Home Cart Sign in  
Chemical Structure| 15463-09-9 Chemical Structure| 15463-09-9

Structure of 15463-09-9

Chemical Structure| 15463-09-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 15463-09-9 ]

CAS No. :15463-09-9
Formula : C10H9NO
M.W : 159.19
SMILES Code : OC1=CC=C2C(C)=CC=NC2=C1
MDL No. :MFCD06245596
InChI Key :GXFFWHIKMRPHIV-UHFFFAOYSA-N
Pubchem ID :135491854

Safety of [ 15463-09-9 ]

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

Computational Chemistry of [ 15463-09-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 10
Fraction Csp3 0.1
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 48.73
TPSA ?

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

33.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.65
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

2.25
Log Po/w (WLOGP)?

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

2.25
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.

1.49
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

2.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.02

Water Solubility

Log S (ESOL):?

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

-2.86
Solubility 0.219 mg/ml ; 0.00138 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.

-2.58
Solubility 0.417 mg/ml ; 0.00262 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

-3.5
Solubility 0.0503 mg/ml ; 0.000316 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

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

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.

-5.67 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)

1.09

Application In Synthesis of [ 15463-09-9 ]

* 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 [ 15463-09-9 ]

[ 15463-09-9 ] Synthesis Path-Downstream   1~8

  • 4
  • [ 15463-09-9 ]
  • [ 196195-13-8 ]
  • 6-methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-morpholinopropoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h; Example 4 A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225mg, 0.67mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106mg, 0.77mmol) and <strong>[15463-09-9]7-hydroxy-4-methylquinoline</strong> (122mg, 0.77mmol), (Chem. Berich. 1967, 100, 2077), in DMF (7.5ml) was stirred at 100C for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40ml) and stirred at ambient temperature for a few minutes. The crude solid was collected by filtration washing with water. The resultant solid was dissolved in dichloromethane (2ml) and was filtered through phase separating paper. The filtrate was evaporated under vacuum to give a solid residue which was triturated with ether, filtered and dried to give 6-methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-morpholinopropoxy)quinazoline (175mg, 57%). 1H NMR Spectrum: (DMSOd6) 1.98(m, 2H); 2.39(m, 4H); 2.48(t, 2H); 2.71 (s, 3H); 3.59(m, 4H); 4.00(s, 3H); 4.26(t, 2H); 7.40(s, 1H); 7.41(m, 1H); 7.61(dd, 1H); 7.62(s, 1H); 7.90(d, 1H); 8.20(d, 1H); 8.52(s, 1H); 8.78(d, 1H) MS (ESI): 461 (MH)+
  • 5
  • [ 199327-69-0 ]
  • [ 15463-09-9 ]
  • 6-methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 15 Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13g, 0.4mmol), (prepared as described for the starting material in Example 9), was reacted with <strong>[15463-09-9]7-hydroxy-4-methylquinoline</strong> (80mg, 0.5mol), (Chem. Berich. 1967, 100, 2077), to give 6-methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (155mg, 87%). 1H NMR Spectrum: (DMSOd6) 1.7(br s, 4H); 2.05(m, 2H); 2.5(br s, 4H); 2.6(t, 2H); 2.75(s, 3H); 4.02(s, 3H); 4.3(t, 2H); 7.41(s, 1H); 7.45(d, 1H); 7.65(s, 1H); 7.65(d, 1H); 7.95(s, 1H); 8.25(d, 1H); 8.55(s, 1H); 8.8(d, 1H) MS (ESI): 445 [MH]+
  • 6
  • [ 15463-09-9 ]
  • [ 264208-72-2 ]
  • 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(4-methylquinolin-7-yloxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 13 Using a procedure analogous to that described for Example 10, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (130mg, 0.4mmol), (prepared as described for the starting material in Example 10), was reacted with 4-methyl-7-hydroxyquinoline (80mg, 0.5mol), (Chem. Ber. 1967, 100, 2077), to give 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(4-methylquinolin-7-yloxy)quinazoline (160mg, 90%). 1H NMR Spectrum: (DMSOd6) 1.3-1.5(m, 2H); 1.7-1.95(m, 3H); 1.9(t, 2H); 2.17(s, 3H); 2.74(s, 3H); 2.8(d, 2H); 4.07(s, 3H); 4.1(d, 2H); 7.4(m, 2H); 7.65(dd, 1H); 7.65(s, 1H); 7.9(s, 1H); 8.21(d, 1H); 8.54(s, 1H); 8.78(d, 1H) MS (ESI): 445 [MH]+
  • 7
  • [ 288384-41-8 ]
  • [ 15463-09-9 ]
  • 6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)-4-(4-methylquinolin-7-yloxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 2.0h; Example 155 A mixture of 4-chloro-6-methoxy-7-(3-(N -methyl-N -methylsulphonylamino)propoxy)quinazoline (150 mg, 0.42 mmol), (prepared as described for the starting material in Example 152), potassium carbonate (90 mg, 0.63 mmol) and <strong>[15463-09-9]7-hydroxy-4-methylquinoline</strong> (71 mg, 0.46 mmol), (Chem. Berich. 1967, 100, 2077), in DMF (5.0 ml) was stirred at 100 C for 2 hours and allowed to cool to ambient temperature. The DMF solvent was removed by evaporation and the residue was taken up in 2N aqueous sodium hydroxide solution. The precipitate was filtered off, dried, taken up in dichloromethane and then filtered through phase separating paper. The solution was then evaporated to dryness. The resulting solid was recrystallized from acetonitrile, filtered and washed with diethyl ether to give 6-methoxy-7-(3-(N -methyl-N -methylsulphonylamino)propoxy)-4-(4-methylquinolin-7-yloxy)quinazoline (84mg, 42%). 1H NMR Spectrum: (DMSOd6) 2.09 (m, 2H), 2.71 (s, 3H), 2.79 (s, 3H), 2.89 (s, 3H), 3.25 (t, 2H), 3.98 (s, 3H), 4.25 (t, 2H), 7.37 (s, 1H), 7.38 (d, 1H), 7.61 (dd, 1H), 7.63 (s, 1H), 7.89 (d, 1H), 8.20 (d, 1H), 8.54 (s, 1H) and 8.76 (d, 1H) MS (ESI): 483 (MH)+
  • 8
  • [ 15463-09-9 ]
  • C17H23N5O4 [ No CAS ]
  • C27H30N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20.0℃; To a solution of intermediate 24 (700 mg, theoretically 1 .94 mmol) and 4- mcthylquinolin-7-ol (370 mg, 2.32 mmol ) in THF (20 mL) were added triphenylphosine (624 mg, 2.71 mmol) and DBAD ( 71 1 mg. 2.71 mmol). The mixture was stirred overnight at room temperature and was then evaporated in vacuo. The crude was purified by preparative LC ( irregular SiOH, 15-40 mupiiota, 50 g, Merck, dry loading (Celite) mobile phase gradient: from Heptane 80%, EtOAc 18%, MeOH 2% to Heptane 10%, EtOAc 81%, MeOH 9%) to give intermediate 73 as an off-white foam (697 mg, 67% yield).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 15463-09-9 ]

