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Chemical Structure| 2217-40-5 Chemical Structure| 2217-40-5

Structure of 2217-40-5

Chemical Structure| 2217-40-5

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Product Details of [ 2217-40-5 ]

CAS No. :2217-40-5
Formula : C10H13N
M.W : 147.22
SMILES Code : NC1CCCC2=C1C=CC=C2
MDL No. :MFCD00001740
InChI Key :JRZGPXSSNPTNMA-UHFFFAOYSA-N
Pubchem ID :18066

Safety of [ 2217-40-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:2735
Packing Group:

Computational Chemistry of [ 2217-40-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 46.58
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.85
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

1.72
Log Po/w (WLOGP)?

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

1.7
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.

2.1
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

2.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.92

Water Solubility

Log S (ESOL):?

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

-2.24
Solubility 0.847 mg/ml ; 0.00575 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.

-1.88
Solubility 1.93 mg/ml ; 0.0131 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

-2.9
Solubility 0.187 mg/ml ; 0.00127 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.

-5.98 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

2.0
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)

1.84

Application In Synthesis of [ 2217-40-5 ]

* 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 [ 2217-40-5 ]

[ 2217-40-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 126-83-0 ]
  • [ 2217-40-5 ]
  • 2-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-ylamino)propane-1-sulfonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Preparation of 2-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-ylamino)propane-1-sulfonic acid (Compound JZ); A solution of 3-chloro-2-hydroxy-1-propanesulfonic acid, sodium salt (2 g, 10 mmol) in water (9.75 mL total volume) was added over 8 hours to a mixture of 1,2,3,4-tetrahydro-1-nahtylamine (2 g, 13.6 mmol), water (10 mL) and 1,4-dioxane (4 mL) at 40 C. The mixture was stirred at this temperature for another 18 hours after the end of the addition. The reaction was not completed. The mixture was heated for 2 hours at reflux. The mixture was diluted with water (10 mL) and 50% w/w NaOH (0.25 mL) was added. The reaction mixture was extracted with chloroform (2×25 mL). It was then concentrated to a thick oil. The solution was applied on a Dowex 50 W 8 column (100 g). The fractions containing the product were concentrated, treated with activated charcoal (no effect) and freeze-dried. The desired material was obtained as a glassy solid (0.85 g, 3 mmol, 30%). The 1H and 13C NMR and MS were consistent with the structure.
  • 2
  • [ 2217-40-5 ]
  • [ 298-12-4 ]
  • [ 23357-46-2 ]
  • [ 529-34-0 ]
YieldReaction ConditionsOperation in experiment
With pyridoxal 5'-phosphate; recombinant ω-transaminase from Burkholderia vietnamiensis G4; In aq. buffer; at 37℃; for 12h;pH 7.4;Resolution of racemate; Enzymatic reaction; General procedure: Racemic amine (10 mM, Table 4) was mixed with glyoxylate (10 mM) in 1 ml of phosphate buffer (100 mM, pH 7.4) containing PLP (20 μM). The reaction was started by adding 0.8 mg/ml of HBV-ω-TA, and the mixture was incubated at 37 C for 12 h. The amount and ee value of the residual amino donor were determined according to Section 2.10.
  • 3
  • [ 2217-40-5 ]
  • [ 98556-31-1 ]
  • C18H16IN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine; In isopropyl alcohol; at 60℃; for 20h;Inert atmosphere; To a solution of <strong>[98556-31-1]4-chloro-6-iodoquinazoline</strong> (500 mg, 1.7 mmol) and 1,2,3,4- tetrahydronaphthalen-1-amine (252 mg, 1.7 mmol) in isopropyl alcohol (30 mL) was added triethylamine (0.7 mL, 5.0 mmol). The resulting solution was heated to 60 C under nitrogen for 20 h. LC-MS analysis showed completed consumption of starting material. The mixture was cooled down and excess isopropyl alcohol was removed by rotary evaporation. The residue was purified by Prep-HPLC to give A28-001 as a yellow solid (400 mg, yield:60%). LC-MS 402 (M+H), purity 100% (UV 214 nm); ‘H NMR (400 MHz, DMSO-d6) ö8.82 (d, J = 2.0 Hz, 1H), 8.62 (d, J = 8.0 Hz, 1 H), 8.53 (s, 1 H), 8.02 (d, J = 8.8 Hz, 1 H),7.48 (d, J = 8.8 Hz, 1 H), 5.73-5.70 (m, 1 H), 2.84-2.8 1 (m, 2 H), 2.03-1.90 (m, 4 H).
  • 4
  • [ 2217-40-5 ]
  • [ 30982-08-2 ]
  • C20H23NO4 [ No CAS ]
  • 5
  • [ 53137-27-2 ]
  • [ 2217-40-5 ]
  • 2,4-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.4% General procedure: To a magnetically stirred suspension of the carboxylic acid derivative1d or 3d (1.6 mmol) in anhydrous DMF were successivelyadded tributylamine (Hunig's base) (6 equiv.) and N,N,N0,N'-Tetramethyl-O-(1H-benzotriazol-1-yl) uronium hexafluorophosphate(HBTU) (1.2 equiv.). The mixture was allowed to stir at room temperaturefor 30 min. The appropriate amine (1.2 equiv.) was thenadded, and the solutionwas stirred at room temperature for 4e5 h.The mixture was diluted with EtOAc, washed with aqueousNaHCO3 solution, 1 N HCl and brine, dried over anhydrous MgSO4and concentrated to give a crude resin. The crude product wasfurther purified using column chromatography.
 

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