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CAS No. : | 59-14-3 | MDL No. : | MFCD00006529 |
Formula : | C9H11BrN2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WOVKYSAHUYNSMH-RRKCRQDMSA-N |
M.W : | 307.10 | Pubchem ID : | 6035 |
Synonyms : |
BrdU;5-Bromo-2'-deoxyuridine;NSC 38297;Broxuridine;Bromodeoxyuridine;BUdR
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 60.81 |
TPSA : | 104.55 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.38 cm/s |
Log Po/w (iLOGP) : | 1.26 |
Log Po/w (XLOGP3) : | -0.29 |
Log Po/w (WLOGP) : | -1.38 |
Log Po/w (MLOGP) : | -1.14 |
Log Po/w (SILICOS-IT) : | 0.18 |
Consensus Log Po/w : | -0.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.69 |
Solubility : | 6.26 mg/ml ; 0.0204 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.45 |
Solubility : | 11.0 mg/ml ; 0.0358 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.89 |
Solubility : | 39.3 mg/ml ; 0.128 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
86% | With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.2 h; | General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4percent–6percent MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93percent) in pure form as a white solid. |
80% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 0.75 h; | Typical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75percent) as colorless crystals with data as reported.14 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose In aq. buffer at 30℃; Green chemistry; Enzymatic reaction | General procedure: Thymidine (dThd) and 2'-deoxyuridine (dUrd) were assayed as sugar donors. Different purine and pyrimidine bases were tested: 5-fluorouracil (5FUra), 5-bromouracil (5BrUra), 5-chlorouracil (5ClUra), 6-chloropurine (6ClPur), 6-bromopurine (6BrPur) and 6-chloro-2-fluoropurine (6Cl2FPur). Reactions were performed using 100 mg/mL of immobilized LaNDT, 6 mM nucleoside and 2 mM base, 30 °C and 200 rpm. At different times (5–8 h), 20 μL aliquots were taken and centrifuged at 10,000 x g, and the supernatant was analyzed by HPLC to evaluate yield expressed as percentage and product conversion expressed as mg of product per gram of support. |