Structure of 38186-51-5
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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. : | 38186-51-5 |
Formula : | C11H16BrO3P |
M.W : | 307.12 |
SMILES Code : | BrC1=CC=C(C=C1)CP(OCC)(OCC)=O |
MDL No. : | MFCD05663693 |
InChI Key : | IPTXXSZUISGKCJ-UHFFFAOYSA-N |
Pubchem ID : | 11077666 |
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 | 6 |
Fraction Csp3 | 0.45 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.17 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.34 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.65 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.02 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.24 |
Solubility | 0.175 mg/ml ; 0.000569 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.17 |
Solubility | 0.208 mg/ml ; 0.000676 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.72 |
Solubility | 0.00581 mg/ml ; 0.0000189 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 |
-6.35 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 |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.33 |
* 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 |
---|---|---|
82% | With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere; | <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (3 52 g, 13 mmol) was reacted with (diethyl 4-bromobenzyl) phosphonate (4 42 g, 14.4 mmol) was placed In a two-necked flask, evacuate and pass nitrogen and add 20 m of anhydrous tetrahydrofuran (THF). Under ice bath, potassium tert-butoxide (t-BuOK X 3.36 g, 30 mmol) dissolved in THF (30 mL) Add slowly to the mixture at 0 C for 15 minutes. The solvent was removed by concentration under reduced pressure and the column was reused (N-hexane: dichloromethane = 5: 1) to give the white intermediate 1-4 ((E) -3- (4-bromostyryl) -9-phenyl-9H-carbazole) (4.52 g, yield 82%). |
63% | With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere; | <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (3.52 g, 13 mmol) and diethyl 4-bromobenzyl phosphonate (4.42 g, 14.4 mmol) was added to a solution placed in a two-necked flask, evacuated and passed through nitrogen, 20 m L of anhydrous tetrahydrofuran (THF) was added; Potassium tert-butoxide (t-BuOK) (3.36 g, 30 mmol) dissolved in THF (30 mL) was added slowly under ice-cooling, Reaction at 0 C for 15 minutes. The solvent was removed by concentration under reduced pressure and purified by column chromatography (n-hexane: dichloromethane = 5: 1) to give a white intermediate I-4 ((E) -3- (4-bromostyryl) -9-phenyl-9H-carbazole) (4.52 g, yield 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere; | Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of 4- (9H-carbazol-9-yl) benzaldehyde (0.27 g, 1 mmol) and diethyl 4-bromobenzylphosphate (diethyl Bromobenzyl phosphonate (0.34 g, 1.1 mmol) was placed in a single neck flask and 3 mL of anhydrous tetrahydrofuran was added under a nitrogen atmosphere. The solution in the flask was slowly added to the two-necked flask under ice-cooling and mixed and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was filtered and the intermediate product I-5 ((E) -9- (4- (4-bromostyryl) phenyl) -9H-carbazole was obtained by repeatedly washing with methanol to obtain a pale yellow powder. (0.39 g, yield 93%). |
93% | With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere; | Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (0.27 g, 1 mmol) and diethyl 4-bromobenzyl phosphonate (0.34 g, 1.1 mmol) placed in a single neck flask, in the nitrogen environment by adding 3mL of anhydrous tetrahydrofuran. The solution in the flask was slowly added to the flask and mixed under ice bath and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was evacuated and filtered, and repeatedly washed with methanol to obtain the intermediate product of the pale yellow powder I-5 ((E)-9-(4-(4-bromostyryl)phenyl)-9H-carbazole (0.39 g, yield 93%). |