Structure of 1046864-83-8
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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. : | 1046864-83-8 |
Formula : | C24H24N2O6S2 |
M.W : | 500.59 |
SMILES Code : | O=C(N1C(C(C2=C1C3=CC=CS3)=C(C4=CC=CS4)N(C(OC(C)(C)C)=O)C2=O)=O)OC(C)(C)C |
MDL No. : | MFCD28098465 |
InChI Key : | JWVNTGQABFZACQ-UHFFFAOYSA-N |
Pubchem ID : | 59629049 |
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 | 18 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 133.8 |
TPSA ? Topological Polar Surface Area: Calculated from |
153.08 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.91 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.3 |
Solubility | 0.0025 mg/ml ; 0.00000499 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-6.88 |
Solubility | 0.0000667 mg/ml ; 0.000000133 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.84 |
Solubility | 0.000719 mg/ml ; 0.00000144 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
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) |
No |
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) |
No |
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 |
-6.54 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
1.0 |
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 |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
4.2 |
* 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 |
---|---|---|
50% | With N-Bromosuccinimide; at 20.0℃; for 40h;Darkness; | T-Boc TPP (2.36 g, 4.71 mmol) was added to CF in a 2-neck round bottom flask and stirred at room temperature.After light protection using an aluminum foil, NBS (2.09 g, 2.5 eq.) Was added and stirred for 40 hours or more.The reaction was monitored by TLC. When the reaction proceeded, the crude mixture was immediately evaporated and the CF / EtOHTo obtain a dark needle-like compound (Yield: 50%). |
50% | With N-Bromosuccinimide; at 20.0℃;Darkness; | The t-l3oc TPP (2.36 g, 4.71 mmol) was added to CF in a 2-neck round bottom flask, and the mixture was stirred at room temperature. Light protection was performed by using an aluminum foil, and then N135 (2.09 g, 2.5 eq.) was added thereto and the mixture was stirred for 40 hours or more. It was confirmed through TLC whether the reaction proceeded, and if the reaction proceeded, the crude mixture was immediately evaporated and recrystallization was performed by using CF/EtOH, thereby obtaining 1.6 g (yield:50%) of Compound 2 having a dark brown needle shape. The NMR result of Compound 2 is illustrated in the following FIG. 4, and the MS data thereof are illustrated in the following FIG. 5. |
With N-Bromosuccinimide; In chloroform; for 12h;Darkness; | 3.0 g (6.0 mmol) of the compound represented by the chemical formula (1-1), 2.5 g (13.8 mmol) of N-bromosuccinimide and 200 mL of chloroform were placed in a 500 mL eggplant flask and shielded from light C for 12 hours. Next, after distilling off the solvent under reduced pressure, 100 mL of MeOH was added. Further, the precipitate was collected by filtration to obtain 3.1 g (yield: 78.8%) of a compound represented by the chemical formula (1-4) which is a dark green powder. The compound represented by the chemical formula (1-4) had m / z of 658.9, 656.9, and 660.9 ([M+H] +) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | 2 spherical round bottom flaskTPP (4.0 g, 13.3 mmol) was added to a 2-neck round bottom flaskDimethylaminopyridine was added to the catalyst, and the mixture was stirred for about one hour.Then, di- (t-butyl) -dicarbonate (7.26 g, 33.2 mmol) was dissolved in anhydrous THF under nitrogen atmosphere using a syringe and stirred at RT for 12 hours .After the reaction was confirmed by TLC, the THF was reduced in pressure. After silica packing with hexane + Et3N as an eluent and loading the reaction mixture, the impurities were removed by flowing Hx: EA = 4: 1, and chloroform was added thereto. Respectively.After completion of the column, the solvent was removed by decompression, followed by washing with hexane and drying well in a vacuum oven to obtain 4.0 g (yield: 60%) of a dark brown solid compound t-Boc TPP. | |
60% | TPP (4.0 g, 13.3 mmol) was dissolved in an anhydride THF in a 2-neck round bottom flask, and then, dimethylamonopyridine as a catalyst was added thereto, and the resulting mixture was stirred for about 1 hour. And then, di-(t-butyl)-dicarbonate (7.26 g, 33.2 mmol) was dissolved well in the anhydride THF, the solution was added to the flask under a nitrogen condition by using a syringe, and the resulting mixture was stirred at R.T. for 12 hours. The reaction was confirmed by TLC, and after the reaction was terminated, the THF was placed under reduced pressure. Silica packing was achieved by using hexane +Et3N as an eluent, and the reaction mixture was loaded, and then flowed at Hx:EA=4: 1 to remove impurities, and chloroform was flowed. Afier the column chromatography, pressure was reduced to remove the solvent, and the residue was washed with hexane and dried well in a vacuum oven, thereby obtaining 4.0 g of a dark brown solid compound t-Boc TPP (yield: 60%). The NMR result of Compound 1 is illustrated in the following FIG. 2, and the MS data thereof are illustrated in the following FIG. 3. | |
54.1% | With dmap; In tetrahydrofuran; at 20.0℃; for 15h; | 4.0 g (13.3 mmol) of the compound represented by the chemical formula (2-1), 12.0 g (54.9 mmol) of Di-tertbutyl dicarbonate, 200 mL of dry THF and 3.3 g (26.7 mmol) of dimethylaminopyridine (DMAP) , Placed in a 500 mL recovery flask, and then stirred at room temperature for 15 hours. Next, after distilling off the solvent under reduced pressure, 100 mL of MeOH was added. Further, the precipitate was collected by filtration and then purified using silica gel column chromatography (solvent: dichloromethane) to obtain 3.6 g (yield: 54.1) of the compound represented by the chemical formula (1-1) which is a red powder %) Was obtained. The compound represented by the chemical formula (1-1) had m / z of 501.01 ([M + H] +) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 250.0℃;Inert atmosphere; | 50 mg (0.10 mmol) of the compound represented by the chemical formula (1-1) was placed in an Al pan and then heated in a nitrogen atmosphere at 20 C./min using a thermal analyzer EXSTRA 6200 (manufactured by Seiko Instruments Inc.) at 250 C. And the weight change (TG) was measured to obtain 29 mg (yield quant.) Of the compound represented by the chemical formula (2-1) which is a dark purple solid. The compound represented by the chemical formula (2-1) had m / z of 300.1 ([M + H] +) |
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