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105748-59-2,MFCD01632490
Catalog No.:AA00851W

105748-59-2 | Brassinin

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1mg
≥98%
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$46.00   $32.00
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5mg
≥98%
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$97.00   $68.00
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10mg
≥98%
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$175.00   $122.00
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25mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00851W
Chemical Name:
Brassinin
CAS Number:
105748-59-2
Molecular Formula:
C11H12N2S2
Molecular Weight:
236.3564
MDL Number:
MFCD01632490
SMILES:
CSC(=S)NCc1c[nH]c2c1cccc2
Properties
Computed Properties
 
Complexity:
233  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
3  
XLogP3:
2.6  

Downstream Synthesis Route

[1]BioorganicandMedicinalChemistry,2006,vol.14,p.4958-4979

[2]NewJournalofChemistry,2018,vol.42,p.13549-13557

[3]JournalofMedicinalChemistry,2006,vol.49,p.684-692

[4]Patent:US2007/105907,2007,A1.Locationinpatent:Page/PagecolumnSheet2/7;7

[5]JournaloftheChemicalSociety.Chemicalcommunications,1986,p.1077-1078

[6]BulletinoftheChemicalSocietyofJapan,1988,vol.61,p.285-290

[1]Tetrahedron,2005,vol.61,p.9257-9262

[2]Heterocycles,1992,vol.33,p.77-80

[3]RSCAdvances,2014,vol.4,p.5575-5582

[1]Tetrahedron,1998,vol.54,p.3549-3566

[2]Tetrahedron,1998,vol.54,p.3549-3566

[3]Synlett,1997,vol.1997,p.289-290

[1]Budovska,Mariana[RSCAdvances,2014,vol.4,#11,p.5575-5582]

[2]Zhong,Xin;Chen,Ning;Xu,Jiaxi[NewJournalofChemistry,2018,vol.42,#16,p.13549-13557]

Literature

Title: Brassinin and its derivatives as potential anticancer agents.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20140801

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans.

Journal: Journal of agricultural and food chemistry 20120815

Title: Differential protein expression in response to the phytoalexin brassinin allows the identification of molecular targets in the phytopathogenic fungus Alternaria brassicicola.

Journal: Molecular plant pathology 20120601

Title: Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells.

Journal: International journal of oncology 20120301

Title: Tumor angiogenesis as a target for dietary cancer prevention.

Journal: Journal of oncology 20120101

Title: Discovery of inhibitors and substrates of brassinin hydrolase: Probing selectivity with dithiocarbamate bioisosteres.

Journal: Bioorganic & medicinal chemistry 20120101

Title: Altered tryptophan metabolism as a paradigm for good and bad aspects of immune privilege in chronic inflammatory diseases.

Journal: Frontiers in immunology 20120101

Title: Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors.

Journal: Bioorganic & medicinal chemistry 20110215

Title: Brassinin oxidase mediated transformation of the phytoalexin brassinin: structure of the elusive co-product, deuterium isotope effect and stereoselectivity.

Journal: Bioorganic & medicinal chemistry 20110215

Title: Detoxification of cruciferous phytoalexins in Botrytis cinerea: spontaneous dimerization of a camalexin metabolite.

Journal: Phytochemistry 20110201

Title: Cell wall integrity and high osmolarity glycerol pathways are required for adaptation of Alternaria brassicicola to cell wall stress caused by brassicaceous indolic phytoalexins.

Journal: Cellular microbiology 20110101

Title: Crinum latifolium leave extracts suppress immune activation cascades in peripheral blood mononuclear cells and proliferation of prostate tumor cells.

Journal: Scientia pharmaceutica 20110101

Title: Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B.

Journal: Organic & biomolecular chemistry 20101121

Title: Cancer prevention with natural compounds.

Journal: Seminars in oncology 20100601

Title: Discovery of inhibitors of brassinin oxidase based on the scaffolds of the phytoalexins brassilexin and wasalexin.

Journal: Bioorganic & medicinal chemistry 20100401

Title: Innate immune responses activated in Arabidopsis roots by microbe-associated molecular patterns.

Journal: The Plant cell 20100301

Title: All mold is not alike: the importance of intraspecific diversity in necrotrophic plant pathogens.

Journal: PLoS pathogens 20100301

Title: Substrate specificity and inhibition of brassinin hydrolases, detoxifying enzymes from the plant pathogens Leptosphaeria maculans and Alternaria brassicicola.

