Structure of 51677-09-9
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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. : | 51677-09-9 |
Formula : | C11H9NO3 |
M.W : | 203.19 |
SMILES Code : | O=C(C1=NOC(C2=CC=CC=C2)=C1)OC |
MDL No. : | MFCD02159553 |
InChI Key : | XMPLCJOQBDGMKT-UHFFFAOYSA-N |
Pubchem ID : | 905953 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.09 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.29 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.13 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.33 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.15 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.18 |
Solubility | 0.133 mg/ml ; 0.000656 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.51 |
Solubility | 0.0622 mg/ml ; 0.000306 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.84 |
Solubility | 0.0295 mg/ml ; 0.000145 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 |
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 |
-5.58 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) |
2.76 |
* 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 |
---|---|---|
81% | With silver tetrafluoroborate; phenol In tetrahydrofuran for 12 h; Reflux | General procedure: To a solution of alkynyl oxime ether 1 (0.15 mmol) in THF (5 mL) were added phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol), with a drying tube filled with silica gel at room temperature. After being stirred at reflux for 1-12 h (TLC monitoring), the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/AcOEt=3-10:1) to afford isoxazole 3. The physical and spectroscopic data of 3a5 and 3j12h were in accord with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With triethylamine In diethyl ether at 20℃; for 9.5 h; Inert atmosphere | To a stirred solution of methyl chlorooximidoacetate (235 mg, 1.71 mmol) and phenylacetylene (0.38 mL, 3.42 mmol) in Et2O (8.55 mL) was added Et3N (0.47 mL, 3.42 mmol) at rt under N2 and the resultingsolution was stirred for 9.5 h. Sat. NH4Cl aq. was added to the reaction mixture and the resultingsolution was extracted with AcOEt. The combined organic layer was dried over Na2SO4 andconcentrated in vacuo. The crude product was purified by flash column chromatography on silica gel(hexane/AcOEt = 5/1). The product was obtained as pale yellow oil (108 mg, 31percent); |
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