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Structure of N12N
CAS No.: 2783-17-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 2783-17-7 |
Formula : | C12H28N2 |
M.W : | 200.36 |
SMILES Code : | NCCCCCCCCCCCCN |
MDL No. : | MFCD00008155 |
InChI Key : | QFTYSVGGYOXFRQ-UHFFFAOYSA-N |
Pubchem ID : | 17727 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H314-H317 |
Precautionary Statements: | P264-P270-P271-P272-P280-P303+P361+P353-P304+P340-P330-P305+P351+P338-P310-P331-P363-P403+P233-P501 |
Class: | 8 |
UN#: | 3259 |
Packing Group: | Ⅲ |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 11 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 65.21 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.04 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.8 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.8 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.49 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.15 |
Solubility | 282.0 mg/ml ; 1.41 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.19 |
Solubility | 308.0 mg/ml ; 1.54 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.02 |
Solubility | 0.019 mg/ml ; 0.0000946 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-8.09 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
1.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.71 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.3% | In chloroform; for 24h;Reflux; | General procedure: N-(2-Hydroxyethyl)maleimide (1) and the diamine (2a-d) were dissolved in 50 mL of chloroform and refluxed for 24 h. The solvent was removed in vacuo. The residue was chromatographed on a silica gel column to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In ethanol; at 65℃; | Benzyl carbonate (5 g, 21.9 mmol) was dissolved in 10 ml ethanol and was added dropwise to a solution of 1,12-diaminododecane 48 (4.83 g, 24.1 mmol) in 25 ml ethanol. The resulting mixture was stirred overnight at reflux.After cooling to room temperature, 50 ml of ethanol was added, resulting in a precipitate that was removed byfiltration and washed with 100 ml of ethanol. The ethanol was subsequently concentrated to approximately 10 mland stirred with aqueous HCl (450 ml, 1M) for 30 minutes. The resulting salt was collected by filtration, washedwith 1 M HCl, and stirred for 16 hours in aqueous HCl (250 ml, 1M). The solid was collected by filtration andwashed with diethyl ether (2x 100 ml) and dichloromethane (3x 100 ml). The resulting residue was dissolved in200 ml of dichloromethane and 50 ml of ethanol. This solution was washed twice with 50 ml of a 1 M solutionof sodium hydroxide. The aqueous phase was extracted twice with 50 ml dichloromethane and once with 50 mlof chloroform containing 10 % methanol. The combined organic layers were dried over Na2SO4 en concentratedin vacuo to afford the crude product, which was purified by column chromatography using silica, eluting withdichloromethane containing 10-15% methanol and 1-2% triethylamine yielding the pure product (3.33 g, 45 %).1H NMR (400 MHz, CDCl3): delta 1.15 (s, 2H), 1.26 (m, 16H), 1.45 (m, 4H), 2.65 (t, 2H), 3.18 (q, 2H), 5.08 (s,2H), 7.37 (m, 5H) ppm. 13C NMR (400 MHz, CDCl3): delta 26.58, 26.68, 29.11, 29.64, 29.37, 29.40, 29.68, 32.95,40.80, 41.84, 66.38, 75.60, 75.62, 127.79, 127.88, 128.32, 136.50, 156.77 ppm. RP-LCMS: calc. Mw = 334.3g/mol, found m/z: 335.4 [M+H]+. |