Structure of 168770-44-3
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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. : | 168770-44-3 |
Formula : | C7H7FN2O2 |
M.W : | 170.14 |
SMILES Code : | CC1=C(N)C=C(F)C=C1[N+]([O-])=O |
MDL No. : | MFCD08690074 |
InChI Key : | XWXBFFACZMFPHH-UHFFFAOYSA-N |
Pubchem ID : | 18465377 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P264-P270-P301+P312-P330 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 44.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
71.84 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.19 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.53 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.05 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.16 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.13 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.16 |
Solubility | 1.17 mg/ml ; 0.00687 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.65 |
Solubility | 0.383 mg/ml ; 0.00225 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.08 |
Solubility | 1.42 mg/ml ; 0.00832 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) |
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 |
-6.25 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 |
3.0 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) |
2.01 |
* 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 |
---|---|---|
65% | With sodium sulfide In ethanol; water at 25℃; for 4.5 h; | To a solution of K101-b (9.0 g, 45.0 mmol) in EtOH (100 mL), a solution of Na2S (16.2 g, 67.5 mmol) in H2O(50 mL) was added dropwise over 30min at 25°C. The mixture was stirred for 4 hours, then concentrated to afford acrude product. The crude product was diluted with H2O (200 mL) and extracted with EtOAc (100 mL x 2), the combinedorganic layer was dried over anhydrous Na2SO4, filtered and concentrated, the residue was purified by chromatographycolumn (PE/EtOAc=10/1) to afford the product K101-c (5.0 g, 65 percent).1H NMR (DMSO-d6, 300 MHz): δ 6.84 (dd, J = 6.3, 1.8 Hz, 1H), 6.68 (dd, J = 8.4, 1.8 Hz, 1H), 5.90 (br s, 2H), 2.03 (s, 3H). |
60.4% | With hydrogenchloride; iron In 1,4-dioxane; methanol; water at 80℃; for 3 h; Cooling with ice | The starting material 4b (200mg, 1mmol) in methanol (5mL) 1,4-dioxane (2.5 mL) was dissolved,10N HCl (1 mL) Fe (41.9 mg, 3 mmol) was added under ice-cooling, and the mixture was stirred at 80 ° C for 3 h.TLC showed the starting material to react completely.Finally, 42 mg of pale yellow powder was obtained, yield: 60.4percent. |
60.4% | With hydrogenchloride; iron In methanol; hexane; water at 80℃; for 3 h; | The starting material 2a (200 mg, 1 mmol) was dissolved in methanol (5 mL) hexanes (2.5 mL). 10N HCl (1 mL) Fe (41.9 mg, 3 mmol) was added under ice bath. After the addition, stirring at 80 ° C for 3 h, TLC showed that the starting material was completely reacted. Finally, 42 mg of pale yellow powder was obtained, yield: 60.4percent. |
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