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[ CAS No. 96-50-4 ] {[proInfo.proName]}

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Chemical Structure| 96-50-4
Chemical Structure| 96-50-4
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Quality Control of [ 96-50-4 ]

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Product Citations

Product Citations      Expand+

Huffman, Samantha E. ; Yawson, Gideon K. ; Fisher, Samuel S. , et al. DOI: PubMed ID:

Abstract: Metal-based therapeutics are uniquely suited to target soluble Aβ and have shown considerable promise to prevent the aggregation and induced cytotoxicity of the peptide in vitro. Herein, we have prepared a small series of derivatives of two promising Ru(III) complexes NAMI-A (imidazolium [trans-RuCl4(1H-imidazole)(DMSO-S)]) and PMRU20 (2-aminothiazolium [trans-RuCl4(2-aminothiazole)2]), to determine structure-activity relationships (SAR) for Ru(III) therapeutics for Alzheimer's Disease. Using the three complementary methods of Thioflavin T fluorescence, dynamic light scattering (DLS), and transmission electron microscopy (TEM), it was determined that the symmetry around the metal center did not significantly impact the activity of the complexes, but rather the attached thiazole ligand(s) mitigated Aβ aggregation. Across both families of Ru(III) complexes the determined SAR for the functional groups on the thiazole ligands to modulate Aβ aggregation were NH2 > CH3 > H. These results highlight the importance of secondary interactions between the metallotherapeutic and the Aβ peptide where hydrogen-bonding has the greatest impact on modulating Aβ aggregation.

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Yawson, Gideon Kweku ;

Abstract: Alzheimer’s disease (AD) is characterized by the observation of protein deposits comprised primarily of the peptide amyloid-beta (Aβ) which leads to physical changes within the brain and eventually death of an AD patient. The full-length Aβ peptide (amino acids 1-42) contains 3 histidine residues that have shown an affinity towards endogenous metal ions, a phenomenon that is exploited by metal-based drugs. Recently, two ruthenium(III) complexes NAMI-A (imidazolium [trans-RuCl4(1H-imidazole)(DMSO-S)]) and PMru20 (2-aminothiazolium [transRuCl4(2-aminothiazole)2]) were subjected to Aβ aggregation inhibition studies. Whilst it was interesting to find that both NAMI-A and PMru20 modulated Aβ aggregation, crucial questions regarding their observed activities persisted, specifically the structure-activity relationship (SAR) for the compounds. Therefore, azole-based derivatives of both complexes were prepared to determine the SAR for Ru(III) complexes to modulate the aggregation of Aβ. Analysis of the prepared Ru(III) was facilitated by three complementary methods: fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. Altogether, the results of this study have highlighted the importance of hydrogen bonding functional groups on the azole ligands having the most prominent impact on Aβ aggregation.

Keywords: Alzheimer’s Disease ; Ruthenium ; PMru20 ; NAMI-A ; Azole ; Thioflavin T ; DLS

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Product Details of [ 96-50-4 ]

CAS No. :96-50-4 MDL No. :MFCD00005325
Formula : C3H4N2S Boiling Point : -
Linear Structure Formula :- InChI Key :RAIPHJJURHTUIC-UHFFFAOYSA-N
M.W : 100.14 Pubchem ID :2155
Synonyms :
2-Aminothiazole;2-Thiazolylamine;NSC 1900;Basedol
Chemical Name :Thiazol-2-amine

Calculated chemistry of [ 96-50-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.52
TPSA : 67.15 ?2

Pharmacokinetics

GI absorption : High
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) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : 0.38
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : -0.65
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.32
Solubility : 4.83 mg/ml ; 0.0482 mol/l
Class : Very soluble
Log S (Ali) : -1.36
Solubility : 4.42 mg/ml ; 0.0441 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.86
Solubility : 14.0 mg/ml ; 0.139 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 96-50-4 ]

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

Application In Synthesis of [ 96-50-4 ]

