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Chemical Structure| 1160790-18-0 Chemical Structure| 1160790-18-0

Structure of 1160790-18-0

Chemical Structure| 1160790-18-0

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Product Details of [ 1160790-18-0 ]

CAS No. :1160790-18-0
Formula : C12H16BN3O2
M.W : 245.09
SMILES Code : CC1(C)C(C)(C)OB(C2=CN3C(C=C2)=NC=N3)O1
MDL No. :MFCD16659797
InChI Key :QXPSJGKDBGYOEX-UHFFFAOYSA-N
Pubchem ID :58446374

Safety of [ 1160790-18-0 ]

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

Computational Chemistry of [ 1160790-18-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 9
Fraction Csp3 0.5
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 69.46
TPSA ?

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

48.65 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

1.73
Log Po/w (WLOGP)?

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

1.03
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.

1.17
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

0.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.84

Water Solubility

Log S (ESOL):?

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

-2.75
Solubility 0.432 mg/ml ; 0.00176 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.

-2.37
Solubility 1.05 mg/ml ; 0.00428 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

-3.32
Solubility 0.118 mg/ml ; 0.000481 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

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

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.

-6.57 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)

2.98

Application In Synthesis of [ 1160790-18-0 ]

* 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 [ 1160790-18-0 ]

[ 1160790-18-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 356560-80-0 ]
  • [ 73183-34-3 ]
  • [ 1160790-18-0 ]
YieldReaction ConditionsOperation in experiment
47% With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); potassium acetate;Inert atmosphere; The A48-1 (180mg, 0.91mmol), bis (pinacolato) borate (348mg, 1.37mmol), 1,1'- bis (diphenylphosphino) ferrocene palladium (II)(37mg, 0.045mmol), potassium acetate (180mg, 1.83mmol) was dissolved in tetrahydrofuran (10mL). Under nitrogen for 8h at 80 , cooled toAt room temperature, filtered through celite, the solvent was evaporated under reduced pressure to give a dark solid (300mg, content: 74%).
A solution of 6-bromo-[1 ,2,4]triazolo[1 ,5-a]pyridine (0.15 g, 0.75 mmol), bispinacolatodiboron (0.29 g, 1.14 mmol) and KOAc (0.11 g, 1.13 mmol) in 1 ,4- dioxane (5.0 ml_) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.025 g, 0.09 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.038 g, 0.037 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 1000C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 246.10 (M+H)+.
With potassium acetate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 80℃;Inert atmosphere; Under an argon atmosphere, 277 mg (0.303 mmol) of tris-(dibenzylidene-acetone)-dipalladium(0) and 224 mg (0.727 mmol) of tricyclohexylphosphine were dissolved in 30 ml dioxane. J410 mg(5.555 mmol) of 4,4,4'4'5,5,5'5'-octamethyl-2,2'-bi-l,3,2-dioxaborolan, 1000 mg (5.050 mmol) of the compound from example 49 A and 743 mg (7.575 mmol) potassium acetate were added and the mixture was stirred overnight at 800C. After cooling, dioxane was added to the reaction mixture and it was filtered on Celite. The filtrate was concentrated in a rotary evaporator at reduced pressure and dried under high vacuum. We obtained 2520 mg of 6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)[l,2,4]triazolo[l,5-a]pyridine as raw product, which was reacted further without further purification.
 

Historical Records

Categories

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[ 1160790-18-0 ]

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