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[ CAS No. 2353-33-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2353-33-5
Chemical Structure| 2353-33-5
Structure of 2353-33-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2353-33-5 ]

CAS No. :2353-33-5 MDL No. :
Formula : C8H12N4O4 Boiling Point : -
Linear Structure Formula :- InChI Key :XAUDJQYHKZQPEU-KVQBGUIXSA-N
M.W : 228.21 Pubchem ID :451668
Synonyms :
5-Aza-2'-deoxycytidine;5-AZA-CdR;US brand name: Dacogen. Abbreviations: 5AZA;dezocitidine;deoxyazacytidine;5-aza-dCyd;5-aza-2’-Deoxycytidine;DAC;NSC 127716

Calculated chemistry of [ 2353-33-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.62
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 52.48
TPSA : 123.49 Ų

Pharmacokinetics

GI absorption : Low
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) : -9.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : -1.89
Log Po/w (WLOGP) : -2.46
Log Po/w (MLOGP) : -2.61
Log Po/w (SILICOS-IT) : -1.84
Consensus Log Po/w : -1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.21
Solubility : 141.0 mg/ml ; 0.617 mol/l
Class : Very soluble
Log S (Ali) : -0.18
Solubility : 150.0 mg/ml ; 0.656 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.58
Solubility : 860.0 mg/ml ; 3.77 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.46

Safety of [ 2353-33-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2353-33-5 ]

* 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 [ 2353-33-5 ]
  • Downstream synthetic route of [ 2353-33-5 ]

