1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanoneNF-κB pathway inhibitor CAS# 758679-97-9 |
![1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone](/media/images/struct/BCC1481.png "1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone")
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 758679-97-9 | SDF | Download SDF |
| PubChem ID | 2858523 | Appearance | Powder |
| Formula | C28H39N3O3 | M.Wt | 465.63 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 20 mM in DMSO and to 20 mM in ethanol | ||
| Chemical Name | 1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-[2-(3-hydroxypropylamino)-5,6-dimethylbenzimidazol-1-yl]ethanone | ||
| SMILES | CC1=CC2=C(C=C1C)N(C(=N2)NCCCO)CC(=O)C3=CC(=C(C(=C3)C(C)(C)C)O)C(C)(C)C | ||
| Standard InChIKey | CYCGGKILBWERDJ-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C28H39N3O3/c1-17-12-22-23(13-18(17)2)31(26(30-22)29-10-9-11-32)16-24(33)19-14-20(27(3,4)5)25(34)21(15-19)28(6,7)8/h12-15,32,34H,9-11,16H2,1-8H3,(H,29,30) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Selectively inhibits protein kinase C (PKC)-induced activation of the NF-κB pathway (IC50 < 0.1 μM for PMA-stimulated IL-8 production). Inhibits antigen receptor-stimulated NF-κB activation in chronic lymphocytic leukemia (CLL) B cells. Does not inhibit other NF-κB pathways, including that activated by tumor necrosis factor (TNF). |
1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone Dilution Calculator
1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1476 mL | 10.7381 mL | 21.4763 mL | 42.9526 mL | 53.6907 mL |
| 5 mM | 0.4295 mL | 2.1476 mL | 4.2953 mL | 8.5905 mL | 10.7381 mL |
| 10 mM | 0.2148 mL | 1.0738 mL | 2.1476 mL | 4.2953 mL | 5.3691 mL |
| 50 mM | 0.043 mL | 0.2148 mL | 0.4295 mL | 0.8591 mL | 1.0738 mL |
| 100 mM | 0.0215 mL | 0.1074 mL | 0.2148 mL | 0.4295 mL | 0.5369 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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CID-2858522, a 2-aminobenzimidazole compound, selectively inhibits the NF-κB pathway (IC50 < 0.1 μM for PMA-stimulated IL-8 production) induced by PKC, operating downstream of PKC but upstream of IKKbeta, without inhibiting other NF-kappaB activation pathways.
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Chemical biology strategy reveals pathway-selective inhibitor of NF-kappaB activation induced by protein kinase C.[Pubmed:20141195]
ACS Chem Biol. 2010 Mar 19;5(3):287-99.
Dysregulation of NF-kappaB activity contributes to many autoimmune and inflammatory diseases. At least nine pathways for NF-kappaB activation have been identified, most of which converge on the IkappaB kinases (IKKs). Although IKKs represent logical targets for potential drug discovery, chemical inhibitors of IKKs suppress all known NF-kappaB activation pathways and thus lack the selectivity required for safe use. A unique NF-kappaB activation pathway is initiated by protein kinase C (PKC) that is stimulated by antigen receptors and many growth factor receptors. Using a cell-based high-throughput screening (HTS) assay and chemical biology strategy, we identified a 2-aminobenzimidazole compound, CID-2858522, which selectively inhibits the NF-kappaB pathway induced by PKC, operating downstream of PKC but upstream of IKKbeta, without inhibiting other NF-kappaB activation pathways. In human B cells stimulated through surface immunoglobulin, CID-2858522 inhibited NF-kappaB DNA-binding activity and expression of endogenous NF-kappaB-dependent target gene, TRAF1. Altogether, as a selective chemical inhibitor of the NF-kappaB pathway induced by PKC, CID-2858522 serves as a powerful research tool and may reveal new paths toward therapeutically useful NF-kappaB inhibitors.
Inhibition of protein kinase C-driven nuclear factor-kappaB activation: synthesis, structure-activity relationship, and pharmacological profiling of pathway specific benzimidazole probe molecules.[Pubmed:20481485]
J Med Chem. 2010 Jun 24;53(12):4793-7.
A unique series of biologically active chemical probes that selectively inhibit NF-kappaB activation induced by protein kinase C (PKC) pathway activators have been identified through a cell-based phenotypic reporter gene assay. These 2-aminobenzimidazoles represent initial chemical tools to be used in gaining further understanding on the cellular mechanisms driven by B and T cell antigen receptors. Starting from the founding member of this chemical series 1a (notated in PubChem as CID-2858522), we report the chemical synthesis, SAR studies, and pharmacological profiling of this pathway-selective inhibitor of NF-kappaB activation.
