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[ CAS No. 500-22-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Type HazMat fee for 500 gram (Estimated)
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Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 500-22-1
Chemical Structure| 500-22-1
Structure of 500-22-1 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

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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Morse, Jared ; Ofodum, Nnamdi ; Tang, Fung-Kit , et al. DOI:

Abstract: Chloride is the most abundant anion in cell physiology and plays many critical roles in maintaining cellular homeostasis. However, current chloride sensors are rare, with inherent sensitivity in their emission properties, such as vulnerability to pH changes or short emission lifetimes. These limitations restrict theirapplication in aqueous media and imaging. In this work, we employed a transition metal complex bearing pyridinium as a recognition unit for chloride and studied the phosphorescence emission properties. Iridium(III) complex 1 was synthesized as an alternative chloride-sensitive luminophore. The conjugable design also allows customization for desired applications. Complex 1 exhibited high sensitivity and selectivity in chloride sensing across different physiological environments, regardless of pH fluctuation and ionic strength. Additionally, complex 1 featured a long microsecond emission lifetime. The chloride sensing ability of complex 1 can be measured through both luminescence intensity and long-lived phosphorescent lifetime simultaneously, providing an alternative potential route for chloride imaging.

Keywords: Chloride ; chloride detection ; chloride-sensitive luminophore ; iridium complex

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Product Details of [ 500-22-1 ]

CAS No. :500-22-1 MDL No. :MFCD00006382
Formula : C6H5NO Boiling Point : -
Linear Structure Formula :C5H4N(CHO) InChI Key :QJZUKDFHGGYHMC-UHFFFAOYSA-N
M.W : 107.11 Pubchem ID :10371
Synonyms :

Calculated chemistry of [ 500-22-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.62
TPSA : 29.96 ?2

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) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.29
Log Po/w (WLOGP) : 0.89
Log Po/w (MLOGP) : -0.23
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.18
Solubility : 7.15 mg/ml ; 0.0667 mol/l
Class : Very soluble
Log S (Ali) : -0.48
Solubility : 35.4 mg/ml ; 0.33 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.91
Solubility : 1.33 mg/ml ; 0.0124 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 500-22-1 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338+P310-P333+P313-P370+P378-P403+P233-P403+P235-P405-P501 UN#:1989
Hazard Statements:H226-H302-H315-H317-H318-H335-H412 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 500-22-1 ]

* 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 [ 500-22-1 ]

[ 500-22-1 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 4314-66-3 ]
  • [ 500-22-1 ]
  • [ 3000-75-7 ]
  • 2
  • [ 500-22-1 ]
  • [ 1075-34-9 ]
  • 5-Bromo-2-methyl-3-(pyridin-3-ylmethyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylsilane; In methanol; dichloromethane; trifluoroacetic acid; PREPARATION 8 5-Bromo-2-methyl-3-(3-pyridylmethyl)-1H-indole A solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (J. Chem. Soc., 1428 (1965)) (2.0 g) and 3-pyridinecarboxaldehyde (1.02 g) in dry dichloromethane (20 ml) was added dropwise over 10 minutes to a stirred solution of triethylsilane(3.30 g) in trifluoroacetic acid (20 ml) at 0° C. The solution was stirred at 0° C. for 30 minutes and then evaporated under vacuum, keeping the temperature below 35° C. The residue was dissolved in dichloromethane, and the solution was washed with 2N sodium hydroxide, water and dried (MgSO4). The solution was evaporated and the residue was chromatographed on silica gel, using dichloromethane/methanol (50:1) as eluent. The product fractions were combined and evaporated, and the residue was crystallized from ether to give the title compound (2.15 g), m.p. 188°-190° C. Found: C,59.62; H,4.43; N,9.26. C15 H13 BrN2 requires: C,59.82; H,4.35; N,9.30percent.
  • 3
  • [ 500-22-1 ]
  • [ 85920-63-4 ]
  • [ 122889-11-6 ]
  • (S)-5-Benzyloxymethyl-3-[1-hydroxy-eth-(Z)-ylidene]-1-pyridin-3-ylmethyl-pyrrolidine-2,4-dione [ No CAS ]
  • 4
  • [ 500-22-1 ]
  • [ 57497-39-9 ]
  • [ 1001387-10-5 ]
  • 5
  • [ 500-22-1 ]
  • [ 119072-55-8 ]
  • [ 769-92-6 ]
  • [ 1072-84-0 ]
  • [ 1417699-82-1 ]
  • 6
  • [ 500-22-1 ]
  • [ 37718-11-9 ]
  • [ 119072-55-8 ]
  • [ 769-92-6 ]
  • [ 1417699-92-3 ]
  • 7
  • [ 500-22-1 ]
  • [ 119072-55-8 ]
  • [ 769-92-6 ]
  • [ 41716-18-1 ]
  • [ 1417700-02-7 ]
  • 8
  • [ 500-22-1 ]
  • [ 116668-47-4 ]
  • (3-py)-CH=N-C10H6-COOH [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% In methanol; at 75℃; for 12h;Autoclave; A 25?ml Teflon-lined autoclave containing 6-amino-2-naphthnoic acid (370?mg, 2?mmol), 3-pyridinecarboxaldehyde (210?mg, 2?mmol), and methanol (20?ml) was sealed and heated at 75?°C for 12?h, and then air-cooled slowly for 24?h. The resulting yellow crystals were filtered, and washed with methanol (10?ml?×?3) to give ligand (67percent yield). Anal. Calc. for C17H12N2O2: C, 73.90; H, 4.38; N, 10.14. Found: C 74.00; H 4.30; N 10.15percent.
  • 9
  • [ 500-22-1 ]
  • [ 1585-90-6 ]
  • [ 107-97-1 ]
  • 2-(2-hydroxyethyl)-5-methyl-4-(pyridin-3-yl)tetrahydropyrrolo-[3,4-c]pyrrole-1,3(2H,3aH)-dione [ No CAS ]
  • 11
  • [ 500-22-1 ]
  • [ 20876-36-2 ]
  • 5-(pyridin-3-ylmethylamino)indolin-2-one [ No CAS ]
  • 12
  • [ 500-22-1 ]
  • [ 37170-50-6 ]
  • [ 6938-06-3 ]
  • 13
  • [ 500-22-1 ]
  • [ 78364-55-3 ]
  • C13H9FN4S [ No CAS ]
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