O-(Benzotriazol-1-yl)-N,N,N',N'-tetra methyluronium tetrafluoroborate
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O-(Benzotriazol-1-yl)-N,N,N',N'-tetra methyluronium tetrafluoroborate

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O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate is used in the synthesis of tetrapeptoid analogues of the antiprotocoal compound Apicidin. Also used in the synthesis of acid based t-antigen glycodendrimers.

Category
Peptide Synthesis Reagents
Catalog number
BAT-002414
CAS number
125700-67-6
Molecular Formula
C11H16N5O.BF4
Molecular Weight
321.08
O-(Benzotriazol-1-yl)-N,N,N',N'-tetra methyluronium tetrafluoroborate
IUPAC Name
[benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate
Synonyms
1-[Bis(dimethylamino)methylene]-1H-benzotriazolium 3-Oxide Tetrafluoroborate(1-) (1:1); 1-[Bis(dimethylamino)methylene]-1H-benzotriazolium 3-Oxide Tetrafluoroborate(1-); O-Benzotriazolyl Tetramethylisouronium Tetrafluoroborate; TBTU; 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; 2-(1h-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; o-(1h-benzotriazol-1-yl)-n,n,n',n'-tetramethyluronium tetrafluoroborate; MFCD00077413; N,N,N',N'-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate; O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
Appearance
White crystalline powder
Purity
99 % (HPLC)
Melting Point
205 °C (dec.)
Storage
2-8 °C
Solubility
Soluble in Acetonitrile (100 mg/ml, clear, colorless), DMF (160.55 mg/ml, clear), Water (3 mg/ml at 20 °C)
InChI
InChI=1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1
InChI Key
JKEKMBGUVUKMQB-UHFFFAOYSA-N
Canonical SMILES
[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
1. Novel glycosylated endomorphin-2 analog produces potent centrally-mediated antinociception in mice after peripheral administration
Jakub Fichna, et al. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6673-6. doi: 10.1016/j.bmcl.2013.10.041. Epub 2013 Oct 30.
We report the synthesis and pharmacological characterization of a novel glycosylated analog of a potent and selective endogenous μ-opioid receptor (MOP) agonist, endomorphin-2 (Tyr-Pro-Phe-Phe-NH2, EM-2), obtained by the introduction in position 3 of the tyrosine residue possessing the glucose moiety attached to the phenolic function via a β-glycosidic bond. The improved blood-brain barrier permeability and enhanced antinociceptive effect of the novel glycosylated analog suggest that it may be a promising template for design of potent analgesics. Furthermore, the described methodology may be useful for increasing the bioavailability and delivery of opioid peptides to the CNS.
2. Novel state-dependent voltage-gated sodium channel modulators, based on marine alkaloids from Agelas sponges
Žiga Hodnik, Tihomir Tomašić, Lucija Peterlin Mašič, Fiona Chan, Robert W Kirby, David J Madge, Danijel Kikelj Eur J Med Chem. 2013;70:154-64. doi: 10.1016/j.ejmech.2013.07.034. Epub 2013 Aug 11.
Clathrodin, alkaloid isolated from Agelas sponges, was reported in 1995 as a voltage-gated sodium channel modulator. Here we describe the design and synthesis of conformationally restricted clathrodin analogues incorporating the 4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine moiety and evaluation of their modulatory activities on human voltage-gated sodium channel isoforms Na(v)1.3, Na(v)1.4 and Na(v)1.7, as well as their selectivity against cardiac isoform Na(v)1.5. Compounds were shown to act as state-dependent modulators of Na(v)1.3, Na(v)1.4 and Na(v)1.7 with IC₅₀ values in the lower micromolar range for the open-inactivated state of the channels. Preliminary structure-activity relationship studies have revealed the importance of hydrophobic interactions for binding to all three tested isoforms. Compound 4e with IC₅₀ value of 8 μM against Na(v)1.4 represents a novel selective state-dependent Na(v)1.4 channel modulator.
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