Structure of 90-90-4
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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. : | 90-90-4 |
Formula : | C13H9BrO |
M.W : | 261.11 |
SMILES Code : | O=C(C1=CC=C(Br)C=C1)C2=CC=CC=C2 |
MDL No. : | MFCD00000103 |
InChI Key : | KEOLYBMGRQYQTN-UHFFFAOYSA-N |
Pubchem ID : | 7030 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 64.02 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.52 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.12 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.68 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.66 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.61 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.51 |
Solubility | 0.00799 mg/ml ; 0.0000306 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.18 |
Solubility | 0.0171 mg/ml ; 0.0000653 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.72 |
Solubility | 0.0005 mg/ml ; 0.00000191 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-4.97 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.49 |
* 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 |
---|---|---|
1.0 g of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> as the intermediate of preparation example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to -78 degree C, and 1.613 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 min, and 1.05 g of 4-bromobenzophenone was added. The mixture was stirred at the same temperature for 40 minutes, and then further stirred at room temperature for an additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reaction mixture was extracted with ethyl ether. The organic layer was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was then dispersed in ethanol, stirred for one day, filtered and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 ml of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding 8-(4-bromophenyl)-8-phenyl-8H-indolo-[3,2,1-de]acridine compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With oxygen; copper diacetate; potassium carbonate; aniline; In dimethyl sulfoxide; at 120℃;Schlenk technique; Sealed tube; | General procedure: An oven-dried Schlenk tube was charged with a magnetic stir-bar, 1,2-diarylalkynes 1 (0.5mmol), aniline (0.6mmol), K2CO3 (0.5mmol), Cu(OAc)2 (0.075mmol), DMSO (3mL), The tube was sealed, and oxygen was purged through syringe. Reaction was stirred at 120C for 16-18h. After the reaction was finished, the reaction mixture was diluted in 30mL ethyl acetate, filtered on Celite pad. The organic portion was washed with a saturated solution of brine (8mL), saturated NH4Cl (8mL), a saturated solution of brine (8mL), dried (Na2SO4) and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired products 2. |
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