135531-86-1

Basic information

• Product Name: camalexin
• Synonyms: camalexin;3-(Thiazol-2-yl)-1H-indole;Camalexine
• CAS NO: 135531-86-1
• Molecular Formula: C₁₁H₈N₂S
• Molecular Weight: 200.25962
• Mol File: 135531-86-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 424.8±47.0 °C(Predicted)
• Appearance: white to light brown/
• Density: 1.336±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble20mg/mL, clear
• PKA: 15.49±0.30(Predicted)
• CAS DataBase Reference: camalexin(CAS DataBase Reference)
• NIST Chemistry Reference: camalexin(135531-86-1)
• EPA Substance Registry System: camalexin(135531-86-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-45
• WGK Germany: 3
• Hazardous Substances Data: 135531-86-1(Hazardous Substances Data)

Usage

Description

Camalexin is an alkaloid released by plants of the Brassicaceae family in response to pathogen infection. In addition to antimicrobial properties and a role in plant defense, camalexin exhibits antiproliferative activity in vitro against various cancer cell lines. Camalexin is active against HeLa, Jurkat, MDA-MB-231, and CEM cancer cell lines (IC50s = 50.0, 46.2, 77.7, and 67.6 μM, respectively), but it is also toxic to primary human umbilical vein endothelial cells (HUVEC; (IC50 = 74.0 μM). Camalexin induces apoptosis in Jurkat cells by increasing reactive oxygen species (ROS) levels and activating caspase-8 and caspase-9. In human prostate cancer cell lines, camalexin (25 μM) is more active against aggressive lines and increases ROS levels and apoptosis via cathepsin D relocation from lysosomes to the cytosol.

Uses

Camalexin has been used in quantification and tolerance assays in Arabidopsis thaliana leaves.

Definition

ChEBI: An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.

Synthesis Reference(s)

Tetrahedron, 51, p. 773, 1995 DOI: 10.1016/0040-4020(94)00987-6

Biochem/physiol Actions

Camalexin is a phytoalexin isolated from cruciferous plants that exhibits antibacterial, antifungal, antiproliferative and cancer chemopreventive activities. Apparently, camalexin increases the ROS levels and is more effective in aggressive prostate cancer cells that express high ROS levels. In Arabidopsis thaliana, camalexin and salicylic acid confer resistance to Phytophthora capsici.

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 120-72-9 indole 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 59108-90-6 1H-indole-3-carbothioamide 
• 192189-07-4 tert-butyl 3-iodo-1H-indol-1-carboxylate 
• 942070-45-3 tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 
• 39254-87-0 2-aminophenyl-2'-thiazolylketone 
• 610-14-0 2-nitrobenzyl chloride 
• 552-89-6 2-nitro-benzaldehyde 
• 39264-15-8 (2-nitrophenyl)-(2-thiazolyl)methanol 
• 39264-16-9 2-nitrophenyl-2'-thiazolylketone 
• 80360-14-1 3-iodo-1-phenylsulfonyl-1H-indole 
• 26340-47-6 3-Iodo-1H-indole 
• 204764-05-6 1-(tert-butoxycarbonyl)-4-methoxycarbonyl-3-(thiazolidin-2-yl)indole 

Downstream Products

• 161988-57-4 2-formamidophenyl-2'-thiazolylketone 
• 39254-87-0 2-aminophenyl-2'-thiazolylketone 

Related news

De novo genetic engineering of the camalexin (cas 135531-86-1) biosynthetic pathway08/14/2019

Camalexin is a tryptophan-derived phytoalexin that is induced in the model plant Arabidopsis thaliana upon pathogen attack. Only few genes in the biosynthetic pathway of camalexin remain unidentified, however, investigation of candidate genes for these steps has proven particularly difficult par...detailed

Metal hyperaccumulation in the Brassicaceae species Arabidopsis halleri reduces camalexin (cas 135531-86-1) induction after fungal pathogen attack08/13/2019

Metal hyperaccumulation from the soil by certain plant species can serve as a defence trait. Such hyperaccumulation might impact the expression of organic defences. Here, the induction of the phytoalexin camalexin after leaf infection with a pathogenic fungus was investigated in plants of the fa...detailed

Relevant articles and documents

Synthesis of (3-indolyl)heteroaromatics by Suzuki-Miyaura coupling and their inhibitory activity in lipid peroxidation

A variety of (3-indolyl)heteroaromatic compounds were synthesized by Suzuki-Miyaura coupling of 3-indolylboronic acid and halogenated heteroaromatics. 2-(3-Indolyl)thiophene showed potent inhibitory activity against lipid peroxidation by rat liver microsome.

Synthesis of camalexin

In this paper we describe a new method for the synthesis of camalexin (1) based on the reaction of 1-(tert-butoxycarbonyl)indole-3-carboxaldehyde with methyl L-cysteinate hydrochloride, followed by oxidation and decarboxylation. Compounds 1, and intermediates 5-7 were identified by elemental analysis, 1H NMR, 13C NMR and mass spectroscopy.

Synthesis of Camalexin and Related Analogues

Camalexin is synthesized on a gram scale by coupling of thiazole and indole in an amidoalkylation–oxidation sequence. Several high-yielding implementations of this two-step approach are demonstrated with variation of either the intermediate acyliminium reagent or the oxidation conditions. Benzo-analogues and aza-analogues of the natural product are also obtained by this method. As a side result, a new formylation of indole is demonstrated.