23158-16-9

Basic information

• Product Name: 6-Prenyl-1H-indole
• Synonyms: 6-(3-Methyl-2-butenyl)-1H-indole;6-Prenyl-1H-indole;6-Prenylindole;Antibiotic 434B
• CAS NO: 23158-16-9
• Molecular Formula: C13H15N
• Molecular Weight: 0
• Mol File: 23158-16-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Prenyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Prenyl-1H-indole(23158-16-9)
• EPA Substance Registry System: 6-Prenyl-1H-indole(23158-16-9)

Safety Data

• Hazardous Substances Data: 23158-16-9(Hazardous Substances Data)

Usage

Description

6-Prenylindole is a bacterial metabolite that has been found in Streptomyces and has antifungal and antimalarial properties. It is active against A. brassicicola strain TP-F0423 and F. oxysporum f. sp. tulipae TU-4-2 (15 and 30 μg/disc in the paper disc assay), and also drug-resistant P. falciparum strain K1 (IC50 = 21 μg/ml).

Uses

6-?(3-?Methyl-?2-?buten-?1-?yl)?-?1H-?indole is an antifungal metabolite isolated from Streptomyces. It can also be found in oil of the roots of M. tenuifolia.

Upstream product

• 513-35-9 2-methyl-but-2-ene 
• 1309684-56-7 6-(3,3-dimethylallyl)tryptophan 
• 147621-18-9 6-indolylboronic acid 
• 870-63-3 prenyl bromide 
• 1026346-82-6 4-(1-benzenesulfonyl-1H-indol-6-yl)-2-methyl-but-3-en-2-ol 
• 679794-03-7 1‐(benzenesulfonyl)‐6‐bromo‐1H‐indole 
• 52415-29-9 6-bromo-1H-indole 
• 124186-73-8 2-[4-Methyl-1-((E)-3-oxo-propenyl)-pent-3-enyl]-pyrrole-1-carboxylic acid methyl ester 

Downstream Products

• 102275-63-8 3,6-Bis-(3,3-dimethylallyl)-1-tosylindol 
• 102275-64-9 3,6-Di-(2,3-epoxy-3-methylbutyl)-1-tosylindol 
• 55045-00-6 2-(2-methylbut-3-en-2-yl)-6-(3-methylbut-2-en-1-yl)-1H-indole 

Relevant articles and documents

Synthesis of 2,6,7-Trisubstituted Prenylated indole

Prenylated indole alkaloids bearing more than one prenyl or reverse-prenyl group show various biological activities. Among them, synthesis of trisubstituted-type prenylated indoles have not been well explored because of the difficulty in regioselective introduction of multiple prenyl and reverse-prenyl groups due to steric hindrance problems. Herein, we describe a synthesis of 2,6,7-trisubstituted prenylated indole using aza-Claisen rearrangement under mild conditions to introduce a prenyl group at C7 in the presence of the prenyl group at C6.

Identification of 6-prenylindole as an antifungal metabolite of Streptomyces sp. TP-A0595 and synthesis and bioactivity of 6-substituted indoles

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Constituents of tropical medicinal plants, XXII: Total syntheses in the hexalobine series

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