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3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER - CAS 219943-38-1

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Category
Main Product
Product Name
3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
Catalog Number
219943-38-1
Synonyms
3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER; 3,4-DIBROMOINDOLE, N-BOC PROTECTED; 3,4-Dibromo-1H-indole, N-BOC protected; 3,4-Dibromo-1H-indole-1-carboxylic acid tert-butyl ester; 3,4-Dibromo-1H-indole, N-BOC protected 98%; 1-Boc-3,4-dibromoindole
CAS Number
219943-38-1
Molecular Weight
375.06
Molecular Formula
C13H13Br2NO2
COA
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MSDS
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Canonical SMILES
CC(C)(C)OC(=O)N1C=C(C2=C1C=CC=C2Br)Br
InChI
InChI=1S/C13H13Br2NO2/c1-13(2,3)18-12(17)16-7-9(15)11-8(14)5-4-6-10(11)16/h4-7H,1-3H3
InChIKey
WOKVBYGNVGDARB-UHFFFAOYSA-N
Structure
CAS 219943-38-1 3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
Specification
Purity
95%
Boiling Point
414.5ºC at 760mmHg
Density
1.64g/cm3
Reference Reading
1.Efflux transport of chrysin and apigenin sulfates in HEK293 cells overexpressing SULT1A3: The role of multidrug resistance-associated protein 4 (MRP4/ABCC4).
Li W1, Sun H1, Zhang X1, Wang H1, Wu B2. Biochem Pharmacol. 2015 Nov 1;98(1):203-14. doi: 10.1016/j.bcp.2015.08.090. Epub 2015 Aug 17.
Efflux transport is a critical determinant to the pharmacokinetics of sulfate conjugates. Here we aimed to establish SULT1A3 stably transfected HEK293 cells, and to determine the contributions of BCRP and MRP transporters to excretion of chrysin and apigenin sulfates. The cDNA of SULT1A3 was stably introduced into HEK293 cells using a lentiviral vector, generating a sulfonation active cell line (i.e., SULT293 cells). Identification of sulfate transporters was achieved through chemical inhibition (using chemical inhibitors) and biological inhibition (using short-hairpin RNAs (shRNAs)) methods. Sulfated metabolites were rapidly generated and excreted upon incubation of SULT293 cells with chrysin and apigenin. Ko143 (a selective BCRP inhibitor) did not show inhibitory effects on sulfate disposition, whereas the pan-MRP inhibitor MK-571 caused significant reductions (38.5-64.3%, p<0.001) in sulfate excretion and marked elevations (160-243%, p<0.
2.A fast isocratic liquid chromatography method for the quantification of xanthophylls and their stereoisomers.
Nimalaratne C1, Lopes-Lutz D1, Schieber A1,2, Wu J1. J Sep Sci. 2015 Dec;38(24):4166-72. doi: 10.1002/jssc.201500656. Epub 2015 Nov 12.
A fast isocratic liquid chromatography method was developed for the simultaneous quantification of eight xanthophylls (13-Z-lutein, 13'-Z-lutein, 13-Z-zeaxanthin, all-E-lutein, all-E-zeaxanthin, all-E-canthaxanthin, all-E-β-apo-8'-carotenoic acid ethyl ester and all-E-β-apo-8'-carotenal) within 12 min, compared to 90 min by the conventional high-performance liquid chromatography method. The separation was achieved on a YMC C30 reversed-phase column (100 mm x 2.0 mm; 3 μm) operated at 20°C using a methanol/tert-butyl methyl ether/water solvent system at a flow rate of 0.8 mL/min. The method was successfully applied to quantify lutein and zeaxanthin stereoisomers in egg yolk, raw and cooked spinach, and a dietary supplement. The method can be used for the rapid analysis of xanthophyll isomers in different food products and for quality control purposes.
3.Synthesis and biological evaluation of new C-10 substituted dithranol pleiotropic hybrids.
Bariamis SE1, Magoulas GE1, Grafanaki K2, Pontiki E3, Tsegenidis T1, Athanassopoulos CM1, Maroulis G1, Papaioannou D4, Hadjipavlou-Litina D5. Bioorg Med Chem. 2015 Nov 15;23(22):7251-63. doi: 10.1016/j.bmc.2015.10.022. Epub 2015 Oct 23.
Selective alkylation of the antipsoriatic drug dithranol (DTR) at C-10 with tert-butyl bromoacetate, followed by acid-mediated deprotection, produced the corresponding carboxylic acid 4 which was coupled with selectively protected polyamines (PAs), such as putrescine (PUT), spermidine (SPD) and spermine (SPM), dopamine and aliphatic amines and substituted benzylamines producing a series of DTR-PA hybrids, after acid-mediated deprotection, as well as simple amides. The compounds were tested as antioxidants and inhibitors of lipoxygenase (LOX). The amides 4,4'-dimethoxybenzhydrylamide 13 (86% and 95%), 2,4-dimethoxybenzylamide 12 (87% and 81%) and dodecylamide 9 (98% and 74%), and the hybrid DTR-SPM (7) (93% and 87%), showed the highest antioxidant activity in the DPPH and AAPH assays, whereas the most potent inhibitors of LOX were amide 13 (IC50=7 μM), the benzylamide 10 (IC50=7.9 μM) and the butylamide 8 (IC50=10 μM). Molecular binding studies showed that binding of these derivatives into the hydrophobic domain blocks approach of substrate to the active site, inhibiting soybean LOX.
4.C1, a highly potent novel curcumin derivative, binds to tubulin, disrupts microtubule network and induces apoptosis.
Srivastava S1, Mishra S2, Surolia A3, Panda D4. Biosci Rep. 2016 Mar 15. pii: BSR20160039. [Epub ahead of print]
We have synthesized a curcumin derivative, 4-{5-(4-Hydroxy-3-methoxy-phenyl)-2-[3-(4-hydroxy-3-methoxy-phenyl)-acryloyl]-3-oxo-penta-1,4-dienyl}-piperidine-1-carboxylic acid tert-butyl ester (C1) that displays much stronger antiproliferative activity against various types of cancer cells including multidrug resistance cells than curcumin. C1 depolymerized both interphase and mitotic microtubules in MCF-7 cells and also inhibited the reassembly of microtubules in these cells. C1 inhibited the polymerization of purified tubulin, disrupted the lattice structure of microtubules and suppressed their GTPase activity in vitro. The compound bound to tubulin with a dissociation constant of 2.8 ±1 µM and perturbed the secondary structures of tubulin. Further, C1 treatment reduced the expression of Bcl2, increased the expression of Bax and down regulated the level of a key regulator of p53, Mdm2 (S166), in MCF-7 cells. C1 appeared to induce p53 mediated apoptosis in MCF-7 cells.
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