Structure of 349-76-8
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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. : | 349-76-8 |
Formula : | C9H7F3O |
M.W : | 188.15 |
SMILES Code : | C1=C(C=CC=C1C(C)=O)C(F)(F)F |
MDL No. : | MFCD00000391 |
Boiling Point : | No data available |
InChI Key : | ABXGMGUHGLQMAW-UHFFFAOYSA-N |
Pubchem ID : | 67682 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H227-H315-H319-H335 |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.82 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.18 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.9 |
Solubility | 0.238 mg/ml ; 0.00126 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.68 |
Solubility | 0.393 mg/ml ; 0.00209 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.62 |
Solubility | 0.045 mg/ml ; 0.000239 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 |
-5.55 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 |
2.0 |
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) |
1.25 |
* 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 |
---|---|---|
42% | With iodine; toluene-4-sulfonic acid hydrazide; In dimethyl sulfoxide; at 100℃; for 6h; | To a dimethylsulfoxide (4 mL) solution of 3'-(trifluoromethyl)acetophenone (400 mg, 2.1 mmol), 2-ethylsulfanylaniline (390.9 mg, 2.6 mmol), 4-methylbenzene sulfonhydrazide (593.9 mg, 3.2 mmol), and iodine (809.4 mg, 3.2 mmol) were sequentially added, followed by stirring at 100 C. for 6 hours. Water was poured in the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% sodium thiosulfate solution and then with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:6) to afford the title compound (yielded 315.5 mg, yield: 42%) as a tan oily product. 1HNMR Spectrum (CDCl3) sigma: 8.24 (1H, s), 8.18 (1H, s), 8.14 (1H, d, J=7.3 Hz), 7.64-7.59 (2H, m), 7.55-7.47 (3H, m), 7.39 (1H, td, J1=7.4 Hz, J2=1.5 Hz), 2.83 (2H, q, J=7.3 Hz), 1.24 (3H, t, J=7.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With iodine; In dimethyl sulfoxide; at 20 - 110℃; for 2h; | Dissolve 3mL of m-trifluoromethylacetophenone in 10mLIn DMSO,Slowly add 2.5g iodine,Add 3.3g at room temperature with stirring<strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> dissolved in 20mLa solution of DMSO,The reaction was carried out at 110 C for 2 h.The reaction system was added with 150 mL of water.Extracted with (3 x 60 mL) ethyl acetate.Reuse (2 × 40mL)Washing with saturated NaHSO3 solution to remove iodine,After washing with water, dry with anhydrous magnesium sulfate,Evaporate the solvent under reduced pressure.The residue was separated on a chromatographic column (eluent: ethyl acetate: petroleum ether = 1:2).2-(3-trifluoromethylbenzoyl)-6-nitro-4(3H)-quinazolinone 4.1 g,Yield 63%,Melting point 172-175 C. |
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