Structure of 2050-48-8
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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. : | 2050-48-8 |
Formula : | C12H8Br2O2S |
M.W : | 376.06 |
SMILES Code : | O=S(C1=CC=C(Br)C=C1)(C2=CC=C(Br)C=C2)=O |
MDL No. : | MFCD00017836 |
InChI Key : | QBNABJXQGRVIRA-UHFFFAOYSA-N |
Pubchem ID : | 95927 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 73.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.52 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.22 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.13 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.64 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.02 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.22 |
Solubility | 0.00226 mg/ml ; 0.00000602 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.82 |
Solubility | 0.00565 mg/ml ; 0.000015 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.49 |
Solubility | 0.000123 mg/ml ; 0.000000327 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) |
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 |
-5.6 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
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) |
2.12 |
* 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 |
---|---|---|
86% | With oxygen; epi-Cercosporin; In methanol; at 25℃; for 24h;Irradiation; | In a 10 mL reaction tube, cercosporin (0.005 mmol) and 4,4'-dibromophenyl sulfide (0.5 mmol) were sequentially added.2mL of methanol, then oxygen protection, 15W white light irradiation, room temperature 25 C reaction for 24h.Rapid object separated by thin layer silica gel plates 300-500 The reaction solution was evaporated to dryness using a rotary evaporator the solvent used is acetic acid eluent ethyl acetate / petroleum ether (v: v = 1: 5),4,4'-Dibromophenyl sulfone was obtained in a yield of 86%. |
84.66% | With dihydrogen peroxide; acetic acid; for 24h;Reflux; | To a solution of 30mL H2O2 (30%, g/g) and 30mL of HOAc was added 3c (3.44g, 10mmol) in fractions. After heated under reflux for 24h, the resulting mixture was cooled to room temperature and then poured into water. The white precipitate was filtered and dried. The crude product was recrystallized from ethanol to produce 3b as a white solid. Yield: 84.66%. M.p.:173-174C. 1H NMR (300MHz, CDCl3): delta(ppm) 7.80-7.77 (d, J=8.7Hz, 4H), 7.67-7.64 (d, J=8.7Hz, 4H) [36]. |
51% | With dihydrogen peroxide; acetic acid; at 100℃; for 10h; | Well dried 250 mL three-necked round bottom flask charged with bis (4-bromophenyl) sulfane (9 g, 26.2 mmol), 30% hydrogenperoxide 50 mL and acetic acid 100 mL was stirred at 100C for 10 hours. After completion of the reaction, it was extracted three times using methylenechloride (MC). The extracted organic layer was dried to remove water using MgSO4 and the solvent was removed using a rotary evaporator, separated by column chromatography using MC to obtain compound 5 g (yield = 51%). |
With dihydrogen peroxide; acetic acid; for 8h;Inert atmosphere; Reflux; | In N2Gas purification system, and the acetic acid was stirred into compound G.Added in excess 30% hydrogen peroxide.The mixture was refluxed for 8 hours at the temperature 110 reaction was complete.The mixture was cooled to room temperature, water was added and the precipitate.The mixture was stirred for about 30 minutes, the precipitate is filtered off.The resultant was washed with water, to obtain a compound H. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 40℃; for 10h; | In a three-necked flaskDiphenylthiophenol (4g, 0.021mol) was added to it.Connect the three links and add balloons,Br2 (9.95 g, 0.063 mol) was poured in a syringe and stirred at room temperature for 2 h to give a yellow solid.The above yellow solid was dissolved in DCM, and stirred at 2.5 eq.After cooling to room temperature, a white precipitate appeared after stirring with K2CO3.The filtrate was filtered and evaporated to dryness to give a white solid. | |
With dihydrogen peroxide; acetic acid; for 10h; | Diphenylsulfane (4 g, 0.021 mol) and Br2 (9.95 g, 0.063 mol) wereadded into a flask to stir at room temperature for 6h. After that, 300 mLmixed solution of H2O2:CH3COOH 1:1 (v: v) was added to react for 10h, and was further purified by silica gel column chromatography to givewhite solid, with yield of 73%. 1H NMR (400 MHz, Chloroform-d) 7.81-7.76 (m, 4H), 7.68-7.63 (m, 4H). 13C NMR (101 MHz, Chloroformd) 141.63, 133.18, 129.28, 127.66. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With iron(III) chloride; In dichloromethane; at 40℃; for 6h; | 4-Bromobenzenesulfonyl chloride (5.00 g, 19.69 mmol) and bromobenzene (4.61 g, 29.54 mmol) were added to a 250 mL three-necked flask.Dissolve in 40 mL of dichloromethane and add ferric chloride (6.34 g,After 39.39 mmol), the reaction solution was heated to 40 C and stirred for 6 h.The reaction solution was cooled to room temperature, and 30 mL of dichloromethane was slowly added thereto.50 mL of 1 M dilute hydrochloric acid and stirring for 10 min, the mixed solution was poured into a separatory funnel, the organic layer solution was taken, and the aqueous layer was extracted three times with dichloromethane.The organic layers were combined, dried over anhydrous sodium sulfate and filtered.The resulting filtrate was spin-dried using a rotary evaporator.The crude product was purified by silica gel column chromatography using a mixture of n-hexane and dichloromethane in a volume ratio of 4:5. The product was dried in vacuo to give a white powder.6.48 g, yield 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Typical examples of the compound represented by the formula (5) include 4,4'-difluorobenzophenone, ... 4,4'-dichlorodiphenylsulfone, 4,4'-dichloro-3,3'-disulfodiphenylsulfone, dipotassium salt of 4,4'-dichloro-3,3'-disulfodiphenylsulfone, disodium salt of 4,4'-dichloro-3,3'-disulfodiphenylsulfone, 4,4'-dibromodiphenylsulfone, 4,4'-dinitrodiphenylsulfone, 2,6-difluorobenzonitrile, 2,6-dichlorobenzonitrile, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper diacetate; In acetonitrile; at 60℃; for 3h; | General procedure: A mixture of the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.21% | To a solution of 3b (0.376g, 1.0mmol), 18-crown-6 (0.027g, 0.1mmol) and 3,6-di(tert-butyl)carbazole (0.68g, 2.4mmol) in DMPU (5mL) was added K2CO3 (0.55g, 4.0mmol). The reaction mixture was then purged with nitrogen for ten minutes before adding CuI (0.020g, 0.1mmol). The following procedure was similar to that used for 1a. Yield: 58.21%. M.p.:367-370C. 1H NMR (300MHz, CDCl3): delta (ppm) 8.26-8.23 (d, J=8.4Hz, 4H), 8.13 (s, 4H), 7.83-7.80 (d, J=8.4Hz, 2H), 7.50-7.43 (m, 8H), 1.46 (s, 36H). 13C NMR (75MHz, CDCl3): delta (ppm) 143.7, 142.8, 138.4, 137.9, 129.2, 126.2, 123.7, 123.6, 116.1, 108.8, 34.4, 31.6. MS (MALDI-TOF) [m/z]: calcd for C52H56N2O2S, 772.41; found, 772.5745. Anal. Calcd. for C52H56N2O2S (%): C, 80.79; H, 7.30; N 3.62; S, 4.15.found:C, 80.62; H, 7.38; N 3.67; S, 4.17. |
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