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[ CAS No. 59-14-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 59-14-3
Chemical Structure| 59-14-3
Structure of 59-14-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 59-14-3 ]

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

Calculated chemistry of [ 59-14-3 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.57

Safety of [ 59-14-3 ]

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:

Application In Synthesis of [ 59-14-3 ]

* 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.

  • Upstream synthesis route of [ 59-14-3 ]
  • Downstream synthetic route of [ 59-14-3 ]

[ 59-14-3 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 951-78-0 ]
  • [ 59-14-3 ]
YieldReaction ConditionsOperation 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
Reference: [1] Synthesis, 2009, # 23, p. 3957 - 3962
[2] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[3] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834
[4] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[5] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[6] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3333 - 3336
[7] Tetrahedron Letters, 1992, vol. 33, # 50, p. 7779 - 7782
[8] Journal of the American Chemical Society, 1955, vol. 77, p. 736
[9] Journal of the American Chemical Society, 1955, vol. 77, p. 4279,4285
[10] Recueil: Journal of the Royal Netherlands Chemical Society, 1981, vol. 100, # 7/8, p. 267 - 271
  • 2
  • [ 51-20-7 ]
  • [ 50-89-5 ]
  • [ 59-14-3 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Journal of Fluorine Chemistry, 2016, vol. 186, p. 91 - 96
  • 3
  • [ 51-20-7 ]
  • [ 951-78-0 ]
  • [ 59-14-3 ]
  • [ 66-22-8 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 16 - 22
  • 4
  • [ 6161-23-5 ]
  • [ 59-14-3 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[2] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834
  • 5
  • [ 51-20-7 ]
  • [ 59-14-3 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2642 - 2645
  • 6
  • [ 123760-35-0 ]
  • [ 59-14-3 ]
  • [ 123760-37-2 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 29, p. 3819 - 3820
  • 7
  • [ 123760-35-0 ]
  • [ 59-14-3 ]
  • [ 123739-80-0 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 29, p. 3819 - 3820
  • 8
  • [ 54-42-2 ]
  • [ 951-78-0 ]
  • [ 59-14-3 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5721 - 5724
  • 9
  • [ 51-20-7 ]
  • [ 1463-10-1 ]
  • [ 59-14-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 79, p. 49 - 53
  • 10
  • [ 951-77-9 ]
  • [ 59-14-3 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 736
  • 11
  • [ 51-20-7 ]
  • [ 50-89-5 ]
  • [ 59-14-3 ]
  • [ 65-71-4 ]
Reference: [1] Chemistry Letters, 2006, vol. 35, # 2, p. 232 - 233
  • 12
  • [ 13030-62-1 ]
  • [ 59-14-3 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
  • 13
  • [ 146629-34-7 ]
  • [ 59-14-3 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 6, p. 513 - 522
  • 14
  • [ 75-77-4 ]
  • [ 598-73-2 ]
  • [ 54-42-2 ]
  • [ 951-78-0 ]
  • [ 59-14-3 ]
  • [ 70523-31-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1982, vol. 25, # 11, p. 1329 - 1334
  • 15
  • [ 130328-09-5 ]
  • [ 130328-11-9 ]
  • [ 59-14-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2590 - 2595
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