Structure of 16619-14-0
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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. : | 16619-14-0 |
Formula : | C15H13NO |
M.W : | 223.27 |
SMILES Code : | C1(=CC=CC=C1)C3CC(C2=CC=CC=C2N3)=O |
MDL No. : | MFCD00098918 |
InChI Key : | PUCZUBFZQVSURB-UHFFFAOYSA-N |
Pubchem ID : | 10889522 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.13 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 71.25 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.92 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.53 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.52 |
Solubility | 0.0674 mg/ml ; 0.000302 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.19 |
Solubility | 0.143 mg/ml ; 0.000642 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.46 |
Solubility | 0.000772 mg/ml ; 0.00000346 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) |
Yes |
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) |
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) |
Yes |
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 |
-5.59 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) |
2.31 |
* 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 |
---|---|---|
85% | With iodine; In dimethyl sulfoxide; at 80℃; for 12h; | General procedure: A mixture of 2 (1 mmol) and iodine (1.5 mmol) inDMSO was warmed at 80°C in an oil bath for 12 hours. On completion of the reaction, the reaction mixture was poured onto saturated solution of sodium thiosulfate. The precipitated solid was collected and the desired product was purified by column chromatography using silica gel (60x120 mesh) with increasing percentage of ethyl acetate in hexaneas eluting solvent. The physical data of compounds are provided below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With zirconyl(IV) nitrate hydrate; In ethanol; water; at 50℃; for 3h;Green chemistry;Catalytic behavior; | General procedure: A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 molpercent) washeated with stirring at 50 °C while the progress of the reactionwas monitored by TLC. The reaction was then quenched withH2O (5 mL), and the mixture was extracted with Et2O (3 × 10mL). The combined organic extracts were washed with brine (5mL) then dried (Na2SO4), filtered, and concentrated underreduced pressure. The crude product was purified by columnchromatography [silica gel, hexane?EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry1)5b,6b,11Off-white solid; yield: 218 mg (98percent); mp 153?155 °C. IR (KBr):3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,974, 861 cm?1. 1H NMR (600 MHz, CDCl3): delta = 7.83 (dd, J = 8.5,1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40?7.36 (m, 2 H), 7.35?7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150MHz, CDCl3): delta = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With hydrogenchloride; In water; for 12h;Reflux; | General procedure: A mixture of 1 (1 mmol) and 5percent HCl (10 ml) was refluxed for 12 hours. The reaction mixture was kept at room temperature and then basified with NH4OH. The precipitated solid was filtered sand recrystallized from ethanol. The physical data for the characterstic compound is shown below |
4.75 g | With hydrogenchloride; In ethanol; water; for 8h;Reflux; | 7.9 g (0.03 mol) of (E)-N-[2-(3-phenylacryloyl)phenyl]acetamide (C1) was dissolved in 80 ml of ethanol. Add 40 ml of 5percent hydrochloric acid and reflux for 8 h. The reaction solution was poured into 200 ml of ice water, and the pH was adjusted to 9 with aqueous ammonia to precipitate a large amount of white solid. Filtering, ethanol recrystallization, 2-phenyl-2,3-dihydro-4(1H)-quinolinone (D1) is obtained as a white solid. The yield is 4.75g, the yield is 71.1percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With C26H18N2O12Ti; In methanol; at 20℃; for 26h; | General procedure: 1.2 mmol of 2-aminoacetophenone and 1.0 mmol of aromatic aldehyde were added to 2 mL of methanol. The reaction was carried out for 26 hours at room temperature, and the results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium tetrahydroborate; In methanol; at 0 - 5℃; for 3h; | To a suspension of 2-phenyl-l,2,3,4-tetrahydiO-4-quinolones (223mg, 1 mmol) in dry methanol (10 mL) is added NaBH4 (4 mmol) and the reaction mixture stirred at 0-50C under nitrogen atmosphere for 3 hr. The reaction mixture is concentrated under reduced pressure and 2M aqueous hydrochloric acid (~2mL) is added to adjust the pH 6. This solution is extracted into diethyl ether (20 mL), washed with water (2 x 15 mL), dried over NaSO4 and concentrated under reduced pressure to give required product. Yield 210 mg (93percent); IR (KBR) 3304, 1453, 1209 cm"1; MS m/z 226.1 (M+H)+. |
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