Structure of 7570-45-8
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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. : | 7570-45-8 |
Formula : | C15H13NO |
M.W : | 223.27 |
SMILES Code : | O=CC1=CC2=C(C=C1)N(CC)C3=C2C=CC=C3 |
MDL No. : | MFCD00004963 |
InChI Key : | QGJXVBICNCIWEL-UHFFFAOYSA-N |
Pubchem ID : | 82055 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 13 |
Fraction Csp3 | 0.13 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 70.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
22.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.95 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.62 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.2 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.15 |
Solubility | 0.0159 mg/ml ; 0.0000713 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.11 |
Solubility | 0.0172 mg/ml ; 0.0000772 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.88 |
Solubility | 0.00293 mg/ml ; 0.0000131 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) |
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 |
-4.86 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.34 |
* 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 potassium hydroxide;Sealed tube; Microwave irradiation; Green chemistry; | General procedure: A mixture of substituted 2-hydroxy acetophenone 1(1.19 ml, 10 mmol), 9-ethyl-9H-carbazol-3-carbaldehyde 2 (2.23 g, 10 mmol) and powdered KOH was taken in aquartz tube and inserted into a Teflon vial with screw capped, and then it was subjected to microwave irradiation at 180 watts for 5-8 min. As indicated by TLC, after completion of reaction, the reaction mixture was poured into ice-cold water and neutralized with dil. HCl. The yellow product formed was filtered and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium hydroxide; In ethanol; at 20℃; for 24h; | General procedure: 9-Ethyl-9H-carbazole-3-carbaldehyde (0.005 mol), substituted o-hydroxy acetophenones (0.005 mol), and 2 gm KOH were dissolved in 15 mLethanol, at room temperature reaction mixture was stirred for 24 h. Completion of the reaction was identified by TLC. Finally, the reaction mixture was poured with crushed ice, acidified with concentrated HCl and the solid obtained was filtered and recrystalized from ethanol afford the target compounds 2(a-d). |
With sodium hydroxide; In ethanol; at 20℃; | General procedure: To a well stirred solution of 2-hydroxyacetophenone 1a-i (1 mmol) and 9-ethyl-9H-carbazole-3-carbaldehyde 2 (1 mmol) in EtOH (20 mL) was added NaOH (4 mmol in 10 mLof EtOH) at room temperature. The reaction mixture was further stirred for 4-5 h. Afterconsumption of reactants (as indicated by TLC), the reaction mixture was dissolved in aqueousNaOH (5 mmol in 5 mL), 3 mL of 30 % H2O2 was added dropwise and the stirring wascontinued for 2-3 h. After completion of reaction (monitored by TLC), the resulting lightyellow reaction mixture was poured onto crushed ice and neutralized with dilute HCl. Thethus-obtained light yellow solid was filtered, washed with water and dried. The crude productwas purified by column chromatography on silica gel using hexane:ethyl acetate (7:3) aseluent to afford the desired products 3a-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydroxide; In ethanol; at 20℃; for 2h; | General procedure: Appropriately substituted acetophenone (1 mmol) and 2a-2i(1 mmol) were dissolved in EtOH (5 mL), 10% NaOH (0.5 mL) wasadded slowly. Then, the solution mixture was stirred at roomtemperature for 2 h. The yellow solid was filtrated. After recrystallizationfrom ethanol, a yellow solid was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 3h;Heating; | General procedure: 9-Ethyl-9H-carbazole-3-carboxaldehyde (0.1 mmol) was reacted with phenyl hydrazine or its derivatives (0.13 mmol) in 20 mL of EtOH for 3 h on the hot water bath. On cooling, the precipitate was collected washed with cold EtOH to give the final compounds with 45-87 % yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 3h;Heating; | General procedure: 9-Ethyl-9H-carbazole-3-carboxaldehyde (0.1 mmol) was reacted with phenyl hydrazine or its derivatives (0.13 mmol) in 20 mL of EtOH for 3 h on the hot water bath. On cooling, the precipitate was collected washed with cold EtOH to give the final compounds with 45-87 % yield. |
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