Indole-3-glyoxylamideCAS# 5548-10-7 |
Quality Control & MSDS
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| Cas No. | 5548-10-7 | SDF | Download SDF |
| PubChem ID | 73227 | Appearance | Yellow powder |
| Formula | C10H8N2O2 | M.Wt | 188.18 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-(1H-indol-3-yl)-2-oxoacetamide | ||
| SMILES | C1=CC=C2C(=C1)C(=CN2)C(=O)C(=O)N | ||
| Standard InChIKey | AWMLDBKLOPNOAR-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C10H8N2O2/c11-10(14)9(13)7-5-12-8-4-2-1-3-6(7)8/h1-5,12H,(H2,11,14) | ||
| 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 | 1. Indole-3-glyoxylamides are an attractive lead series for continuing development as potential therapeutic agents against prion disease. 2. A number of Indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, exert a cytotoxic effect against multiple cancer cell lines. |
| Targets | Antifection |
Indole-3-glyoxylamide Dilution Calculator
Indole-3-glyoxylamide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.3141 mL | 26.5703 mL | 53.1406 mL | 106.2812 mL | 132.8515 mL |
| 5 mM | 1.0628 mL | 5.3141 mL | 10.6281 mL | 21.2562 mL | 26.5703 mL |
| 10 mM | 0.5314 mL | 2.657 mL | 5.3141 mL | 10.6281 mL | 13.2852 mL |
| 50 mM | 0.1063 mL | 0.5314 mL | 1.0628 mL | 2.1256 mL | 2.657 mL |
| 100 mM | 0.0531 mL | 0.2657 mL | 0.5314 mL | 1.0628 mL | 1.3285 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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Discovery of 6-substituted indole-3-glyoxylamides as lead antiprion agents with enhanced cell line activity, improved microsomal stability and low toxicity.[Pubmed:21726921]
Eur J Med Chem. 2011 Sep;46(9):4125-32.
A series of highly potent Indole-3-glyoxylamide based antiprion agents was previously characterized, focusing on optimization of structure-activity relationship (SAR) at positions 1-3 of the indole system. New libraries interrogating the SAR at indole C-4 to C-7 now demonstrate that introducing electron-withdrawing substituents at C-6 may improve biological activity by up to an order of magnitude, and additionally confer higher metabolic stability. For the present screening libraries, both the degree of potency and trends in SAR were consistent across two cell line models of prion disease, and the large majority of compounds showed no evidence of toxic effects in zebrafish. The foregoing observations thus make the Indole-3-glyoxylamides an attractive lead series for continuing development as potential therapeutic agents against prion disease.
Didemnidines A and B, indole spermidine alkaloids from the New Zealand ascidian Didemnum sp.[Pubmed:21348447]
J Nat Prod. 2011 Apr 25;74(4):888-92.
Two new indole spermidine alkaloids, didemnidines A (1) and B (2), have been isolated from the New Zealand ascidian Didemnum sp. The structures of the metabolites, determined by analysis of 2D NMR spectra and confirmed via synthesis, embody an Indole-3-glyoxylamide moiety linked to the N(1) position of spermidine, the latter motif being particularly rare among marine natural products. Didemnidine B and a synthetic precursor exhibited mild in vitro growth inhibition of Plasmodium falciparum with IC(50)'s of 15 and 8.4 muM, respectively.
An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer.[Pubmed:26580420]
J Med Chem. 2015 Dec 10;58(23):9309-33.
A number of Indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of reducing aromatic ring count and introducing a greater degree of saturation, which retain potent tubulin polymerization activity but with a distinct SAR from previously documented libraries. A subset of active compounds from the reported series is shown to interact with tubulin at the colchicine binding site, disrupt the cellular microtubule network, and exert a cytotoxic effect against multiple cancer cell lines. Two compounds demonstrated significant tumor growth inhibition in a mouse xenograft model of head and neck cancer, a type of the disease which often proves resistant to chemotherapy, supporting further development of the current series as potential new therapeutics.