Alcohols

Chemical Structure| 580-20-1

A210867 [580-20-1]

Quinolin-7-ol

Similarity: 0.95

Chemical Structure| 578-67-6

A224771 [578-67-6]

5-Hydroxyquinoline

Similarity: 0.90

Chemical Structure| 23432-39-5

A281546 [23432-39-5]

6-Methoxyquinolin-4-ol

Similarity: 0.88

Chemical Structure| 116529-84-1

A197917 [116529-84-1]

6-Methylquinolin-5-ol

Similarity: 0.87

Chemical Structure| N/A

A324377 [N/A]

2,7-Dihydroxyquinoline

Similarity: 0.86

Related Parent Nucleus of
[ 15463-09-9 ]

Quinolines

Chemical Structure| 6238-12-6

A308640 [6238-12-6]

7-Methoxy-4-methylquinoline

Similarity: 0.97

Chemical Structure| 1807542-80-8

A429970 [1807542-80-8]

7-Methoxy-4-methylquinoline hydrochloride

Similarity: 0.95

Chemical Structure| 580-20-1

A210867 [580-20-1]

Quinolin-7-ol

Similarity: 0.95

Chemical Structure| 4964-76-5

A149896 [4964-76-5]

7-Methoxyquinoline

Similarity: 0.93

Chemical Structure| 578-67-6

A224771 [578-67-6]

5-Hydroxyquinoline

Similarity: 0.90