6-BenzyloxypurineCAS# 57500-07-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 57500-07-9 | SDF | Download SDF |
| PubChem ID | 853677 | Appearance | Powder |
| Formula | C12H10N4O | M.Wt | 226 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 6-phenylmethoxy-7H-purine | ||
| SMILES | C1=CC=C(C=C1)COC2=NC=NC3=C2NC=N3 | ||
| Standard InChIKey | ZZZXGPGVDJDFCJ-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C12H10N4O/c1-2-4-9(5-3-1)6-17-12-10-11(14-7-13-10)15-8-16-12/h1-5,7-8H,6H2,(H,13,14,15,16) | ||
| 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. | ||
6-Benzyloxypurine Dilution Calculator
6-Benzyloxypurine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.4248 mL | 22.1239 mL | 44.2478 mL | 88.4956 mL | 110.6195 mL |
| 5 mM | 0.885 mL | 4.4248 mL | 8.8496 mL | 17.6991 mL | 22.1239 mL |
| 10 mM | 0.4425 mL | 2.2124 mL | 4.4248 mL | 8.8496 mL | 11.0619 mL |
| 50 mM | 0.0885 mL | 0.4425 mL | 0.885 mL | 1.7699 mL | 2.2124 mL |
| 100 mM | 0.0442 mL | 0.2212 mL | 0.4425 mL | 0.885 mL | 1.1062 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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A strategy for selective O(6)-alkylguanine-DNA alkyltransferase depletion under hypoxic conditions.[Pubmed:22553921]
Chem Biol Drug Des. 2012 Aug;80(2):279-90.
Cellular resistance to chemotherapeutics that alkylate the O-6 position of guanine residues in DNA correlates with their O(6)-alkylguanine-DNA alkyltransferase activity. In normal cells high [O(6)-alkylguanine-DNA alkyltransferase] is beneficial, sparing the host from toxicity, whereas in tumor cells high [O(6)-alkylguanine-DNA alkyltransferase] prevents chemotherapeutic response. Therefore, it is necessary to selectively inactivate O(6)-alkylguanine-DNA alkyltransferase in tumors. The oxygen-deficient compartment unique to solid tumors is conducive to reduction, and could be utilized to provide this selectivity. Therefore, we synthesized 2-nitro-6-Benzyloxypurine, an analog of O(6)-benzylguanine in which the essential 2-amino group is replaced by a nitro moiety, and 2-nitro-6-Benzyloxypurine is >2000-fold weaker than O(6)-benzylguanine as an O(6)-alkylguanine-DNA alkyltransferase inhibitor. We demonstrate oxygen concentration sensitive net reduction of 2-nitro-6-Benzyloxypurine by cytochrome P450 reductase, xanthine oxidase, and EMT6, DU145, and HL-60 cells to yield O(6)-benzylguanine. We show that 2-nitro-6-Benzyloxypurine treatment depletes O(6)-alkylguanine-DNA alkyltransferase in intact cells under oxygen-deficient conditions and selectively sensitizes cells to laromustine (an agent that chloroethylates the O-6 position of guanine) under oxygen-deficient but not normoxic conditions. 2-Nitro-6-Benzyloxypurine represents a proof of concept lead compound; however, its facile reduction (E(1/2) - 177 mV versus Ag/AgCl) may result in excessive oxidative stress and/or the generation of O(6)-alkylguanine-DNA alkyltransferase inhibitors in normoxic regions in vivo.
Design, synthesis, and antiviral evaluation of purine-beta-lactam and purine-aminopropanol hybrids.[Pubmed:22519297]
J Med Chem. 2012 Jun 14;55(11):5637-41.
Purine-beta-lactam chimera were prepared as a novel class of hybrid systems through N-alkylation of 6-benzylamino- or 6-Benzyloxypurine with (omega-haloalkyl)-beta-lactams, followed by reductive ring opening of the beta-lactam ring by LiEt(3)BH to provide an entry into the class of purine-aminopropanol hybrids. Both new types of hybrid systems were assessed for their antiviral activity and cytotoxicity, resulting in the identification of eight purine-beta-lactam hybrids and two purine-aminopropanol hybrids as promising lead structures.
Synthesis of 2'-substituted inosine analogs via unusual masking of the 6-hydroxyl group.[Pubmed:22356237]
Nucleosides Nucleotides Nucleic Acids. 2012;31(3):224-35.
2'-Modified inosine analogs have been synthesized from 6-chloropurine riboside via 6-dimethylaminopurine or 6-Benzyloxypurine intermediates. The dimethylaminopurine intermediate was obtained via an unusually facile dimethylamine transfer from dimethylformamide. Graphical Abstract:
