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[ CAS No. 4985-92-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4985-92-6
Chemical Structure| 4985-92-6
Chemical Structure| 4985-92-6
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Product Citations

Nicholas O. Schneider ; Kendra Gilreath ; Daniel J. Burkett , et al. DOI:

Abstract: Glycogen synthase kinase-3 (GSK-3) is a serine/threonine kinase which plays a center role in the phosphorylation of a wide variety of proteins, generally leading to their inactivation. As such, GSK-3 is viewed as a therapeutic target. An ever-increasing number of small organic molecule inhibitors of GSK-3 have been reported. Phenylmethylene hydantoins are known to exhibit a wide range of inhibitory activities including for GSK-3β. A family of fourteen 2-heterocycle substituted methylene hydantoins (14, 17–29) were prepared and evaluated for the inhibition of GSK-3β at 25 μM. The IC50 values of five of these compounds was determined; the two best inhibitors are 5-[(4′-chloro-2-pyridinyl)methylene]hydantoin (IC50 = 2.14 ± 0.18 μM) and 5-[(6′-bromo-2-pyridinyl)methylene]hydantoin (IC50 = 3.39 ± 0.16 μM). The computational docking of the compounds with GSK-3β (pdb 1q41) revealed poses with hydrogen bonding to the backbone at Val135. The 5-[(heteroaryl)methylene]hydantoins did not strongly inhibit other metalloenzymes, demonstrating poor inhibitory activity against matrix metalloproteinase-12 at 25 μM and against human carbonic anhydrase at 200 μM, and were not inhibitors for Staphylococcus aureus pyruvate carboxylase at concentrations >1000 μM.

Keywords: nitrogen heterocycles ; glycogen synthase kinase 3β ; computational docking

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Product Details of [ 4985-92-6 ]

CAS No. :4985-92-6 MDL No. :MFCD07367942
Formula : C7H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :SARODJOLCPBJHK-UHFFFAOYSA-N
M.W : 121.14 Pubchem ID :10464339
Synonyms :

Calculated chemistry of [ 4985-92-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.59
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.16 mg/ml ; 0.0178 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 5.0 mg/ml ; 0.0413 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.589 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 4985-92-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4985-92-6 ]

* 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 [ 4985-92-6 ]
  • Downstream synthetic route of [ 4985-92-6 ]

