STUDIES ON THE SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 5-(3'-INDOLAL)-2-THIOHYDANTOIN DERIVATIVES AS ALDOSE REDUCTASE ENZYME INHIBITORS

A new series of 5-(3'-indolal)-2-thiohydantoin derivatives was synthesized and tested for the ability to inhibit bovine lens aldose reductase (AR) enzyme.The compounds were prepared by condensation of substituted indole-3-aldehyde derivatives with 2-thiohydantoin.The capacity of inhibiting the semi-purified bovine lens enzyme in vitro was observed for several of the compounds tested.One of them was found to be effective in reducing the enzyme activity compared with a corresponding well-known AR inhibitor.