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
• Article Data: 5

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

General Description

5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is a chemical compound that belongs to the class of indole derivatives. It is a yellow-brown solid that is commonly used in research and pharmaceutical applications. 5-HYDROXY-1H-INDOLE-3-CARBALDEHYDE is an aldehyde derivative of 5-hydroxyindole and is often utilized as a precursor in the synthesis of various biologically active molecules, including neurotransmitters and hormonal substances. Its versatility and potential medicinal properties make it a valuable tool in drug discovery and development. Additionally, it has also been studied for its potential antioxidant and anti-inflammatory properties, highlighting its potential therapeutic applications.

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.

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.

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.