Structure of 118129-60-5
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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. : | 118129-60-5 |
Formula : | C24H6Br2O6 |
M.W : | 550.11 |
SMILES Code : | O=C(C1=CC=C(C2=C(Br)C=C3C4=C2C5=CC=C4C(OC3=O)=O)C6=C5C(Br)=CC7=C16)OC7=O |
MDL No. : | MFCD11870875 |
InChI Key : | WPBVUAVIGWNDGT-UHFFFAOYSA-N |
Pubchem ID : | 11103604 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 32 |
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 | 122.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
86.74 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
6.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
5.16 |
Log S (ESOL):? ESOL: Topological method implemented from |
-7.42 |
Solubility | 0.000021 mg/ml ; 0.0000000382 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-7.47 |
Solubility | 0.0000185 mg/ml ; 0.0000000335 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-9.86 |
Solubility | 0.0000000754 mg/ml ; 0.0000000001 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 |
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 |
-5.48 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) |
2.75 |
* 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 |
---|---|---|
65.2% | With propionic acid; for 16h;Heating / reflux; | Part A: Preparation of N.N'-bis(2-ethylhexylVl,7-dibromoperylene-3,4:9.10- bis(dicarboxiamide) (PDI2EH-Brz)[0199] l,7-Dibromoperylene-3,4:9,10-dianhydride (PDABr2) (5.10 g, 9.35 mmol) was mixed with 2-ethylhexylamine (5.60 mL, 34.2 mmol) in propionic acid (80 mL). The reaction mixture was heated under reflux for 16 hours. After cooling to room temperature, the resulting solid was collected by filtration, washed with propionic acid and several times with MeOH, and dried overnight. Filtration afforded 7.57 g of crude product, which was purified by column chromatography (CHCl3) to give PDI2EH-Br2 as a red solid (5.12 g, 6.63 mmol, yield 65.2 % ). <n="65"/>[0200] M.p. > 200 C; 1H NMR (CDCl3, 500 MHz): delta 9.48 (d, 2H, J = 8.0 Hz), 8.92 (s, 2H), 8.69 (d, 2H, J = 8.0 Hz), 4.20-4.11 (m, 4H), 2.00-1.92 (m, 2H), 1.50- 1.35 (m, 8H), 1.35-1.24 (m, 8H), 0.96 (d, 6H, J = 7.5 Hz), 0.91 (t, 6H, J = 7.0 Hz); Elemental Analysis (calculated: C, 62.19; H, 5.22; N, 3.63): C, 62.20; H, 5.43; N, 3.33. |
50% | With propionic acid; In water; at 142℃; for 3.5h; | 13.1 N,N'-Bis(2-ethylhexyl)-1,7-dibromo-3,4:9,10-tetracarboximide 2.00 g (3.63 mmol) of 1,7-dibromo-3,4:9,10-tetracarboxylic bisanhydride, 4 ml of 2-ethylhexylamine and 25 ml of propionic acid are heated to 142 C. for 3.5 h and then added to 150 ml of water. The solid which precipitates out is filtered off, dried and purified by column chromatography (dichloromethane) to obtain 1.38 g (50%) of the title compound. 1H NMR (400 MHz, CDCl3, TMS): delta=0.88-1.00 (m, 12H), 1.25-1.43 (m, 16H), 1.95 (m, 2H), 4.16 (m, 4H), 8.70 (d, 2H, 3J=8.2 Hz), 8.94 (s, 2H), 9.50 (d, 2H, 3J=8.1 Hz). |
With acetic acid; In 1-methyl-pyrrolidin-2-one; at 80℃; for 6h;Inert atmosphere; | In three 100ml reaction flask were added 0.89g obtained by the above step brominated perylene tetracarboxylic acid anhydride (M = 550), 0.42mL17.5mol / L of glacial acetic acid (M = 60) and 0.63g isooctyl amine (M = 129) was added to the containing 13mLN- methylpyrrolidone (M = 99,1.028g / mL) three-necked reaction flask under argon, the reaction at 80 for about 6 hours.And reaction with CH2C12Gussets observe the extent of reaction.After completion of the reaction, placed to room temperature, and then the product was poured into a beaker containing 200mL deionized water, the precipitated floc dark red, then suction filtered, washed with methanol, and the obtained cake was dried in vacuo at 80 give a dark red solid, and finally with dichloromethane: petroleum ether (v: v) = 5: 1 as eluent was purified by silica gel column chromatography to obtain red powder M2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-methyl-pyrrolidin-2-one; In propionic acid; at 85℃; for 4h;Sonication; | (2) Synthesis of Compound 2: Compound 1 (10 g, 18.18 mmol) was weighed into a 500 ml three-necked flask.Add N-methylpyrrolidone (300 mL) and dissolve by sonication.Add 1-amino-undecanoic acid (8.30 g, 41.23 mmol) and propionic acid (45 ml), and react at 85 ° C for 4 h.The organic solvent was evaporated to dryness under reduced pressure to give compound 2 as a red solid.Without further purification, proceed directly to the next step. |
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