Structure of 34658-66-7
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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. : | 34658-66-7 |
Formula : | C13H9BrN2 |
M.W : | 273.13 |
SMILES Code : | BrC1=CC=C(C2=CN3C=CC=CC3=N2)C=C1 |
MDL No. : | MFCD00218250 |
InChI Key : | GRZUOGFRIHABDK-UHFFFAOYSA-N |
Pubchem ID : | 623416 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 15 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 68.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.59 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.76 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.93 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.42 |
Solubility | 0.0103 mg/ml ; 0.0000378 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.64 |
Solubility | 0.0626 mg/ml ; 0.000229 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.45 |
Solubility | 0.00096 mg/ml ; 0.00000352 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) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
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 |
-5.42 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 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.14 |
* 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 |
---|---|---|
71% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 6h;Heating / reflux; | Synthesis of Compound 1; 1.85 g of Intermediate 1c (3.90 mmol) and 1 g of Intermediate 1d (3.90 mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture while the mixture was stirred, and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered while being washed with water, ethanol and THF to obtain 1.73 g of Compound 1 in the form of a pale yellow powder (yield 71%). (1H NMR (400 MHz, CDCl3) 8.13-8.04 (7H), 8.01 (1H), 7.97-7.92 (4H), 7.86-7.82 (2H), 7.75 (2H), 7.71-7.58 (10H), 7.32 (2H), 7.15 (1H), 6.75 (1H)). |
71% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 6h;Heating / reflux; | Synthesis of Compound 1; 1.85 g of Intermediate 1c (3.90 mmol) and 1 g of Intermediate 1d (3.90 mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture while the mixture was stirred, and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered while being washed with water, ethanol and THF to obtain 1.73 g of Compound 1 in the form of a pale yellow powder (yield 71%). (1H NMR (400MHz, CDCl3) 8.13-8.04 (7H), 8.01 (1H), 7.97-7.92 (4H), 7.86-7.82 (2H), 7.75 (2H), 7.71-7.58 (10H), 7.32 (2H), 7.15 (1H),6.75(1H)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With 18-crown-6 ether; potassium carbonate;copper; In 1,2-dichloro-benzene; at 200℃; for 48h;Inert atmosphere; | Into a reactor, 6.1 g (19 mmoles) of <strong>[56525-79-2]3,6-diphenylcarbazole</strong>, 6.3 g (23 mmoles) of Intermediate Compound (A), 0.2 g of copper powder, 1.7 g of 18-crown-6 and 2.9 g (21 mmoles) of potassium carbonate were placed and 30 ml of o-dichlorobenzene was added as the solvent. The resultant mixture was heated at 200° C. in a silicone oil bath under a nitrogen stream and the reaction was allowed to proceed for 48 hours. After the reaction was completed, the reaction mixture was filtered under suction before being cooled and the obtained filtrate was concentrated using an evaporator. To the obtained oily product, 30 ml of methanol was added. The formed solid substance was separated by filtration under a reduced pressure and a gray solid substance was obtained. The obtained solid substance was recrystallized from benzene and 3.0 g (the yield: 31percent) of white crystals were obtained. It was confirmed by 90 MHz 1H-NMR and FD-MS (the field desorption mass analysis) that the obtained crystals were the target substance (A5). The result of the measurement by FD-MS is shown in the following:FD-MS calcd. for C37H25N3=511; found: m/z=511 (M+, 100) |
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