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[ CAS No. 195062-57-8 ] {[proInfo.proName]}

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Chemical Structure| 195062-57-8
Chemical Structure| 195062-57-8
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Product Citations

Product Citations

Paul Getreuer ; Laura Marretta ; Emine Toyoglu , et al. DOI:

Abstract: In this contribution we report the synthesis, characterization and in vitro anticancer activity of novel cyclometalated 4-phenylthiazole-derived ruthenium(II) (2a–e) and osmium(II) (3a–e) complexes. Formation and sufficient purity of the complexes were unambigiously confirmed by 1H-, 13C- and 2D-NMR techniques, X-ray diffractometry, HRMS and elemental analysis. The binding preferences of these cyclometalates to selected amino acids and to DNA models including G-quadruplex structures were analyzed. Additionally, their stability and behaviour in aqueous solutions was determined by UV-Vis spectroscopy. Their cellular accumulation, their ability of inducing apoptosis, as well as their interference in the cell cycle were studied in SW480 colon cancer cells. The anticancer potencies were investigated in three human cancer cell lines and revealed IC50 values in the low micromolar range, in contrast to the biologically inactive ligands.

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Product Details of [ 195062-57-8 ]

CAS No. :195062-57-8 MDL No. :MFCD03453662
Formula : C13H19BO2 Boiling Point : -
Linear Structure Formula :CH3C6H4B(OC(CH3)2C(CH3)2O) InChI Key :GKSSEDDAXXEPCP-UHFFFAOYSA-N
M.W : 218.10 Pubchem ID :2774016
Synonyms :

Calculated chemistry of [ 195062-57-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.88
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.33
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.46
Solubility : 0.075 mg/ml ; 0.000344 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.102 mg/ml ; 0.000465 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.39
Solubility : 0.00886 mg/ml ; 0.0000406 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.82

Safety of [ 195062-57-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 195062-57-8 ]

* 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 [ 195062-57-8 ]
  • Downstream synthetic route of [ 195062-57-8 ]

[ 195062-57-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 120-92-3 ]
  • [ 195062-57-8 ]
  • [ 1671-77-8 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 16, p. 5347 - 5351
  • 2
  • [ 195062-57-8 ]
  • [ 128376-64-7 ]
YieldReaction ConditionsOperation in experiment
84% With N-Bromosuccinimide; dibenzoyl peroxide In 1,4-dioxane; water for 12 h; Inert atmosphere; Reflux Operation is the same as in Example 1, and the feed is as follows:21.8 g (0.1 mol) of p-methylphenylboronic acid pinacol ester, 39.2 g (0.22 mol) of N-bromosuccinimide,150 ml of dioxane and 0.5 g (0.002 mol) of benzoyl peroxide.The obtained product was 19.5 g of p-formylphenylboronic acid pinacol ester with a yield of 84percent. The analysis data is shown in Example 1.
In a 500 ml three-necked flask with mechanical stirring, a nitrogen inlet and a reflux condenser, 21.8 g (0.1 mol) p-methylphenylboronic acid pinacol ester were successively added.35.6 g (0.2 mol) of N-bromosuccinimide, 150 ml of dioxane and 0.24 g (0.001 mol) of benzoyl peroxide, and then heated to reflux under nitrogen protection until the sterol esters of p-methylphenylboronic acid disappeared. Then 150 ml of water was added and the mixture was heated and refluxed for 12 hours.Into a distillation apparatus, most of the solvent was distilled off, the residue was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate.Filtration, adding petroleum ether to cloud point, standing at low temperature (0-5°C), filtering and precipitating the product, yielding 16.5 g of p-formylphenylboronic acid pinacol ester in a yield of 71percent.
Reference: [1] Patent: CN107903280, 2018, A, . Location in patent: Paragraph 0040-0064
  • 3
  • [ 195062-57-8 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
82% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 12 h; Reflux Scheme 1. Synthesis of 4-(4,4,5,5-tetrarnethyl- 1,3,2 -dioxaboratophenyl)-methyl triphenylphosphonium bromide 4. [00120] Compound 6 (8) was prepared starting from 4,4,5,5-tetramethyl-2-p-tolyl- 1 ,2>,2- dioxaborolane 7, NBS and A1BN in carbon tetrachloride were refluxed for 12 hours. In an initial attempt 4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 4 was isolated as a white solid in 92percent yield. The minor excess of PPh3 was removed from the product by trituration with ether 2-3 times and the product was found to be stable under normal atmospheric conditions. Subsequently, the Wittig reaction of the ylide derived from this salt using benzaldehyde (Scheme 2) was optimized.
Reference: [1] Synlett, 2006, # 3, p. 475 - 477
[2] Patent: WO2006/81807, 2006, A2, . Location in patent: Page/Page column 20; 32
[3] Tetrahedron Letters, 2009, vol. 50, # 25, p. 3031 - 3034
[4] Tetrahedron Letters, 2012, vol. 53, # 11, p. 1316 - 1318
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5638 - 5641
[6] Patent: WO2012/112670, 2012, A1, . Location in patent: Page/Page column 31-32
[7] Journal of Organometallic Chemistry, 2015, vol. 798, p. 51 - 59
[8] Journal of the American Chemical Society, 2017, vol. 139, # 29, p. 10157 - 10163
[9] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6324 - 6328[10] Angew. Chem., 2018, vol. 130, p. 6432 - 6436,5
[11] Chemistry - A European Journal, 2009, vol. 15, # 46, p. 12627 - 12635
[12] Tetrahedron Letters, 2010, vol. 51, # 30, p. 3913 - 3917
[13] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[14] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 1, p. 59 - 62
[15] Patent: WO2017/8743, 2017, A1, . Location in patent: Paragraph 112
[16] Patent: US6335451, 2002, B1, . Location in patent: Page column 36
  • 4
  • [ 128-08-5 ]
  • [ 195062-57-8 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
76.1% With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 14 h; Reflux P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol),Bromosuccinimide (NBS, 9.91 g, 55.0 mmol),Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column,4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1percent) was isolated.
Reference: [1] Patent: CN107417714, 2017, A, . Location in patent: Paragraph 0056; 0057; 0061
[2] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
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