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Chemical Structure| 171364-78-6 Chemical Structure| 171364-78-6

Structure of 171364-78-6

Chemical Structure| 171364-78-6

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Product Citations

Product Citations

Smolkova, Denisa ; Gregus, Michal ; Cmelik, Richard ; Pizova, Hana ; Jansen-van Vuuren, Ross D ; Bobal, Pavel , et al.

Abstract: This work focuses on profiling N-linked glycans by capillary electrophoresis coupled to mass spectrometry using a novel fluorescent and mass spectrometry (MS) active derivatization tag. The label is based on 2-phenylpyridine bearing tertiary amine and hydrazide functionalities. It provides efficient labeling via hydrazone formation chemistry, promising fluorescence properties, and ionization efficiency in the positive ion MS mode. Electrophoretic analysis in a neutral-coated capillary allowed baseline separation of maltooligosaccharides with limits of detection in nanomolar concentrations. The developed labeling method was successfully applied to the analyses of N-linked glycans released from several glycoproteins such as bovine ribonuclease B, human immunoglobulin G, or chicken albumin.

Keywords: Oligosaccharides ; Glycans ; Labeling ; Phenylpyridine ; Capillary electrophoresis ; Mass spectrometry

Purchased from AmBeed: ; ;

Alternative Products

Product Details of [ 171364-78-6 ]

CAS No. :171364-78-6
Formula : C14H22BNO2
M.W : 247.14
SMILES Code : CN(C)C1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1
MDL No. :MFCD05663854
InChI Key :DGMLJJIUOFKPKB-UHFFFAOYSA-N
Pubchem ID :2758659

Safety of [ 171364-78-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317
Precautionary Statements:P261-P280

Computational Chemistry of [ 171364-78-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 6
Fraction Csp3 0.57
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 77.12
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

21.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.03
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.05
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.67
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.64

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.4
Solubility 0.0993 mg/ml ; 0.000402 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.15
Solubility 0.175 mg/ml ; 0.000706 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.11
Solubility 0.0191 mg/ml ; 0.0000771 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.66 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.96

Application In Synthesis of [ 171364-78-6 ]

* 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.

  • Downstream synthetic route of [ 171364-78-6 ]

[ 171364-78-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 171364-78-6 ]
  • [ 1202-25-1 ]
  • 2
  • [ 19063-55-9 ]
  • [ 171364-78-6 ]
  • [ 1337936-09-0 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 80℃; for 8h;Inert atmosphere; It mainly includes the following steps: taking the coumarin derivative (500 mg, 2.2 mmol) after bromination at the 6 position,N,N-dimethylbenzene derivative (618 mg, 2.5 mmol) and K2CO3 (133 mg), which are introduced para-borate borate.The solution was dissolved in a toluene-ethanol mixed solution (3:1, 80 ml).After passing nitrogen gas for 30 min, 15 mg of tetrakistriphenylphosphine palladium catalyst was added to the solvent, and the mixture was heated to 80 C, 1000 r / min, and reacted for 8 hours.After the reaction, it was cooled to room temperature, washed with a large amount of water and extracted with dichloromethane.After removing excess solvent by a rotary evaporator, 100 mL of a dichloromethane solution was added to dissolve the solid, washed with 40 mL of distilled water, and separated.The remaining water was removed with anhydrous sodium sulfate, separated, and dried.The crude product was separated and purified on a 200-300 mesh silica gel column using dichloromethane-n-hexane (volume ratio 2:5) as eluent to afford yellow compound A as shown in Fig. 2.The coumarin-type organic nonlinear optical material compound A obtained by the above production method had a yield of 60%.
  • 3
  • [ 22034-13-5 ]
  • [ 171364-78-6 ]
  • 4-(benzo[c][1,2,5]thiadiazol-4-yl)-N,N-dimethylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 80℃; for 12h;Inert atmosphere; To a solution of 4-bromobenzo[c] [1,2,5]thiadiazole (107 mg,0.50 mmol) and N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (124 mg, 0.50 mmol) in toluene-ethanol(30 mL/10 mL), Pd(PPh3)4 (57 mg, 0.05 mmol) and anhydrous K2CO3 (207 mg, 1.5 mmol) were added under an argon flow at room temperature. The mixturewas then heated to 80 °C for12 h. The mixture was quenched with water after cooling back to room temperature and extracted with dichloromethane. The combined extract was dried with anhydrous Na2SO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with CH2Cl2/petroleum (1:1) to afford NBT as an orange solid. Yield: 49percent. m.p. 128-129 °C. FT-IR (KBr, upsilon/cm-1): 3052.9, 2883.6, 2801.4, 1605.9, 1519.6, 1480.6, 1441.3,1357.3, 1230.9, 1204.9, 1119.8, 1066.0, 948.4, 893.2, 849.0, 825.1, 800.2, 748.4. 1H NMR (CDCl3, 400 MHz): 7.88 (d, J 8.4 Hz, 3H), 7.62(d, J 8.0 Hz, 2H), 6.88 (d, J 8.0 Hz, 2H), 3.03 (s, 6H); 13C NMR (CDCl3, 100 MHz): delta 155.92, 153.86, 150.68, 134.81, 130.17, 129.94, 125.95, 125.34, 119.03, 112.43, 40.54. HRMS (EI mode) (m/z): found(M) 255.0827; calcd for C14H13N3S: 255.0830.
  • 5
  • [ 1753-75-9 ]
  • [ 171364-78-6 ]
  • 5-(4-dimethylaminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
 

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Technical Information

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