[ 2353-33-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 2353-33-5 ]
  • [ 931-86-2 ]
  • [ 452-51-7 ]
Reference: [1] Patent: US2006/205685, 2006, A1, . Location in patent: Page/Page column 4; sheet 3
  • 2
  • [ 52523-35-0 ]
  • [ 80184-05-0 ]
  • [ 2353-33-5 ]
YieldReaction ConditionsOperation in experiment
89.3%
Stage #1: With cobalt(II) nitrate; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 60℃; Inert atmosphere
Stage #2: With triethylamine In N,N-dimethyl-formamide at 40℃;
1) Under nitrogen protection,will1-Chloro-2-deoxy-D-ribofuranose (15.3 g, 100 mmol)Cobalt nitrate(60 mmol),(R) -1,1'-bi-2-naphthol (15.7 g, 55 mmol) were added to 150 ml of DMF, stirred and mixed at 60 ° C for 1-2 hours, then cooled to room temperature,Filtered to give a mixture M containing 1-chloro-2-deoxy-D-ribofuranose complex;2) 11.1 g (110 mmol) of triethylamine,2,4-bis-trimethylSilicon-S-triazine(200 mmol)Into the mixture M obtained in the step 1) for 6 to 8 hours while stirring at 40 ° C,Dumped into the water,Dichloromethane extraction,2M & lt; / RTI & gt; HCl,Washed with saturated sodium bicarbonate,Concentrated and recrystallized from ethanol to obtain 20.4 g of decitabine in a yield of 89.3percent and a purity of 99.57percent.
87.2%
Stage #1: With (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride In N,N-dimethyl-formamide at 60℃; Inert atmosphere
Stage #2: With triethylamine In N,N-dimethyl-formamide at 40℃; for 6 h;
In the preparation method of decitabine according to Example 1,Except that the amount of palladium dichloride used was 17.7 g,19.9 g of decitabine was obtained,The yield was 87.2percentPurity 96.48percent.
Reference: [1] Patent: CN106046089, 2016, A, . Location in patent: Paragraph 0026; 0027; 0028; 0029
[2] Patent: CN106117290, 2016, A, . Location in patent: Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032-0061
  • 3
  • [ 1034301-08-0 ]
  • [ 2353-33-5 ]
YieldReaction ConditionsOperation in experiment
100% Alcoholic medium Example 2 The compound corresponding to formula (III) as obtained in Example 1 is further treated with in an alcoholic solution of ammonia in a known manner so that 2'-deoxy-5-azacytidine (Decitabine) is obtained in practically quantitative yield.
71.6% at 25℃; for 3 h; 42.8g of intermediate D, 1.3L of anhydrous methanol and 2.8g of sodium methoxide were added to the reaction flask, and the reaction was stirred at 25 ° C for3 h. The reaction was quenched by adding 3.0 g of glacial acetic acid, and the filtrate was stirred and lysed at 0 ° C for 6 h. 8.1 g of an off-white solid were obtained in a yield of42.1percent.The relevant substances were detected by HPLC: purity 98.7percent, maximum single impurity 0.51percent.
2.8 g at 20℃; for 12 h; [0054] To a trimethylsilyl derivative of 5-azacytosine (6.9 g) dissolved in methylene chloride (34 mL) 1-chioro-3,5-di (4-chlorobenzoyl)-2-deoxy-D-ribose (125 eq) were added and the solution was brought to a temperature of from 0° C. to 10° C. SnCl4 (0.8 eq) was added to the solution and the temperature was left raise up to the room value. At the end of the reaction, the mixture was cooled up to a temperature of from 0° C. to 20° C. and DMSO (4 eq) was slowly added. The precipitated SnCl4-DMSO complex was isolated by filtration. Sodium bicarbonate (4 eq) was added to the organic phase and the mixture was kept under stirring for 1 hout The solid was removed by filtration and the organic phase was washed with cold watet The organic phases were separated, dried over sodium sulfate and the solvent was removed by distillation under low pressure to give a viscous residue. The residue was added with methanol (70 mL) and a 30percent solution of sodium methoxide in methanol (0.2 eq) was added to the resultant solution. The solution was kept under stirring at room temperature for 12 hours and the resultant solid was filtered, washed with methanol (300 mL) and dried. 2.8 g of decitabine with a purity of 9 8.8percent (determined by HPLC) and a tin content lower than 200 ppm was obtained.
Reference: [1] Patent: EP2050757, 2009, A1, . Location in patent: Page/Page column 4
[2] Patent: CN108239128, 2018, A, . Location in patent: Paragraph 0108; 0112; 0113; 0114; 0115; 0120; 0127; 0136
[3] Patent: US2014/135490, 2014, A1, . Location in patent: Paragraph 0054
  • 4
  • [ 931-86-2 ]
  • [ 3601-89-6 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: EP2371825, 2011, A1, . Location in patent: Page/Page column 9
[2] Patent: US2011/245485, 2011, A1, . Location in patent: Page/Page column 7
  • 5
  • [ 931-86-2 ]
  • [ 21740-23-8 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: EP2048151, 2009, A1, . Location in patent: Page/Page column 3
  • 6
  • [ 1207459-15-1 ]
  • [ 52523-35-0 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: US2010/36112, 2010, A1, . Location in patent: Page/Page column 7-8
  • 7
  • [ 931-86-2 ]
  • [ 951-78-0 ]
  • [ 2353-33-5 ]
Reference: [1] Catalysis Today, 2016, vol. 259, p. 197 - 204
  • 8
  • [ 1034301-08-0 ]
  • [ 1140891-02-6 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: US2010/249394, 2010, A1, . Location in patent: Page/Page column 6
  • 9
  • [ 931-86-2 ]
  • [ 17039-17-7 ]
  • [ 2353-33-5 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2588 - 2601
  • 10
  • [ 22432-93-5 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: WO2010/129211, 2010, A2, . Location in patent: Page/Page column 28
  • 11
  • [ 135567-49-6 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: US2006/14949, 2006, A1, . Location in patent: Page/Page column 6; 15
[2] Patent: US2006/14949, 2006, A1, . Location in patent: Page/Page column 18
  • 12
  • [ 135567-49-6 ]
  • [ 2353-33-5 ]
Reference: [1] Patent: US2006/14949, 2006, A1, . Location in patent: Page/Page column 15
  • 13
  • [ 69304-64-9 ]
  • [ 2353-33-5 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1981, vol. 70, # 11, p. 1228 - 1232
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