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Chemical Structure| 492-98-8 Chemical Structure| 492-98-8

Structure of 492-98-8

Chemical Structure| 492-98-8

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Product Citations

Product Citations

Tobias W. Morris ; David L. Wisman ; Nassem U. Din ; Duy Le ; Talat S. Rahman ; Steven L. Tait

Abstract: The creation of single-site metal centers (SSMCs) through the formation of metal-organic coordination networks is an area of interest due to the proven ability of SSMCs to improve selectivity for heterogeneous catalysts. In order to better understand the reactivity potential for the SSMCs it is necessary to study the ligand-metal interaction in the metal-organic coordination networks. In the work reported here, we demonstrate the ability to tune the oxidation state of vanadium from II to IV through the tailoring of redox-active ligands. Using the N-heterocyclic ligands of bipyrimidine (BP), bispyrimidinyltetrazine (BMTZ), and biimidazole (BIM) complexed with metallic V, we have shown that the oxidation state of the V metal centers can be tuned to V(II) for BP, V(III) for BMTZ, and V(IV) for BIM. These redox-active ligands provide similar coordination environments when complexed into one dimensional chains but result in different oxidation states for the single-site metal center.

Keywords: Metal-organic coordination ; On-surface redox assembly ; Scanning tunneling microscopy ; Density functional calculations ; X-ray photoelectron spectroscopy ; Redox-active ligands ; Charge transfer ; Metals

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Alternative Products

Product Details of [ 492-98-8 ]

CAS No. :492-98-8
Formula : C6H6N4
M.W : 134.14
SMILES Code : C1(C2=NC=CN2)=NC=CN1
MDL No. :MFCD00047014
InChI Key :AZUHIVLOSAPWDM-UHFFFAOYSA-N
Pubchem ID :101463

Safety of [ 492-98-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 492-98-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 36.17
TPSA ?

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

57.36 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-0.23
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

-0.1
Log Po/w (WLOGP)?

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

0.8
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.

-0.96
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

1.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.26

Water Solubility

Log S (ESOL):?

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

-1.28
Solubility 7.0 mg/ml ; 0.0522 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.65
Solubility 29.9 mg/ml ; 0.223 mol/l
Class?

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

Very 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

-2.56
Solubility 0.372 mg/ml ; 0.00277 mol/l
Class?

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

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

No
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

No
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.

-7.19 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

1.0
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

0.0 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)

1.56

Application In Synthesis of [ 492-98-8 ]

* 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.

  • Downstream synthetic route of [ 492-98-8 ]

[ 492-98-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 492-98-8 ]
  • [ 129013-83-8 ]
  • [ 1373316-48-3 ]
YieldReaction ConditionsOperation in experiment
34% With caesium carbonate;copper(I) oxide; In N,N-dimethyl-formamide; at 140℃; for 72h;Inert atmosphere; Synthetic example 6:1 , 1 ,-bis(4-(pyridin-3-yl)phenyl)-1 H,1 'H-2,2'-biimidazole6A mixture of 1H,1'H-2,2'-biimidazole (950 mg, 7.1 mmol), <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> (4.95 g, 21.3 mmol) and Cs2C03 (9.24 g, 28.4 mmol) in DMF (80 mL) was degassed ( 2 bubbling, 15 min). Cu20 (410 mg, 2.9 mmol) was added and the mixture was heated (140 "C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 40:60:3 then 35:60:5 then 30:60:10) to give 1 ,1,-bis(4-(pyridin-3-yl)phenyl)-1 H,1'H-2,2'-biimidazole (1.05 g, 34%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/toluene/petrol) and then by distillation (sublimation apparatus 260 DC, 10"6 mBar): m.p. 218 - 223 C (DSC); 1H NMR (CDCI3, 400 MHz) delta 6.95 - 7.00 (m, 4H), 7.15 (d, J 1.2 Hz, 2H), 7.29 (d, J 1.2 Hz, 2H), 7.38 (ddd, J 0.6, 4.8, 7.9 Hz, 2H), 7.40 - 7.45 (m, 4H), 7.82 (ddd, J 0.6, 1.7, 7.9 Hz, 2H), 8.62 (dd, J 1.4, 4.8 Hz, 2H), 8.79 (d. J 1.9 Hz, 2H); 13C NMR (CDCI3, 100 MHz) delta 121.4, 123.7, 124.8, 127.7, 130.2, 134.1 , 135.2, 137.0, 137.2, 137.3, 148.1 , 149.0; HRMS (El) m/z 439.1665 CzeHig e [M - H]+' requires 439.1666.
 

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