* 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 [ 96-50-4 ]

[ 96-50-4 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 96-50-4 ]
  • [ 3034-48-8 ]
  • 2
  • [ 96-50-4 ]
  • [ 51991-94-7 ]
  • [ 106695-67-4 ]
  • 3
  • [ 96-50-4 ]
  • [ 1186-73-8 ]
  • [ 224313-88-6 ]
  • 4
  • [ 96-50-4 ]
  • [ 1186-73-8 ]
  • N6-(1,3-thiazol-2-yl)-7-hydroxy-5-oxo-5H-<1,3>thiazolo<3,2-a>pyrimidinecarboxamide [ No CAS ]
  • 5
  • [ 96-50-4 ]
  • [ 7697-25-8 ]
  • 8-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one [ No CAS ]
  • 6
  • [ 96-50-4 ]
  • [ 17823-69-7 ]
  • [ 1027818-48-9 ]
  • 7
  • [ 96-50-4 ]
  • [ 33985-71-6 ]
  • [ 119072-55-8 ]
  • N-(tert-butyl)-6-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)imidazo[2,1-b]thiazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In toluene; at 100℃; for 0.166667h;Microwave irradiation; Sealed tube; General procedure: General Procedure (GP): In a MW sealed-tube equipped with a magnetic stirring bar, to a 0.5 M solution of aldehyde (1.0 equiv.) in anhydrous toluene [0.5 M], amine (1.0 equiv.) and isocyanide (1.0 equiv.) were added sequentially and the reaction mixture was MW-heated (100 oC,150 W) for 10 minutes. Then, the solvent was removed until dryness and the crude was immediately purified by silica-gel column chromatography using a mixture of hexanes with ethyl acetate (7/3; v/v) to afford the corresponding products 1a-w.
  • 8
  • [ 96-50-4 ]
  • [ 931-53-3 ]
  • [ 33985-71-6 ]
  • N-cyclohexyl-6-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)imidazo[2,1-b]thiazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In toluene; at 100℃; for 0.166667h;Microwave irradiation; Sealed tube; General procedure: General Procedure (GP): In a MW sealed-tube equipped with a magnetic stirring bar, to a 0.5 M solution of aldehyde (1.0 equiv.) in anhydrous toluene [0.5 M], amine (1.0 equiv.) and isocyanide (1.0 equiv.) were added sequentially and the reaction mixture was MW-heated (100 oC,150 W) for 10 minutes. Then, the solvent was removed until dryness and the crude was immediately purified by silica-gel column chromatography using a mixture of hexanes with ethyl acetate (7/3; v/v) to afford the corresponding products 1a-w.
  • 9
  • [ 96-50-4 ]
  • [ 41360-32-1 ]
  • C11H10N2O4S2 [ No CAS ]
  • 10
  • [ 96-50-4 ]
  • [ 99368-67-9 ]
  • N-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)thiazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 3.0h;Inert atmosphere; To a stirred solution of <strong>[99368-67-9]2-chloro-5-nitro-3-(trifluoromethyl)pyridine</strong> (2.0 g, 8.83 mmol) in 1,4-dioxane (20 mL) was added, cesiu m carbonate (5.75 g, 17.66 mmol) and the contents were purged with nitrogen for 30 min followed by sequential addition of thiazol-2-amine (1.32 g, 13.24 mmol), xantphos (0.511 g, 0.883 mmol) and Pd2(dba)3 (0.808 g, 0.883 mmol). The resulting reaction mixture was heated at 100eC for 3 h. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 0.850 g (33percent) of the titled product as a colorless gum. 1HNMR (400 MHz, DMSO-d6) U13.32 (s, 1H), 9.32 (d, J = 2.7 Hz, 1H), 8.50 (d, J = 2.7 Hz, 1H), 7.50 (d, J = 4.6 Hz, 1H), 7.12 (d, J = 4.6 Hz, 1H); ESI-MS (m/z) 291.21 (MH)\
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