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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Uracil is one of the four nucleobases in the nucleic acid of RNA can be used for drug delivery and as a pharmaceutical.
Synonyms: 4-Hydroxyuracil; NSC 3970; Pyrod.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 66-22-8 |
Formula : | C4H4N2O2 |
M.W : | 112.09 |
SMILES Code : | O=C1NC(C=CN1)=O |
Synonyms : |
4-Hydroxyuracil; NSC 3970; Pyrod.
|
MDL No. : | MFCD00006016 |
InChI Key : | ISAKRJDGNUQOIC-UHFFFAOYSA-N |
Pubchem ID : | 1174 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.26% | 10081] A mixture of uracil (0.112 g, 1 mmol), K2C03 (0.276 g, 2 mmol) and KI (ca. 25mg, a catalytic amount) in 10 mE of DMSO was stirred under N2 for 10 mi 4-(bromom- ethyl)-4?-methyl-2,2?-bipyridine (0.644 g, 2.45 mmol) predissolved in DMSO (5 mE) was then slowly added via a syringe and the resultant chocolate brown mixture was stirred under N2 at room temperature for 3 h. Water (100 mE) was then added and the suspension was extracted with dichloromethane. The collected organic layers were dried over anhydrous sodium sulphate and solvent was removed in vacuum to give a half-white solid. The crude was subjected to the silica column chromatography using dichioromethane and acetone as eluent 99:1% (v/v). The second spot on the TEC plate was collected as E2 (0.145 g, 49.26%). Electron impact (El) mass spectrum: mlz=3 16.91 [E2+Na]; ?H NMR (200 MHz, MeOD) OH 8.65 (d, 1H, J=5.7 Hz), 8.52 (d, 1H, J=4.8 Hz), 8.24-8.18 (2H, m), 7.73 (d, 1H, J=7.9 Hz), 7.38 (d, 1H, J=3.4 Hz), 7.32 (d, 1H, J=6.6 Hz), 5.77 (d, 1H, J=7.9 Hz),5.10 (2H, s), 2.49 (3H, s). (Refer FIG. 9, 10) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.18 mg; 0.07 mg; 0.03 mg; 1.9 mg; 0.21 mg; 0.11 mg; 0.18 mg; 0.18 mg; 0.73 mg; 0.22 mg; 0.01 mg; 0.57 mg; 0.27 mg; 0.02 mg | With ferric sulfate nonahydrate; In water; at 80℃; for 24h;pH 7.57; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 muL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0% w/w) at 80 C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 muL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0% w/w ofthe corresponding salt?s pellet) at 80 C for 24 h. For the innerenvironment, NH2CHO (200 muL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0% w/w) at80 C for 24 h. The reaction of NH2CHO (10% v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 muL) at 60C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 C, detector temperature 280 C, gradient 100 C for 2min, and 10 C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98% compared to that of the reference standards.The analysis was limited to products of ?1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.17 mg; 0.05 mg; 0.03 mg; 1.8 mg; 0.17 mg; 0.11 mg; 0.15 mg; 0.12 mg; 0.7 mg; 0.23 mg; 0.01 mg; 0.53 mg; 0.23 mg | With magnesium sulfate; In water; at 80℃; for 24h;pH 7.57; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 muL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0% w/w) at 80 C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 muL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0% w/w ofthe corresponding salt?s pellet) at 80 C for 24 h. For the innerenvironment, NH2CHO (200 muL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0% w/w) at80 C for 24 h. The reaction of NH2CHO (10% v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 muL) at 60C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 C, detector temperature 280 C, gradient 100 C for 2min, and 10 C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98% compared to that of the reference standards.The analysis was limited to products of ?1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9 mg; 1.3 mg; 1.1 mg; 0.8 mg; 5.9 mg; 2.0 mg; 1.0 mg; 2.1 mg; 2.3 mg; 1.1 mg; 1.1 mg; 0.9 mg; 1.1 mg; 1.2 mg; 1.7 mg | With Angelica sinensis (Oliv.) Diels callus; In methanol; for 