Structure of 56469-02-4
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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. : | 56469-02-4 |
Formula : | C9H9NO2 |
M.W : | 163.17 |
SMILES Code : | OC1=CC=CC2=C1CCNC2=O |
MDL No. : | MFCD02258901 |
InChI Key : | CMNQIVHHHBBVSC-UHFFFAOYSA-N |
Pubchem ID : | 13236663 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 48.23 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.24 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.78 |
Solubility | 2.73 mg/ml ; 0.0167 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.5 |
Solubility | 5.16 mg/ml ; 0.0316 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.58 |
Solubility | 0.426 mg/ml ; 0.00261 mol/l |
Class? Solubility class: Log S scale |
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 |
No |
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) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
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 |
-6.67 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) |
1.47 |
* 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 |
---|---|---|
5.3 g (89%) | With dimethyl sulfate; In methanol; sodium hydroxide; water; | EXAMPLE V 3,4-Dihydro-5-methoxy-1(2H)-isoquinolinone To a refluxing solution of 5.5 g (33.7 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone in 35 ml of 2N NaOH and 70 ml of methanol was added 4 ml of dimethyl sulfate. At two-hour intervals additional amounts of NaOH and dimethyl sulfate were added and the reaction was heated under reflux conditions overnight. The mixture was concentrated, diluted with 300 ml of water, and acidified (pH 2-3) with concentrated sulfuric acid. The solid which formed was collected and dried to give 5.3 g (89%) of material sufficiently pure for the next step. An analytical sample was obtained by recrystallization from acetone; mp 147-149. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate Q5-Methoxy-3,4-dihydro-2H-isoquinolin-1 -oneTo a stirring solution of 5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (200 mg, 1.226 mmol) in DMF (8 ml) was added Cs2C03 (599 mg, 1.839 mmol). The reation mixture was left to stir for 20 minutes at 50 C and then treated with methyl iodide (0.115 ml, 1.839 mmol). After stirring at 50 C for 30 min, the mixture was diluted with EtOAc water. The organic portion was separated and washed with water, brine, dried (MgS04) and concentrated in vacuo to afford the title compound as a pale yellow solid; LC-MS Rt =1.08 mins; MS m/z 178.1 [M+H]+; Method 2minLC_v002. |
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