119752-76-0

Basic information

• Product Name: brassilexin
• Synonyms: brassilexin;8H-1-Thia-2,8-diazacyclopenta[a]indene;8H-Isothiazolo[5,4-b]indole;NHMBEDDKDVIBQD-UHFFFAOYSA-N
• CAS NO: 119752-76-0
• Molecular Formula: C9H6 N2 S
• Molecular Weight: 174.22
• Product Categories: Aromatics, Heterocycles, Sulfur & Selenium Compounds
• Mol File: 119752-76-0.mol

Chemical Properties

• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 173.1°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Refractive Index: 1.817
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly))
• CAS DataBase Reference: brassilexin(CAS DataBase Reference)
• NIST Chemistry Reference: brassilexin(119752-76-0)
• EPA Substance Registry System: brassilexin(119752-76-0)

Safety Data

• Hazardous Substances Data: 119752-76-0(Hazardous Substances Data)

Usage

Uses

Brassilexin is a novel sulphur-containing phytoalexin from Brassica Juncea L.

InChI:InChI=1/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,10H

Upstream product

• 128229-00-5 2,2'-Bis(3-hydroxyiminomethyleneindolyl)sulfide 
• 119910-45-1 2-bromo-1H-indole-3-carbaldehyde 
• 183946-30-7 2-sulfanylindole-3-carboxaldehyde 
• 212390-48-2 2-mercaptoindole-3-carboxaldehyde oxime 
• 848649-67-2 3-(N,N-dimethylamino)methyleneindoline-2-thione 
• 496-30-0 indolin-2-thione 
• 59-48-3 2-oxoindole 
• 68-12-2 N,N-dimethyl-formamide 
• 339306-62-6 3-(amino)methyleneindoline-2-thione 
• 105748-58-1 cyclobrassinin 

Relevant articles and documents

Microwave-assisted novel and efficient one-pot synthesis of fused steroidal and non-steroidal isothiazoles

An efficient microwave promoted one-pot synthesis of steroidal and non-steroidal isothiazole derivatives from corresponding β-bromo-α, β-unsaturated aldehydes has been described using a sodium thiocyanate-urea system. The β-bromo-α,β-unsaturated aldehydes derivatives are efficiently synthesized from corresponding cyclic ketones using Vilsmeir formylation reaction. The synthetic protocol is also applied for the synthesis of antifungal brassilexin.

A convenient synthesis of isothiazolo[5,4-b]indole (brassilexin) via a polyphosphoric acid initiated ring closure

Brassilexin (4), an antifungal compound previously isolated from Brassica juncea L. (Cruciferae), has been synthesized with an overall yield of 11% starting from 3-indolecarbaldehyde (1).

Unprecedented vilsmeier formylation: Expedient syntheses of the cruciferous phytoalexins sinalexin and brassilexin and discovery of a new heteroaromatic ring system

Matrix presented A very concise first synthesis of sinalexin was achieved by regioselective formylation of 1-methoxyindoline-2-thione under Vilsmeier conditions followed by unprecedented ammonia workup. Similar formylation of indoline-2-thione yielded brassilexin and a novel pentacyclic heteroaromatic compound resulting from condensation of the Vilsmeier adduct of indoline-2-thione. Both sinalexin and brassilexin displayed strong antifungal activity against several pathogens of crucifers.

Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation

(Chemical Equation Presented) Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation-amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation-amination, expanding substantially the scope of the Vilsmeier formylation of both indoline-2-thiones and indolin-2-ones. The examination of the formylation-amination reaction and optimization of conditions, as well as the syntheses and antifungal activities of several brassilexin analogues, are reported.

Strategies of cruciferous pathogenic fungi: Detoxification of the phytoalexin cyclobrassinin by mimicry

The remarkable metabolism of the cruciferous phytoalexin cyclobrassinin by the phytopathogenic root rot (Rhizoctonia solani Kuhn) and blackleg [Phoma lingam (Tode ex Fr.) Desm., asexual stage of Leptosphaeria maculans (Desm.) Ces. et de Not.] fungi is reported. It was established that R. solani metabolized and detoxified cyclobrassinin via the phytoalexin brassicanal A, which was further transformed into nontoxic products. Detoxification of cyclobrassinin in P. lingam avirulent isolate unity occurred via the phytoalexin brassilexin, whereas the detoxification in P. lingam virulent isolate BJ 125 occurred via the phytoalexin dioxibrassinin. The chemistry involved in the structure determination of the intermediates of these three apparently different pathways and their antifungal activities are described. In addition, efficient syntheses of both phytoalexins brassicanal A and brassilexin by mimicry of the fungal biotransformation route are reported. Implications of these unprecedented transformations are discussed.

A convenient synthesis of the cruciferous phytoalexins brassicanal A and brassilexin by mimicry of a fungal detoxification pathway

The cruciferous phytoalexin brassilexin 3 has been synthesized in four steps from indoline-2-thione via 3-(aminomethylene)indole-2-thione 2, a metabolic intermediate of the detoxification pathway of the phytoalexin cyclobrassinin 1; in addition, the phytoalexin brassicanal A 8 has been synthesized in two steps from 2-indolinethione.

Strategies of fungal pathogens: detoxification of a cruciferous phytoalexin by mimicry

Two different isolates of the phytopathogen Phoma lingam metabolized and phytoalexin cyclobrassinin 3 to the phytoalexins dioxibrassinin 5 and brassilexin 9; both 5 and 9 were further metabolised and detoxified by each fungal isolate.

Oxidative Ring Contraction of the Phytoalexin Cyclobrassinin: a Way to Brassilexin

Periodate-induced degradation of cyclobrassinin gives brassilexin in 30percent yield.