Home Cart Sign in  
Chemical Structure| 269410-24-4 Chemical Structure| 269410-24-4

Structure of 269410-24-4

Chemical Structure| 269410-24-4

*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 [ 269410-24-4 ]

CAS No. :269410-24-4
Formula : C14H18BNO2
M.W : 243.11
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC2=C(NC=C2)C=C1
MDL No. :MFCD03789263
InChI Key :FATPQDPUKVVCLT-UHFFFAOYSA-N
Pubchem ID :2734772

Safety of [ 269410-24-4 ]

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

Computational Chemistry of [ 269410-24-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 9
Fraction Csp3 0.43
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 74.77
TPSA ?

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

34.25 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

3.04
Log Po/w (WLOGP)?

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

2.47
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

2.42
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.88

Water Solubility

Log S (ESOL):?

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

-3.57
Solubility 0.066 mg/ml ; 0.000271 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.

-3.43
Solubility 0.0914 mg/ml ; 0.000376 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

-4.89
Solubility 0.00314 mg/ml ; 0.0000129 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

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

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

Yes
Log Kp (skin permeation)?

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

-5.62 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)

2.79

Application In Synthesis of [ 269410-24-4 ]

* 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 [ 269410-24-4 ]

[ 269410-24-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1112982-76-9 ]
  • [ 269410-24-4 ]
  • [ 1204741-84-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 130℃; for 0.5h;Microwave irradiation; Example 2; Preparation of iV-(5-(lH-Indol-5-yl)thiazolo [5,4-6] pyridin-2- yl)acetamide (2); PddppfCI2-CEta2CI2 NaHCO3 (sat ), 1 ,4-diotaoxane, microwave, 110-130 0CExample 1 [0377] A mixture of Example 1 (64 mg, 0.23 mmol), 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-indole (85 mg, 0.35 mmol), PddppfCl2-DCM (cat.), Sat. NaHCO3 (1 mL) and 1,4-dioxane (2 mL) was heated in a microwave at 130 0C for 30 min. The reaction mixture was purified by HPLC to give the titled compound N-(5-(lH-indol-5- yl)thiazolo[5,4-b]pyridin-2-yl)acetamide as a white solid (3.8 mg). 1H NMR (400 MHz, MeOD) delta ppm 8.13 (s, IH), 7.98 (d, J=6 Hz, IH), 7.85 (d, J=6 Hz, IH), 7.72 (d, J=6 Hz, IH), 7.39 (d, J=6 Hz, IH), 7.19 (d, J=4 Hz, IH), 6.46 (d, J=4 Hz, IH), 2.18 (s, 3H); [M+H] calc'd for Ci6H12N4OS, 309; found, 309.
  • 2
  • [ 29840-73-1 ]
  • [ 269410-24-4 ]
  • 2-(1H-indol-5-yl)isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With potassium acetate; In 1,4-dioxane; at 70℃;Inert atmosphere; Sealed tube; General procedure: A mixture of a (243 mg, 1 mmol), 3-Amino-2-bromopyridine (187, 1.1 mmol), PdCl2(dppf) (51 mg, 0.07 mmol) and KOAc (300 g, 3 mmol) were added in 1,4-dioxane (4 ml). The suspension was bubbled with nitrogen for 20 min, and heated in a sealed tube at 60C for 6 h. The reaction process was similar as Zif-1.
  • 3
  • [ 1480-65-5 ]
  • [ 269410-24-4 ]
  • [ 1450994-16-7 ]
  • 4
  • [ 52414-98-9 ]
  • [ 269410-24-4 ]
  • 5-(3-methyl-4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-indole [ No CAS ]
  • 5
  • [ 52414-98-9 ]
  • [ 269410-24-4 ]
  • 5-(3-methyl-4-nitrophenyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 80℃; for 2h; A mixture of 5-(tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole (1000 mg, 4.11 mmol, 1 equiv), 4-bromo-2-methyl-l -nitrobenzene (888.6 mg, 4.11 mmol, 1.000 equiv), K2CO3 (1137.0 mg, 8.23 mmol, 2 equiv) and Pd(dppf)Cl2 (301.0 mg, 0.41 mmol, 0.1 equiv) in dioxane (10.0 mL) was stirred at 80 C for 2 hours. The reaction was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 : 10) as eluent to afford the desired product as a yellow solid in 48% yield.
48% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 80℃; for 2h; A mixture of 5-(tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole (1000 mg, 4.11 mmol, (1366) 1 equiv), 4-bromo-2-methyl-l-nitrobenzene (888.6 mg, 4.11 mmol, 1.000 equiv), K2CO3 (1137.0 mg, 8.23 mmol, 2 equiv) and Pd(dppf)Cl2 (301.0 mg, 0.41 mmol, 0.1 equiv) in dioxane (10.0 mL) was stirred at 80 C for 2 hours. The reaction was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 : 10) as eluent to afford the desired product as a yellow solid in 48% yield.
 

Historical Records

Categories

Related Functional Groups of
[ 269410-24-4 ]

Organoborons

Chemical Structure| 642494-36-8

A172947 [642494-36-8]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.97

Chemical Structure| 1219741-53-3

A126520 [1219741-53-3]

1-Ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.96

Chemical Structure| 642494-37-9

A217937 [642494-37-9]

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.93

Chemical Structure| 388116-27-6

A194704 [388116-27-6]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.91

Chemical Structure| 448955-87-1

A128096 [448955-87-1]

9-(2-Ethylhexyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Similarity: 0.88

Related Parent Nucleus of
[ 269410-24-4 ]

Indoles

Chemical Structure| 642494-36-8

A172947 [642494-36-8]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.97

Chemical Structure| 1219741-53-3

A126520 [1219741-53-3]

1-Ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.96

Chemical Structure| 642494-37-9

A217937 [642494-37-9]

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.93

Chemical Structure| 388116-27-6

A194704 [388116-27-6]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Similarity: 0.91

Chemical Structure| 736990-02-6

A297577 [736990-02-6]

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

Similarity: 0.78