168.0h; | General procedure: Isofraxetin-6-O-beta-D-glucopyranoside (859 mg) was dissolved in CH3OH (86.0 mL) and distributed into 59 bottles of the suspension cultures of A. sinensis callus equally. The mixture was co-cultured for 7 days, then the cells and medium were separated by filtration. The medium was concentrated to 200 mL and partitioned by the same volume of EtOAc (ethylacetate) and n-BuOH (n-butyl alcohol) successively for three times. Next, the organic phase was collected and concentrated under the reduced pressure toyield EtOAc extract (Fr. 1, 0.25 g) and n-BuOH extract (Fr. 2, 1.20 g) respectively. The cells were dried under 50C, and then were extracted in an ultrasonic bath with CH3OH for 30 min. After that, the extract was further partitioned by EtOAc and n-BuOH respectively to afford EtOAc extract (Fr. 3,0.62 g) and n-BuOH extract (Fr. 4, 1.46 g). Compared with the experimental group, cultures and medium without isofraxetin-6-O-b-D-glucopyranoside act as control group and was processed to get Fr. 5-8 by the same procedures. The combination of Fr. 1 and Fr. 3 (EE, 0.87 g) was subjected on ODS column chromatography (CC) with gradient elution CH3OH/H2O (from 0:100 to 100:0) to get five subfractions (Fr. 1a-5a). Next, Fr. 1a was separated by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) eluted with CH3OH/H2O(49: 51) to afford compounds 5 (2.1 mg, tR = 14 min), 6 (2.3 mg, tR = 18 min)and 3 (5.9 mg, tR = 39 min). Fr. 2a was firstly fractioned by silica gel CC(3 50 cm) with gradient elution petroleum/acetone (0:100-100:0) to get substraction 2a-1 and 2a-2. Then Fr. 2a-1 was purified by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O (37: 63) to provide compounds 8 (1.0 mg, tR = 22 min), 10 (1.1 mg, tR = 27 min) and 14(1.2 mg, tR = 35 min). While compound 15 (0.9 mg, tR = 25 min) was purifiedfrom substration Fr. 2a-2, using HPLC with ODS column (250 mm 10 mm,flow rate 3 mL/min) eluted with CH3CN/H2O (39: 61). And Fr. 3a was chromatographied on HPLC with ODS column (250 mm 10 mm, flow rate3 mL/min) to yield compounds 9 (1.1 mg, tR = 40 min) and 11 (0.9 mg,tR = 56 min) using CH3OH/H2O (35: 65) as elute. However, compounds 12(0.8 mg, tR = 37 min) and 13 (1.3 mg, tR = 49 min) were obtained from Fr. 4a byHPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) using CH3CN/H2O (8:92) as eluting solvent. Equally, Fr. 2 and Fr. 4 was combined as BE(2.66 g) to subject on ODS CC with CH3OH/H2O (from 0:100 to 100:0) to getseven fractions (Fr. 1b-7b). Fr. 1b was isolated using HPLC with ODS column(250 mm 10 mm, flow rate 3 mL/min) eluted by CH3OH/H2O (20: 80) andthen purified by Sephadex LH-20 chromatography eluted with CH3OH to afford compounds 1 (1.1 mg) and 2 (1.7 mg). Furthermore, compound 4 (2.0 mg) wasobtained from Fr. 3b by recrystallization in CH3OH. Next, Fr. 4b was subjectedon silica gel CC (3 50 cm) with gradient elution CH2Cl2/CH3OH (0:100-100:0)to get substraction Fr. 4b-1 and Fr. 4b-2. Then Fr. 4b-1 was purified by HPLCwith ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O(13: 87) to provide compounds 7 (1.1 mg, tR = 19 min) and 16 (1.8 mg,tR = 39 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: To a double-necked round bottom flask (100mL), equipped with a condenser, it was added a mixture of KI (1.5mmol), P2O5 (1.5mmol) and the desired alcohol (1mmol) in DMF (5mL). The reaction mixture was stirred at r.t. for 30min. Next, the considered nucleobase (1mmol), K2CO3 (1mmol) and Et3N (1mmol) were added and the reaction mixture was heated to reflux for a further 6.5-10.5h (until TLC indicated no further progress in reaction, Table5). The solvent was then evaporated at reduced pressure, and the remaining foam was dissolved in chloroform (150mL) and washed with water (2×150mL). The organic layer was dried on Na2SO4 (1g) and evaporated. The product was purified using short column chromatography on silica gel eluting with proper solvents. |