Structure of 156028-26-1
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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. : | 156028-26-1 |
Formula : | C24H4Cl4O6 |
M.W : | 530.10 |
SMILES Code : | O=C(C1=CC(Cl)=C(C2=C(Cl)C=C3C4=C2C5=C(Cl)C=C4C(OC3=O)=O)C6=C5C(Cl)=CC7=C16)OC7=O |
MDL No. : | MFCD08056065 |
InChI Key : | YGRXZLAMYLGXMF-UHFFFAOYSA-N |
Pubchem ID : | 12138167 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 34 |
Num. arom. heavy atoms | 20 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 127.18 |
TPSA ? Topological Polar Surface Area: Calculated from |
86.74 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
7.0 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.97 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.5 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
7.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
5.94 |
Log S (ESOL):? ESOL: Topological method implemented from |
-7.97 |
Solubility | 0.00000566 mg/ml ; 0.0000000107 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-8.64 |
Solubility | 0.00000122 mg/ml ; 0.0000000023 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-10.65 |
Solubility | 0.0000000119 mg/ml ; 0.0 mol/l |
Class? Solubility class: Log S scale |
Insoluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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) |
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 |
-4.56 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
2.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.17 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
4.0 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) |
2.72 |
* 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 |
---|---|---|
80.53% | With propionic acid; for 17h;Heating / reflux; | 5. N,N'-Bis(4-bromo-2,6-diisopropylphenyl)-1,6,7,12-tetrachloro-3,4,9,10-tetracarboxylic acid diimide 10 g (0.019 mol) of 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic dianhydride, 24.16 g (0.094 mol) of <strong>[80058-84-0]4-bromo-2,6-diisopropylaniline</strong> and 250 ml of propionic acid are refluxed for 17 hours under argon in a 500 ml one-necked flask and cooled to room temperature, and the solid formed is subsequently filtered off via a D3 glass frit. The residue is washed in portions with 1 1 of water/methanol (1:3) and dried overnight at 75° C. in a vacuum drying oven. Yield: 15.4 g (80.53percent) of orange-red solid Melting point: >300° C. 1H-NMR spectrum (250 MHz, C2D2Cl4, 25° C.): delta (ppm)=8.68 (s, 4H, H-1), 7.28 (s, 4H, H-2), 2.61 (h, 3J=6.4 Hz, 4H, H-3), 1.18 (d, 3J=4.6 Hz, 24 H, H-4) 13C-NMR spectrum (spin echo experiment, 62.5 MHz, THF-d8, 25° C.): delta (ppm)=162.89 (C=O), 149.59 (arom. q), 136.17 (arom q), 133.80 (arom. CH), 132.72 (arom. q), 130.80 (arom. q), 129.60 (arom. q), 128.27 (arom. CH), 125.34 (arom. q), 124.63 (arom. q), 110.21 (arom. q), 30.09 (CHisopropyl) 24.03 (CH3 isopropyl) FD mass spectrum: m/e (u e0-1)=1001.4 (100percent, M+) (calc.: 1001.98) UV spectrum (CHCl3): lambdamax (epsilon)=427 (11078), 488 (33922), 522 nm (49517 1 mol-1 cm-1) IR spectrum: nu=1704 (nuC=O), 1663 (nuC=O), 1585, 1401, 1356, 1301, 1201, 852 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; at 100℃; for 12h; | To a 100 mL flask 1,6,7,12-tetrachloroperylene tetracarboxylic acid dianhydride 530.1 (5.0 g), <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (3.6 g) and imidazole (20 g) were stirred at 100 C for 12 hours. Thereafter, methanol (200 g) was added thereto, and the formed solid was filtered to obtain a compound represented by the following formula (A-4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; at 100℃; for 12h; | To a 100 mL flask 1,6,7,12-tetrachloroperylene tetracarboxylic acid dianhydride (5.0 g), <strong>[6299-67-8]2,3-dimethoxyaniline</strong> (3.6 g) and imidazole (20 g) were stirred at 100 C for 12 hours. Thereafter, methanol (200 g) was added thereto, and the formed solid was filtered to obtain a compound represented by the following formula (A-7). |
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