Structure of 90-93-7
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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. : | 90-93-7 |
Formula : | C21H28N2O |
M.W : | 324.46 |
SMILES Code : | O=C(C1=CC=C(N(CC)CC)C=C1)C2=CC=C(N(CC)CC)C=C2 |
MDL No. : | MFCD00009044 |
InChI Key : | VYHBFRJRBHMIQZ-UHFFFAOYSA-N |
Pubchem ID : | 66663 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 24 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 103.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.66 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.32 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.06 |
Solubility | 0.00284 mg/ml ; 0.00000875 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.59 |
Solubility | 0.00084 mg/ml ; 0.00000259 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.68 |
Solubility | 0.0000678 mg/ml ; 0.000000209 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.49 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
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) |
2.14 |
* 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 |
---|---|---|
General procedure: Preparation methods of 3,3-diaryl-3H-naphtho[2,1-b]pyrans were generally based on condensation reactions taking place in the apolar solvent as toluene under acid catalysis, which starting from suitable naphthols and propargyl alcohols.[26], [27] and [28]The propargyl alcohol (2) was prepared from the diaryl ketone (1) as outlined in Scheme 1. 10 mmol diaryl ketone (1) was dissolved in 50 mL dry THF and was added dropwise to a solution of 50 mmol sodium acetylide in THF below 0 C. The mixture was then allowed to stir at room temperature for about 3 h until none of the diaryl ketone (1) remained by TLC examination of the reaction mixture. The reaction mixture was poured into iced water for separation. The organic phase was collected and followed by washing with water (3×50 mL) and then dried (anhyd Na2SO4). The propargyl alcohol was then obtained in the yield of about 80% after the short flash chromatography and was used for subsequent procedure directly.273 mmol propargyl alcohol (2), 3 mmol 2-naphthol derivative (3), and 1.0 g p-toluenesulfonic acid (TsOH) were dissolved in 50 mL toluene. The reaction mixture was refluxed for about 2 h until TLC examination indicated that none of the propargyl alcohol remained. The mixture was cooled to room temperature and washed with 1 mol L-1 NaOH solution (2×50 mL) and water. After drying with anhyd Na2SO4, removal of the toluene by vacuum evaporation gave a dark gum. The pure naphthopyran product was obtained by elution from silica using 10% ethyl acetate/hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.3 g | With dihydrogen peroxide; chloranil; Aliquat 336; In chlorobenzene; at 20 - 25℃; | 4,4'-bis(dialkylamino)diphenylmethane (30 g), cobalt complex (3) (0.9 g), tetrachlorophenylhydrazine (0.9 g),Trioctylmethylammonium chloride (1g) and chlorobenzene (100ml) were added to a 250ml four-neck bottle.Add 30% hydrogen peroxide (13.2g) dropwise, add at room temperature, control the temperature 20~25 C, drop,The spot plate is monitored until there is no remaining reaction material.After the end of the reaction, the temperature was lowered, and the temperature was lowered to 5 C, and 30 ml of a 20% sodium hydrogen sulfite solution was added to wash, and the mixture was allowed to stand for liquid separation.The organic phase is distilled off under reduced pressure.The crude tetraethylmethanolone was obtained in an amount of 29 g.The crude product was recrystallized from 29 g of n-heptane.Obtained a pale yellow tetraethylmethanol ketone solid (25.3 g),The content is 99.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.2% | A mixture of 4,4′-bis(diethylamino)-benzophenone (3.0g, 9.3mmol), toluene (30mL), and phosphorus (V) oxychloride (4.2mL, 15.2mmol) was vigorously stirred at 25C for 1h. Subsequently, n-phenyl-9-anthramine (1.0g, 3.7mmol) was added to the mixture. The resulting solution was stirred for 24h at 105C and then cooled to room temperature. The settled mixture was extracted using CH2Cl2 and NaCl brine. The collected organic layers were dried over anhydrous MgSO4 and evaporated. The crude dye mixture was refluxed in an acetone/ethyl acetate (1:3, v/v) binary solvent at 80C for 3h. The final solid product was filtered out and dried at 80C under vacuum for 1 day. Yield: 2.73g, 77.2%; 1H NMR (DMSO-d6, ppm): δ=10.1 (1H, s), 8.22 (2H, d), 7.31 (26H, m), 3.60 (16H, d), 1.20 (24H, t); 13C NMR (DMSO-d6, ppm): δ=12.70, 44.81, 45.46, 112.65, 113.94, 114.54, 114.63, 124.83, 125.58, 126.08, 126.33, 126.77, 127.50, 127.75, 129.55, 130.21, 130.46, 130.96, 131.19, 131.84, 132.71, 133.57, 137.00, 138.97, 139.94, 146.9, 153.82, 154.77, 155.33, 168.85, 169.83, 175.85; MALDI-TOF: m/z 882.57 (100%, [M + H]+); Elemental analysis: Calcd. for C62H69N5Cl2: C,77.96; H, 7.28; N, 7.33%. Found: C, 77.77; H, 7.42; N, 7.52. |