351015-67-3

Basic information

• Product Name: 1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE
• CAS NO: 351015-67-3
• Molecular Formula: C12H13NO2
• Molecular Weight: 203.24
• Mol File: 351015-67-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE(351015-67-3)
• EPA Substance Registry System: 1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE(351015-67-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 351015-67-3(Hazardous Substances Data)

Usage

Structure

A derivative of indole, a heterocyclic aromatic compound with a bicyclic structure

Functional groups

Contains a hydroxyl group, a propyl chain, and an aldehyde functional group at the 3 position of the ring

Potential applications

Pharmaceutical industry, organic synthesis, and chemical research

Use

Building block for the synthesis of various bioactive molecules and as a starting material for the production of pharmaceutical intermediates

Ongoing research

Further exploration of its properties and potential applications is in progress

Upstream product

• 56276-06-3 3-(1H-indol-1-yl)propan-1-ol 
• 6639-06-1 3-indol-1-yl-propionic acid 
• 125314-98-9 N-(3-acetoxypropyl)-indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 111480-86-5 1-Allyl-1H-indole-3-carboxaldehyde 
• 120-72-9 indole 
• 627-30-5 1-chloro-3-hydroxypropane 
• 627-18-9 1-bromo-3-propanol 

Relevant articles and documents

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N-(Hydroxyalkyl) derivatives of tris(1H-indol-3-yl)methylium salts as promising antibacterial agents: Synthesis and biological evaluation

The wide spread of pathogens resistance requires the development of new antimicrobial agents capable of overcoming drug resistance. The main objective of the study is to elucidate the effect of substitutions in tris(1H-indol-3-yl)methylium derivatives on their antibacterial activity and toxicity to human cells. A series of new compounds were synthesized and tested. Their antibacterial activity in vitro was performed on 12 bacterial strains, including drug resistant strains, that were clinical isolates or collection strains. The cytotoxic effect of the compounds was determined using an test with HPF-hTERT (human postnatal fibroblasts, immortalized with hTERT) cells. The activity of the obtained compounds depended on the carbon chain length. Derivatives with C5–C6 chains were more active. The minimum inhibitory concentration (MIC) of the most active compound on Gram-positive bacteria, including MRSA, was 0.5 μg/mL. Compounds with C5–C6 chains also revealed high activity against Staphylococcus epidermidis (1.0 and 0.5 μg/mL, respectively) and moderate activity against Gram-negative bacteria Escherichia coli (8 μg/mL) and Klebsiella pneumonia (2 and 8 μg/mL, respectively). However, they have no activity against Salmonella cholerasuis and Pseudomonas aeruginosa. The most active compounds revealed higher antibacterial activity on MRSA than the reference drug levofloxacin, and their ratio between antibacterial and cytotoxic activity exceeded 10 times. The data obtained provide a basis for further study of this promising group of substances.

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A compound has Formula I: A, B, C, D, W, X, Y, and Z are independently selected from hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C1-C6 alkoxy, aryl, aldehyde, protected aldehyde, CH, N, O, S, null, and bond; Q is selected from aldehyde, protected aldehyde, and null, at least one of A, B, C, D, W, X, Y, Z, or Q is an aldehyde or protected aldehyde; the bonds between each of A-B, B-C, C-D, W-X, X-Y, and Y-Z are selected from single bond, double bond, triple bond, and no bond; L is a linker selected from a C1-C12 alkyl, aralkyl, and aryl, any of which is optionally substituted; one or more methylene unit (CH2) of the C1-C12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH; and R1 and R2 are independently selected from —NR3R4, halogen, C1-C8 alkoxy, aralkoxy, alkenyloxy, alkynyloxy, and OCH2CH2CN; R3 and R4 are independently a C1-C4, straight chain or branched alkyl group.

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