Journal: The FEBS journal 20091201

Title: Plant antimicrobial agents and their effects on plant and human pathogens.

Journal: International journal of molecular sciences 20090801

Title: Trypanosoma cruzi: antiproliferative effect of indole phytoalexins on intracellular amastigotes in vitro.

Journal: Experimental parasitology 20090501

Title: Synthetic inhibitors of the fungal detoxifying enzyme brassinin oxidase based on the phytoalexin camalexin scaffold.

Journal: Journal of agricultural and food chemistry 20090325

Title: Cloning, purification and characterisation of brassinin glucosyltransferase, a phytoalexin-detoxifying enzyme from the plant pathogen Sclerotinia sclerotiorum.

Journal: Fungal genetics and biology : FG & B 20090201

Title: The phytopathogenic fungus Alternaria brassicicola: phytotoxin production and phytoalexin elicitation.

Journal: Phytochemistry 20090201

Title: Brassinin oxidase, a fungal detoxifying enzyme to overcome a plant defense -- purification, characterization and inhibition.

Journal: The FEBS journal 20080701

Title: A key in vivo antitumor mechanism of action of natural product-based brassinins is inhibition of indoleamine 2,3-dioxygenase.

Journal: Oncogene 20080501

Title: Benzyl N-[2-(1H-indol-3-yl)eth-yl]dithio-carbamate.

Journal: Acta crystallographica. Section E, Structure reports online 20080101

Title: Isosteric probes provide structural requirements essential for detoxification of the phytoalexin brassinin by the fungal pathogen Leptosphaeria maculans.

Journal: Bioorganic & medicinal chemistry 20070915

Title: Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum.

Journal: Bioorganic & medicinal chemistry 20070901

Title: Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase.

Journal: Phytochemistry 20070601

Title: Elimination of isocyanate and isothiocyanate molecules at the electrospray ionization ion trap, electrospray ionization quadrupole time-of-flight and matrix-assisted laser desorption/ionization time-of-flight tandem mass spectrometry fragmentation of sodium cationized brassitin, brassinin and their glycosides.

Journal: European journal of mass spectrometry (Chichester, England) 20070101

Title: Isobrassinin and its analogues: novel types of antiproliferative agents.

Journal: Bioorganic & medicinal chemistry letters 20061215

Title: Detection, characterization and identification of crucifer phytoalexins using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.

Journal: Journal of chromatography. A 20061110

Title: Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin.

Journal: Bioorganic & medicinal chemistry 20060715

Title: Structure-activity study of brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors.

Journal: Journal of medicinal chemistry 20060126

Title: Camalexin induces detoxification of the phytoalexin brassinin in the plant pathogen Leptosphaeria maculans.

Journal: Phytochemistry 20051101

Title: Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells.

Journal: Leukemia research 20050401

Title: Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains.

Journal: Bioorganic & medicinal chemistry letters 20050401

Title: Conversion of cDNA differential display results (DDRT-PCR) into quantitative transcription profiles.

Journal: BMC genomics 20050101

Title: Detoxification of the cruciferous phytoalexin brassinin in Sclerotinia sclerotiorum requires an inducible glucosyltransferase.

Journal: Phytochemistry 20041001

Title: Natural inhibitors of carcinogenesis.

Journal: Planta medica 20040801

Title: Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity.

Journal: The Journal of organic chemistry 20040625

Title: Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers.

Journal: Neoplasma 20030101

Title: Tryptophan-derived sulfur-containing phytoalexins--a general overview.

Journal: Advances in experimental medicine and biology 20030101

Title: Discovery of cancer preventive agents from natural products: from plants to prevention.

Journal: Current oncology reports 20021101

Title: Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip.

Journal: Phytochemistry 20020301

Title: Botanicals in cancer chemoprevention.

Journal: Cancer metastasis reviews 20020101

Title: Development of a method for mRNA differential display in filamentous fungi: comparison of mRNA differential display reverse transcription polymerase chain reaction and cDNA amplified fragment length polymorphism in Leptosphaeria maculans.

Journal: Canadian journal of microbiology 20011001

Title: Assembling the biosynthetic puzzle of crucifer metabolites: indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not.

Journal: Chemical communications (Cambridge, England) 20010907

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