Brassilexin

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H563316

CAS#: 119752-76-0

Description: Brassilexin is an inhibitor of cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola.


Chemical Structure

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Brassilexin
CAS# 119752-76-0

Theoretical Analysis

Hodoodo Cat#: H563316
Name: Brassilexin
CAS#: 119752-76-0
Chemical Formula: C9H6N2S
Exact Mass: 174.03
Molecular Weight: 174.220
Elemental Analysis: C, 62.05; H, 3.47; N, 16.08; S, 18.40

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Brassilexin; Brassilexine;

IUPAC/Chemical Name: 2H-[1,2]Thiazolo[5,4-b]indole

InChi Key: YPQKRKAUPLJHDT-UHFFFAOYSA-N

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

SMILES Code: C12=NC3=C(C=CC=C3)C1=CNS2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 174.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pedras MS, Minic Z. The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola. Bioorg Med Chem. 2014 Jan 1;22(1):459-67. doi: 10.1016/j.bmc.2013.11.005. Epub 2013 Nov 13. PubMed PMID: 24275350.

2: Pedras MS, Hossain S, Snitynsky RB. Detoxification of cruciferous phytoalexins in Botrytis cinerea: spontaneous dimerization of a camalexin metabolite. Phytochemistry. 2011 Feb;72(2-3):199-206. doi: 10.1016/j.phytochem.2010.11.018. Epub 2010 Dec 20. PubMed PMID: 21176925.

3: Pedras MS, Snitynsky RB. Impact of cruciferous phytoalexins on the detoxification of brassilexin by the blackleg fungus pathogenic to brown mustard. Nat Prod Commun. 2010 Jun;5(6):883-8. PubMed PMID: 20614815.

4: Pedras MS, Minic Z, Sarma-Mamillapalle VK, Suchy M. Discovery of inhibitors of brassinin oxidase based on the scaffolds of the phytoalexins brassilexin and wasalexin. Bioorg Med Chem. 2010 Apr 1;18(7):2456-63. doi: 10.1016/j.bmc.2010.02.054. Epub 2010 Mar 2. PubMed PMID: 20303277.

5: Sexton AC, Minic Z, Cozijnsen AJ, Pedras MS, Howlett BJ. Cloning, purification and characterisation of brassinin glucosyltransferase, a phytoalexin-detoxifying enzyme from the plant pathogen Sclerotinia sclerotiorum. Fungal Genet Biol. 2009 Feb;46(2):201-9. doi: 10.1016/j.fgb.2008.10.014. Epub 2008 Nov 13. PubMed PMID: 19041410.

6: Pedras MS, Zheng QA, Gadagi RS, Rimmer SR. Phytoalexins and polar metabolites from the oilseeds canola and rapeseed: differential metabolic responses to the biotroph Albugo candida and to abiotic stress. Phytochemistry. 2008 Feb;69(4):894-910. Epub 2007 Nov 26. PubMed PMID: 18039546.

7: Pedras MS, Hossain M. Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation. Org Biomol Chem. 2006 Jul 7;4(13):2581-90. Epub 2006 May 30. PubMed PMID: 16791322.

8: Pedras MS, Suchy M. Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans. Bioorg Med Chem. 2006 Feb 1;14(3):714-23. Epub 2005 Oct 3. PubMed PMID: 16202609.

9: Pedras MS, Suchy M. Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid. Org Biomol Chem. 2005 May 21;3(10):2002-7. Epub 2005 Apr 22. PubMed PMID: 15889184.

10: Pedras MS, Jha M. Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation. J Org Chem. 2005 Mar 4;70(5):1828-34. PubMed PMID: 15730307.

11: Pedras MS, Montaut S, Suchy M. Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity. J Org Chem. 2004 Jun 25;69(13):4471-6. PubMed PMID: 15202903.

12: Miedzybrodzki R. [Biological activity of the isothiazole derivatives]. Postepy Hig Med Dosw. 2003;57(6):617-30. Review. Polish. PubMed PMID: 15002160.

13: Mezencev R, Mojzis J, Pilatova M, Kutschy P. Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers. Neoplasma. 2003;50(4):239-45. Review. PubMed PMID: 12937834.

14: Pedras MS, Nycholat CM, Montaut S, Xu Y, Khan AQ. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry. 2002 Mar;59(6):611-25. PubMed PMID: 11867093.

15: Pedras MS, Zaharia IL. Unprecedented Vilsmeier formylation: expedient syntheses of the cruciferous phytoalexins sinalexin and brassilexin and discovery of a new heteroaromatic ring system. Org Lett. 2001 Apr 19;3(8):1213-6. PubMed PMID: 11348197.

16: Pedras MS, Okanga FI. Strategies of cruciferous pathogenic fungi: detoxification of the phytoalexin cyclobrassinin by mimicry. J Agric Food Chem. 1999 Mar;47(3):1196-202. PubMed PMID: 10552437.

17: Pedras MS, Loukaci A, Okanga FI. The cruciferous phytoalexins brassinin and cyclobrassinin are intermediates in the biosynthesis of brassilexin. Bioorg Med Chem Lett. 1998 Nov 3;8(21):3037-8. PubMed PMID: 9873671.

18: Tempête C, Devys M, Barbier M. Growth inhibitions on human cancer cell cultures with the indole sulphur-containing phytoalexins and their analogues. Z Naturforsch C. 1991 Jul-Aug;46(7-8):706-7. PubMed PMID: 1777001.

19: Rouxel T, Kollmann A, Boulidard L, Mithen R. Abiotic elicitation of indole phytoalexins and resistance to Leptosphaeria maculans within Brassiceae. Planta. 1991 May;184(2):271-8. doi: 10.1007/BF00197957. PubMed PMID: 24194080.