[ 4985-92-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 3510-66-5 ]
  • [ 68-12-2 ]
  • [ 4985-92-6 ]
YieldReaction ConditionsOperation in experiment
39% With n-butyllithium In diethyl ether at -78℃; for 2 h; For the synthesis of 5-methylpyridin-2-carbaldehyde (B; n = 1 ; R1 , R2, R4 = H; R3 = Me) 50 g (290 mmol) 2-bromo-5-methylpyridinβ (B2; R1, R2, R4 = H; R3 = Me) was dissolved in 2500 ml diethylether and cooled to -78°C. Then, 150 ml (380 mmoi) nBuLi was added drop wise and the reaction mixture was stirred for 2hrs at -78° C. DMF (31.5 ml, 407 mmol) was added drop wise and after the reaction mixture was allowed to warm to room temperature, water was added to the reaction mixture. Both, organic and aqueous layer were separated and the water layer was extracted with ethyl acetate for three times. All organic layers were combined, washed with brine, dried over Na2SO4 and the solvent was evaporated in vacuo yielding a brown oil. This residue was purified by flash chromatography with heptane (supplemented with ethyl acetate from 0 to 25percent). Yield: 19 g (39percent) brown solid.MS (APCI): m/z 122 (M+1)+. 1H NMR (CDCI3, 360 MHz) δ (ppm): 2.48 (s, 3H, CH3); 7.70 (dd, J=7.9 Hz1 2.0 Hz, 1H, pyridine H4); 7.91 (d, J=7.7 Hz1 1H, pyridine H3); 8.68 (s, 1H, pyridine H6); 10.10 (s, 1H, aldehyde).
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 8, p. 2238 - 2243[2] Angew. Chem., 2018, vol. 130, # 8, p. 2260 - 2265,6
[3] Patent: WO2009/60030, 2009, A1, . Location in patent: Page/Page column 38-39
[4] Chemistry - A European Journal, 2008, vol. 14, # 17, p. 5313 - 5328
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6763 - 6770
  • 2
  • [ 3430-13-5 ]
  • [ 68-12-2 ]
  • [ 4985-92-6 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;
Stage #2: for 0.5 h;
Intermediate 161 : 5-methyl-2-pyridinecarbaldehvde; 5 g of 5-bromo-2-methylpyridine (29.1 mmole, Aldrich), dissolved in 60 mL of dry THF.The solution was cooled to -780C. To this solution, were added 15.99 mL of BuLi (32.0 mmole) and the reaction mixture was stirred at -780C for 0.5 h. Then 4.50 mL of dry DMF <n="175"/>(58.1 mmole) were added and stirring was continued for 0.5 h. 30 mL of water were added followed by 100 mL of AcOEt. The organic layer was separated, dried over Na2SO4, filtered and evaporated under vacuum to give a crude that was purified on Isco- Companion (CH/AcOEt 1 :1 to 1 :9) to give the title compound as a yellow oil (1.6 g, 45percent yield). 1H-NMR (400 MHz, CDCI3): δ 1.99 (s, 3H), 7.22 (d, 1 H), 7.43 (d, 1 H), 8.16 (s, 1 H), 9.59 (s, 1 H); m/z (ES): 121.99 [M+H]+.
Reference: [1] Patent: WO2008/148853, 2008, A1, . Location in patent: Page/Page column 172-173
  • 3
  • [ 661458-29-3 ]
  • [ 68-12-2 ]
  • [ 4985-92-6 ]
YieldReaction ConditionsOperation in experiment
62.6% at 20℃; for 0.166667 h; To the 0.25 M 5-methyl-2-pyridinylmagnesium bromide of THF solution (20 mL, 5 [MMOL),] DMF (0.773 mL, 10 mmol) was added at room temperature under argon. The reaction mixture was stirred for 10 min. and concentrated in vacuo. The residue was quenched with saturated ammonium chloride and dichloromethane. The organic layer was dried and the product was purified by silica gel column chromatography with 20 percent ethyl acetate in hexanes to give 379 mg (62.6percent) of the title compound. GC-MS [(M+)] : 121.
Reference: [1] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 41
  • 4
  • [ 55876-82-9 ]
  • [ 4985-92-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 3026 - 3032
[2] Patent: US2018/79742, 2018, A1,
  • 5
  • [ 22940-71-2 ]
  • [ 4985-92-6 ]
YieldReaction ConditionsOperation in experiment
25% With manganese(IV) oxide In chloroform at 50℃; To a solution of 41 (5-methylpyridin-2-yl)methanol [Example 2, Step 2] (2 g, 16.24 mmol, 1.00 equiv) in 42 chloroform (25 mL) was added 43 MnO2 (18.39 g, 211.53 mmol, 13.00 equiv). The mixture was stirred overnight at 50° C. The solids were filtered out. The filtrate was concentrated under vacuum to afford 500 mg (25percent) of 44 5-methylpyridine-2-carbaldehyde as brown oil. LC-MS: m/z=122[M+H]+
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 29, p. 9795 - 9798
[2] Patent: US2018/79742, 2018, A1, . Location in patent: Paragraph 0326; 0327
[3] Yakugaku Zasshi, 1958, vol. 78, p. 661,665[4] Chem.Abstr., 1958, p. 18399
  • 6
  • [ 1620-77-5 ]
  • [ 4985-92-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 3026 - 3032
[2] Patent: US2018/79742, 2018, A1,
  • 7
  • [ 1121-60-4 ]
  • [ 4985-92-6 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 19, p. 9805 - 9815
  • 8
  • [ 589-93-5 ]
  • [ 4985-92-6 ]
Reference: [1] Chemische Berichte, 1957, vol. 90, p. 758,761
  • 9
  • [ 772-71-4 ]
  • [ 4985-92-6 ]
Reference: [1] Yakugaku Zasshi, 1958, vol. 78, p. 661,665[2] Chem.Abstr., 1958, p. 18399
  • 10
  • [ 4986-05-4 ]
  • [ 4985-92-6 ]
Reference: [1] Yakugaku Zasshi, 1958, vol. 78, p. 661,665[2] Chem.Abstr., 1958, p. 18399
  • 11
  • [ 4985-92-6 ]
  • [ 4434-13-3 ]
Reference: [1] Yakugaku Zasshi, 1958, vol. 78, p. 661,665[2] Chem.Abstr., 1958, p. 18399
  • 12
  • [ 4985-92-6 ]
  • [ 31181-90-5 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 19, p. 9805 - 9815
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