143005-79-2

Basic information

• Product Name: (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine
• Synonyms: (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine
• CAS NO: 143005-79-2
• Molecular Weight: 179.016
• Mol File: 143005-79-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine(143005-79-2)
• EPA Substance Registry System: (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine(143005-79-2)

Safety Data

• Hazardous Substances Data: 143005-79-2(Hazardous Substances Data)

Upstream product

• 115328-81-9 (S,R)-3-bromo-5-aminomethyl-4,5-dihydroisoxazole 
• 1576241-60-5 C₄H₅BrN₄O 
• 74213-24-4 N-dibromomethylidenehydroxylamine 
• 10017-11-5 allylammonium chloride 
• 128993-17-9 (5S)-3-Bromo-5-hydroxymethyl-Δ²-isoxazoline 

Downstream Products

• 1355358-62-1 (S)-4-ethynylbenzyl 2-((((S)-3-bromo-4,5-dihydroisoxazol-5-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate 
• 1355358-61-0 C₂₅H₂₂BrFN₄O₄ 
• 1355358-60-9 C₂₅H₂₃BrN₄O₅ 
• 1355358-59-6 C₂₅H₂₃BrN₄O₄ 
• 1355358-58-5 C₂₃H₂₂BrN₃O₅ 
• 1355358-57-4 C₁₇H₁₉BrN₆O₄ 
• 1355358-56-3 C₂₃H₂₁BrFN₇O₄ 
• 1355358-55-2 C₂₃H₂₂BrN₇O₅ 
• 1355358-53-0 C₂₃H₂₂BrN₇O₄ 
• 1355358-51-8 C₂₁H₂₁BrN₆O₅ 
• 120244-89-5 [(S)-1-[((S)-3-Bromo-4,5-dihydro-isoxazol-5-ylmethyl)-carbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester 

Relevant articles and documents

In vivo evaluation of two tissue transglutaminase PET tracers in an orthotopic tumour xenograft model

Background: The protein cross-linking enzyme tissue transglutaminase (TG2; EC 2.3.2.13) is associated with the pathogenesis of various diseases, including cancer. Recently, the synthesis and initial evaluation of two high-potential radiolabelled irreversible TG2 inhibitors were reported by us. In the present study, these two compounds were evaluated further in a breast cancer (MDA-MB-231) tumour xenograft model for imaging active tissue transglutaminase in vivo. Results: The metabolic stability of [11C]1 and [18F]2 in SCID mice was comparable to the previously reported stability in Wistar rats. Quantitative real-time polymerase chain reaction analysis on MDA-MB-231 cells and isolated tumours showed a high level of TG2 expression with very low expression of other transglutaminases. PET imaging showed low tumour uptake of [11C]1 (approx. 0.5 percentage of the injected dose per gram (%ID/g) at 40–60?min p.i.) and with relatively fast washout. Tumour uptake for [18F]2 was steadily increasing over time (approx. 1.7 %ID/g at 40–60?min p.i.). Pretreatment of the animals with the TG2 inhibitor ERW1041E resulted in lower tumour activity concentrations, and this inhibitory effect was enhanced using unlabelled 2. Conclusions: Whereas the TG2 targeting potential of [11C]1 in this model seems inadequate, targeting of TG2 using [18F]2 was achieved. As such, [18F]2 could be used in future studies to clarify the role of active tissue transglutaminase in disease.

Development of rhodesain inhibitors with a 3-bromoisoxazoline warhead

Novel rhodesain inhibitors were obtained by combining an enantiomerically pure 3-bromoisoxazoline warhead with a specific peptidomimetic recognition moiety. All derivatives behaved as inhibitors of rhodesain, with low micromolar Ki values. Their activity against the enzyme was found to be paralleled by an in vitro antitrypanosomal activity, with IC50 values in the mid-micromolar range. Notably, a preference for parasitic over human proteases, specifically cathepsins B and L, was observed. Awakened by the warhead: Novel rhodesain inhibitors with antitrypanosomal activity were developed by coupling a 3-bromoisoxazoline warhead to a suitable peptidomimetic recognition moiety. Copyright