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Chemical Structure| 34160-40-2 Chemical Structure| 34160-40-2
Chemical Structure| 34160-40-2

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Product Citations

Nicholas O. Schneider ; Kendra Gilreath ; Daniel J. Burkett ; Martin St. Maurice ; William A. Donaldson ;

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

Alternative Products

Product Details of 6-Bromo-2-pyridinecarboxaldehyde

CAS No. :34160-40-2
Formula : C6H4BrNO
M.W : 186.01
SMILES Code : C1=CC=C(Br)N=C1C=O
MDL No. :MFCD02683546
InChI Key :QWFHFNGMCPMOCD-UHFFFAOYSA-N
Pubchem ID :2757009

Safety of 6-Bromo-2-pyridinecarboxaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 6-Bromo-2-pyridinecarboxaldehyde

* 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 [ 34160-40-2 ]

[ 34160-40-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 34160-40-2 ]
  • [ 128733-85-7 ]
  • [ 866613-68-5 ]
  • 2
  • [ 34160-40-2 ]
  • [ 103291-07-2 ]
  • [ 1357564-25-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of <strong>[103291-07-2]5-bromo-2-fluoroanisole</strong> (200 mg, 0.98 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (24 mg, 0.98 mmol, 1 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After reaching room temperature, 6-bromopyridin-2-yl carboxaldehyde (182 mg, 0.98 mmol, 1 equiv) was added and the reaction mixture was heated to 80 C and stirred overnight at 80 C. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was used in the next step without further purification. C13H11BrFNO2; MW 312.
  • 3
  • [ 34160-40-2 ]
  • [ 57002-01-4 ]
  • [ 1448433-79-1 ]
YieldReaction ConditionsOperation in experiment
90% With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere; Step 1 : To an argon saturated mixture of <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> (8) (2.74 g, 16.0 mmol), 6-bromopicolinaldehyde (9) (3.0 g, 16 mmol), Pd(OAc)2 (0.04 g, 0.18 mmol), K2C03 (2M in z-PrOH, 30 mmol) was added PPh3 (0.20 g, 0.76 mmol). The reaction mixture was stirred at 70 C for 20 hours under N2, concentrated under reduced pressure and partitioned between H20 (80 ml) and ethyl acetate (80 ml). Organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash chromatography (30% - 50% EtOAc - hexanes gradient) gave alkene (10) as a pale yellow oil. Yield (3.1 g, 90%); 1H NMR (400 MHz, DMSO-d6) delta 9.34 (s, 1H), 7.93 (t, J= 7.6 Hz, 1H), 7.71 (d, J= 8.4 Hz, 1H), 7.69 (d, J= 8.4 Hz, 1H), 7.86 (dd, J= 6.8, 16.0 Hz, 1H), 6.54 (d, J= 16 Hz, 1H), 2.26-2.16 (m, 1H), 1.84-1.58 (m, 5H), 1.36-1.10 (m, 5H).
90% With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere; £6L ?(RI ?5) tE6 2 (9p-oswu ?ZRN oot) WIN RT (%o6? FE) PJaA MOJJa( ajUd U SU (01) auajj AU QuatpU1SauUxaJ-oyQ3 %oc-%oE) £qdU1OwwO1qo JSU £q uot-Uogun alnSSald paonpai iapun pawauaouoo UU tOStUNSflO1p(quU laAo paup SUM IaJ(UJ otUU1Q Qw os) arnaop(a UU (jw os) OtR uaaaq pauotpnUd puU alnSSaldpaonpai iapun papmuaouoo tN iapun Srnoq o IOJ D00L U 1fl3S SUM ainjxnu uOl3oUal aj Qowm 9L0 ? oo) Eq SUM (jounu OE ?R01d1 U? w) EQy ?Qoanu810 ? too) t(vo)Pd ?Qoww 91 ? oE) (6) ap(qapJUutJ-OotdOwOlq-9 ?Qoanu 091 ? tLi (5) ptcrn otuOlOqQi(utAp(-xajopi(o-j-() jo ainpctw PW1flJUS UO1U UU oi :1 dais(Rd ?m) 0IU9EI ?(Rd ?w) SdI-tSI ?(RI ?w) 9I9 ?(RI ?ZR 91=1 ?P) td9 ?(RI ?ZR 091 ?89=f ?PP) 98L ?(RI ?ZR T8=1 ?P) 69L ?(RI ?ZR T8=1 ?P) ILL ?(RI ?ZR 9L=f ?1)
  • 4
  • [ 34160-40-2 ]
  • [ 1509929-21-8 ]
  • 5
  • [ 34160-40-2 ]
  • [ 1240041-69-3 ]
  • [ 857064-38-1 ]
 

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