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[ CAS No. 487021-52-3 ] {[proInfo.proName]}

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Chemical Structure| 487021-52-3
Chemical Structure| 487021-52-3
Structure of 487021-52-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 487021-52-3 ]

CAS No. :487021-52-3 MDL No. :MFCD08277040
Formula : C12H12N4O4S Boiling Point : -
Linear Structure Formula :- InChI Key :YAEMHJKFIIIULI-UHFFFAOYSA-N
M.W : 308.31 Pubchem ID :448014
Synonyms :
GSK 3β inhibitor VIII;AR 0133418;GSK-3beta Inhibitor VIII.;AR-AO-14418;SN 4521;Glycogen Synthase Kinase 3β Inhibitor VIII;AR 014418
Chemical Name :1-(4-Methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea

Calculated chemistry of [ 487021-52-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.17
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.42
TPSA : 137.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.04
Log Po/w (MLOGP) : -0.29
Log Po/w (SILICOS-IT) : 0.17
Consensus Log Po/w : 1.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.31
Solubility : 0.151 mg/ml ; 0.000491 mol/l
Class : Soluble
Log S (Ali) : -5.12
Solubility : 0.00233 mg/ml ; 0.00000754 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.0533 mg/ml ; 0.000173 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.94

Safety of [ 487021-52-3 ]

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 [ 487021-52-3 ]

* 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.

  • Downstream synthetic route of [ 487021-52-3 ]

[ 487021-52-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 121-66-4 ]
  • [ 56651-60-6 ]
  • N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran; hexane at 20℃; 1.) Synthesis of the urea derivatives General Procedure: To the residue was added dry tetrahydrofuran (THF, 1.5 ml). It was added dropwise to a solution of n-buthyllithium (0.80 mmol, 1.6 M in n-Hexane) deprotonated amine (0.80 mmol) in 1.5 ml tetrahydrofuran and stirred at room temperature overnight. The reaction solution was added to a vigorous stirred water to give the solid crude urea. The solid was filtered off and recrystallised from methanol or ethanol.
  • 2
  • [ 2393-23-9 ]
  • [ 487021-52-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / dichloromethane; water / 2.5 h / 0 °C 2: n-butyllithium / tetrahydrofuran; hexane / 20 °C
Multi-step reaction with 2 steps 1.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 20 °C 1.2: 20 °C / Inert atmosphere 2.1: sodium hydride / 20 °C
  • 3
  • [ 121-66-4 ]
  • [ 149047-29-0 ]
  • [ 487021-52-3 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 20h; Inert atmosphere;
47.2% With sodium hydride at 20℃; 4.2.3 Synthesis of compounds 5a-5n General procedure: General method C: To a solution of compound 4 or 6 in DMF was added compound 2 (1eq) and NaH (1.2eq). After stirring for 8-10h at room temperature. The reaction mixture was diluted with AcOEt and brine. The aqueous layer was extracted with AcOEt, and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography to give the desired compound as a solid.
  • 4
  • [ 121-66-4 ]
  • [ 32315-10-9 ]
  • [ 2393-23-9 ]
  • [ 487021-52-3 ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: bis(trichloromethyl) carbonate; 4-methoxy-benzylamine With triethylamine In dichloromethane at 0 - 20℃; for 1.25h; Inert atmosphere; Stage #2: 2-amino-5-nitro-1,3-thiazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; 1 Procedure A: urea formation with triphosgene General procedure: A solution of triphosgene (0.4 mmol) in dry CH2C12 (2.5 mL) was prepared underargon atmosphere in a dry round bottom flask and cooled to 0 °C. A solution of amine (1.0 mmol) and triethylamine (2.2 - 3.2 mmol) in dry CH2C12 (1.9 mL) which wasprepared under argon atmosphere in a dry round bottom flask was added dropwise to the first solution. The ice bath was removed after 15 minutes and the reaction mixture was stilTed for 1 h at room temperature. In another round bottom flask under argon, triethylamine (1.1 mmol) was added to a solution of thiazole (1.1 mmol) in dry DMF (1.3 mL). This solution was cooled to 0°C and the isocyanate solution was added. The redreaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel column (CH2C12/MeOH 10:0 to 95:5 (v/v) in 30 mm) to afford an oil or a solid, which was triturated in hexanes and CH2C12 and filtered to afford the urea.Obtained according to general procedure A from 4-methoxybenzylamine and2-amino-5-nitrothiazole. Pale yellow solid (0.124 g, 25%). Purity = 100%;tr = 2.50 mm; MS (ESI-): m/z = 307 [M-H1-; HRMS m/z calculated for C12H11N4045 [M-H1- 307.0506, found 307.0507. 1H NMR (DMSO-d6) ö (ppm): 11.7(br s, 1H), 8.52 (s, 1H), 7.37-7.25 (m, 6H), 4.38 (d, 1H, J = 7.5 Hz). 13C NMR (DMSOd 6) ö (ppm): 164.8, 158.9, 153.8, 143.9, 141.4, 131.2, 129.2, 114.3, 55.5, 43.1.
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