camalexin

Base Information

• Chemical Name: camalexin
• CAS No.: 135531-86-1
• Molecular Formula: C11H8N2S
• Molecular Weight: 200.264
• European Community (EC) Number: 808-542-7
• DSSTox Substance ID: DTXSID901032122
• Nikkaji Number: J669.040H
• Wikipedia: Camalexin
• Wikidata: Q19903715
• Metabolomics Workbench ID: 48281
• ChEMBL ID: CHEMBL239716
• Mol file: 135531-86-1.mol

Synonyms:2-(1H-indol-3-yl)thiazole;Camalexin;3-Thiazol-2-yl-1H-indole;

Chemical Property of camalexin

Chemical Property:

• Boiling Point: 424.8±47.0 °C(Predicted)
• PKA: 15.49±0.30(Predicted)
• PSA: 56.92000
• Density: 1.336±0.06 g/cm3(Predicted)
• LogP: 3.29140
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 200.04081944
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

98%,99%, ^*data from raw suppliers

Camalexin ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C3=NC=CS3
• General Description: Camalexin is a phytoalexin with notable antifungal properties, particularly against *Cladosporium* sp., and its activity is influenced by the basicity of the indole nitrogen. Synthesized via Grignard reactions involving indolylmagnesium halides and 2-bromothiazole, camalexin and its analogs, such as 6-methoxycamalexin, exhibit varying levels of antifungal efficacy, with camalexin itself being highly active at low concentrations. Structural modifications, especially to the indole nitrogen, can diminish its antifungal potency.

Technology Process of camalexin

There total 28 articles about camalexin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

ethyl 2-(1H-indol-3-yl)thiazole-3(2H)-carboxylate → camalexin (135531-86-1)

Guidance literature:

With o-tetrachloroquinone; In acetonitrile; at 0 ℃; for 1h; Reagent/catalyst;

DOI:10.1002/jhet.3192

Reference yield: 95.0%

methyl 2-(1H-indol-3-yl)thiazole-3(2H)-carboxylate → camalexin (135531-86-1)

Guidance literature:

With o-tetrachloroquinone; In acetonitrile; at 0 ℃; for 1h; Reagent/catalyst;

DOI:10.1002/jhet.3192

Reference yield: 93.0%

2,2,2-trichloroethyl 2-(1H-indol-3-yl)thiazole-3(2H)-carboxylate → camalexin (135531-86-1)

Guidance literature:

With o-tetrachloroquinone; In acetonitrile; at 0 ℃; for 1h; Reagent/catalyst;

DOI:10.1002/jhet.3192

upstream raw materials:

2-bromo-1,3-thiazole

indole

ethyl acetate

1H-indole-3-carboxamide

Downstream raw materials:

2-formamidophenyl-2'-thiazolylketone

2-aminophenyl-2'-thiazolylketone

Refernces

Synthesis of camalexin and related phytoalexins

10.1016/S0040-4020(01)90973-1

The research focused on the synthesis and antifungal activity testing of camalexin and related phytoalexins, which are naturally occurring compounds produced by plants in response to fungal infections. The purpose of the study was to develop efficient short syntheses of camalexin and related 3-(2-thiazoyl)indoles to facilitate further testing of their antifungal activity. The researchers successfully synthesized camalexin and 6-methoxycamalexin using Grignard reactions involving indolylmagnesium halides and 2-bromothiazole. They also prepared other related compounds, including 5-methoxycamalexin and the oxazole analog. The antifungal activities of these compounds were examined against Cladosporium sp., with results indicating that camalexin and thiabendazole displayed significant antifungal activity at a 1 μg application level, while others showed activity at higher application levels. The study concluded that the basicity of the indole nitrogen may be important for antifungal activity, as compounds with modified nitrogen functionality showed reduced activity. Key chemicals used in the synthesis process included indole, methylmagnesium iodide, 2-bromothiazole, and various other substituted indoles and reagents for the preparation of intermediates and final products.