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Structure of 4105-21-9

Chemical Structure| 4105-21-9

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Product Details of [ 4105-21-9 ]

CAS No. :4105-21-9
Formula : C13H10N2
M.W : 194.23
SMILES Code : C12=NC(C3=CC=CC=C3)=CN1C=CC=C2
MDL No. :MFCD00219254
InChI Key :KDHWCFCNNGUJCP-UHFFFAOYSA-N
Pubchem ID :201136

Safety of [ 4105-21-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4105-21-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 15
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 60.63
TPSA ?

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

17.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.4
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

2.9
Log Po/w (WLOGP)?

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

3.0
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.

2.27
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

2.52
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.62

Water Solubility

Log S (ESOL):?

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

-3.55
Solubility 0.0553 mg/ml ; 0.000285 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.

-2.92
Solubility 0.231 mg/ml ; 0.00119 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

-4.61
Solubility 0.00481 mg/ml ; 0.0000248 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

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

Yes
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

Yes
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.

-5.43 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)

2.05

Application In Synthesis of [ 4105-21-9 ]

* 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 [ 4105-21-9 ]

[ 4105-21-9 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 3032-81-3 ]
  • [ 4105-21-9 ]
  • [ 1416319-55-5 ]
YieldReaction ConditionsOperation in experiment
68% With tricyclohexylphosphine tetrafluoroborate; palladium diacetate; potassium carbonate; trimethylpyruvic acid; In N,N-dimethyl acetamide; at 100℃; for 12h;Inert atmosphere; Compound was obtained following the representative procedure, using 2-phenylimidazo[1,2-a]pyridine 2 (300 mg, 1.5 mmol, 1 equiv), <strong>[3032-81-3]1,3-dichloro-5-iodobenzene</strong> (410 mg, 1.5 mmol, 1 equiv) and heating for 12 h. The crude product was purified by silica gel chromatography using dichloromethane as eluent and trituration with methanol afforded 3-(3,5-dichlorophenyl)-2-phenylimidazo[1,2-a]pyridine 19 as a white powder (347 mg, 68percent yield). Rf = 0.60 (petroleum ether/EtOAc: 7/3); Mp = 210-211 °C. 1H NMR (400 MHz, DMSO-d6): delta 8.19 (d, 1H, 3J = 6.8 Hz, H5), 7.84 (t, 1H, 4J = 1.6 Hz, He), 7.73 (d, 1H, 3J = 9.2 Hz, H8), 7.65 (d, 2H, 4J = 1.6 Hz, Hd), 7.61 (d, 2H, 3J = 7.2 Hz, Ha), 7.42-7.32 (m, 4H, H7, Hb and Hc), 6.98 (dd, 1H, 3J = 3J' = 6.8 Hz, H6). 13C NMR (100 MHz, DMSO-d6): delta 144.55 (C), 142.40 (C), 135.27 (2C-Cl), 133.86 (C), 133.16 (C), 129.61 (2Cd), 128.87 (Ce), 128.64 (2Cb), 127.96 (Cc), 127.85 (2Ca), 125.96 (C7), 124.43 (C5), 118.18 (C), 117.05 (C8), 113.16 (C6). IR (KBr) cm-1: 3036 (nuC-Har), 1590, 1560 (nuC=C and nuC=N), 776, 750 (nuC-Cl). MS (ESI) m/z (percent): 339.0 (100) [M + H]+, 341.0 (80) [M + H + 2]+, 343.0 (15) [M + H + 4]+. Anal. Calcd for C19H12Cl2N2: C, 67.27; H, 3.57; N, 8.26. Found: C, 67.50; H, 3.23; N, 7.98.
  • 2
  • [ 399-25-7 ]
  • [ 4105-21-9 ]
  • 3-(1-(2-fluorophenyl)-2-nitroethyl)-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
  • 3
  • [ 54439-75-7 ]
  • [ 4105-21-9 ]
  • C21H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; water; at 150℃; for 24h; In a 10 ml flask,Add the magnet,2-phenylimidazo [1,2-a] pyridine (0.3 mmol) was added,<strong>[54439-75-7]2-<strong>[54439-75-7]chloro-4-methoxybenzaldehyde</strong></strong> (0.9 mmol)Potassium carbonate (0.9 mmol),Tetrabutylammonium bromide (0.9 mmol),Palladium acetate (5 molpercent),4,5-bis (diphenylphosphino) -9,9-dimethylXanthene (10molpercent),N, N-dimethylacetamide (4 mL),Water (0.1 mL).The reaction mixture was reacted at 150 ° C for 24 hours,Cooled to room temperature,An appropriate amount of water was added and extracted three times with ethyl acetate,Combine organic phase,Dried over anhydrous magnesium sulfate,Concentrated by filtration, concentrated column chromatography,Separated product 85mg,Yield 87percent.
  • 4
  • [ 61929-24-6 ]
  • [ 4105-21-9 ]
  • 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)-1,3,4-thiadiazole [ No CAS ]
  • 5
  • [ 4105-21-9 ]
  • [ 802919-90-0 ]
  • 3-(difluoro(phenylsulfonyl)methyl)-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
  • 6
  • [ 1195-33-1 ]
  • [ 4105-21-9 ]
  • [ 1310492-88-6 ]
  • 7
  • [ 2645-22-9 ]
  • [ 4105-21-9 ]
  • 2-phenyl-3-(pyridin-4-ylthio)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With ammonium iodide; water; acetic acid; dimethyl sulfoxide; at 110℃; for 6h;Green chemistry; General procedure: N-heteroarene (0.25 mmol), diorganyl dichalcogenide (0.125 mmol) NH4I (0.025 mmol, 10 molpercent, 3.6 mg), acetic acid (1 eq.) and the mixture of DMSO/H2O (2.5:2.5 eq.) were placed into a round-bottom flask. The reaction was stirred at 110 °C in an oil bath for appropriate time (Tables 3-6). After the completion of the reaction, the mixture was cooled to room temperature, quenched with water and the aqueous layer was extracted with EtOAc. The organic phase was dried over MgSO4, filtered, and the volatiles were completely removed under vacuum to give the crude product. Purification by flash chromatography on silica with a mixture of Hexane/EtOAc as eluent furnished the desired chalcogenated product.
  • 8
  • [ 67-56-1 ]
  • [ 1869-24-5 ]
  • [ 4105-21-9 ]
  • N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium permanganate; di-tert-butyl peroxide; sodium t-butanolate; at 130℃; for 8h; The preparation method comprises the following steps: adding 0.1 mmol of 2-phenylimidazo[1,2-a]pyridine compound to a 35 mL high pressure tube under an air atmosphere.0.2 mmol of <strong>[1869-24-5]2-(trifluoromethyl)benzenesulfonamide</strong>,0.2 mmol of di-tert-butyl peroxide, 0.1 mmolPotassium permanganate, 0.1 mmol of sodium t-butoxide, hexafluoroisopropanol and methanol (volume ratio 1:9) 2 mL, reacted at 130 C for 8 hours;After completion, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to100/0), dried to a yellow solid, yield 84%.
  • 9
  • [ 67-56-1 ]
  • [ 42182-27-4 ]
  • [ 4105-21-9 ]
  • 2-((2-phenylimidazo[1,2-a]pyridin-3-yl)methylamino)isonicotinonitrile [ No CAS ]
 

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