Structure of 529-23-7
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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. : | 529-23-7 |
Formula : | C7H7NO |
M.W : | 121.13 |
SMILES Code : | NC1=C(C=O)C=CC=C1 |
MDL No. : | MFCD00007709 |
InChI Key : | FXWFZIRWWNPPOV-UHFFFAOYSA-N |
Pubchem ID : | 68255 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.23 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.98 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.01 |
Solubility | 1.19 mg/ml ; 0.00983 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.09 |
Solubility | 0.995 mg/ml ; 0.00822 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.94 |
Solubility | 1.39 mg/ml ; 0.0115 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) |
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 |
-5.92 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 |
2.0 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) |
1.0 |
* 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 |
---|---|---|
95% | With Nafion NR50; In ethanol; at 200℃; for 1.0h;Microwave irradiation; | General procedure: A mixture of 2-aminobenzophenone 2 (1.0 mmol), ketone 3 or 4 (1.1 mmol), and Nafion NR50 (20 mol%) in ethanol (10 mL) was loaded into a dried 35 mL microwave vial at 25 C. The mixture was subjected to microwave irradiation and stirred at 200 C for 1 h. Consumption of the starting materials was confirmed by TLC. The mixture was cooled to 25 C and then transferred to a 100 mL round-bottom flask; the solvent was concentrated under reduced pressure to afford crude product. The solid crude product was recrystallized (hexane-EtOAc, 5:1 to 2:1). The oily or gummy crude product was purified by column chromatography (silica gel, hexanes-EtOAc, 4:1 to 1:1). This afforded products 1a-ac, 5a-k, and 6a-p. |
64% | With magnesium(II) chloride hexahydrate; In ethanol; at 80℃; for 12.0h;Schlenk technique; | General procedure: A mixture of 2-aminoaryl ketones 1 (0.50 mmol), β-ketoesters/ketones 2 (1.0 mmol), and magnesium chloride (MgCl2 · 6H2O, 20.3 mg, 0.10 mmol) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and the mixture was stirred at 80 C until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography. |
51% | In water; for 5.0h;Reflux; | To compound 6-1 (1.0 g, 8.25 mmol) dissolved in water (20 mL) was added acetylacetone (826 mg, 8.25 mmol) and reacted at reflux for 5 h. When the completion of the reaction was monitored by LC-MS, the reaction solution was poured into ice water, then extracted with ethyl acetate. The organic phases were combined, washed once with saturated aqueous salt solution, dried with sodium sulfate, filtered and concentrated, and purified by column chromatography to obtain the target product 6-2 (780 mg) with a yield of 51%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 20℃; for 4h; | General procedure: Initially, phenol (10 mmol) was dissolved in acetonitrile. Themixture solution was slowly added 3,3-dimethylbutyryl chloride(1.5 equiv) at 0 C, and then stirred at room temperature for 12 h.The solvent was evaporated at reduced pressure. The residue waspurified by silica gel column chromatography using a mixture ofn-hexane and acetone to afford the phenyl pivalate. Subsequently,phenyl pivalate was dissolved in acetonitrile. The mixture solutionwas slowly added chlorosulfonic acid (1.5 equiv) at 0 C andreacted at 0 C for 15 min, and then refluxed at 75 C for 2 h. Thesolutions were quenched by ice; the resulting mixtures were filtrated;and the residues was purified by silica gel column chromatographyusing a mixture of n-hexane/ethyl acetate to afford<strong>[150374-99-5]4-(chlorosulfonyl)phenyl pivalate</strong> (Scheme 1). To a mixture solutionof 2-aminoacetophenone, 1-(2-aminophenyl)propan-1-one,1-(2-aminophenyl)butan-1-one, 1-(2-aminophenyl)pentan-1-one,or 2-aminobenzaldehyde (each 1.0 equiv) in pyridine, respectively,was added <strong>[150374-99-5]4-(chlorosulfonyl)phenyl pivalate</strong>, and then stirred atroom temperature for 4 h. The reaction mixture was concentratedand purified by silica gel column chromatography using a mixtureof n-hexane/acetone solutions, to afford the products (Scheme 2,1-5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: General Procedure for the Synthesis of ArylquinsTo a solution of 2.38 mmol (1.3 equiv) of the appropriate benzyl cyanide in 3 mL of anhydrous DMF at 0C was added 2.38 mmol (1.3 equiv) of potassium tert-butoxide. The mixture was stirred for 15 min, and 1.83 mmol of appropriate 2-aminobenzaldehyde dissolved in 1 mL of anhydrous DMF was added dropwise at 0C. The mixture was warmed to 25C and stirred for 3-4 h at 90C. After cooling the mixture was quenched by pouring into water to afford a precipitate that was collected and purified by recrystallization and/or chromatography as noted for individual compounds described below.3-(2-Fluorophenyl)quinolin-2-amine (Arylquin 8). Purified by chromatography on silica gel using 1:10 methanol-dichloromethane (Rf=0.55): Yield 79%, mp 152-153C.1H NMR (DMSO-d6 [M+H+] -7.44 (m, 4H), 7.37-7.32 (m, 2H), 7.22-7.18 (m, 1H), 6.03 (s, 2H, NH2). 13C NMR (DMSO-d6 G - +] 155.85, 147.59, 137.86, 131.77 (d, J=3.3Hz), 130.36 (d, J=8.0Hz), 129.52, 127.65, 124.95, 124.90, 124.77 (d, J=16.1Hz), 122.80, 121.59, 118.76, 116.11 (d, J=22.2Hz). HRMS (ESI) calcd for C15H12FN2 [MH+]: 239.09790. Found: 239.09831. Anal. Calcd for C15H11FN2: C, 75.62; H, 4.65. Found: C, 72.39; H, 4.71. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With [RuCl2pentamethylcyclopentadiene]n; silver trifluoroacetate; trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 80℃; for 8h; | The preparation method of compound I-25,Including the following process: 0.2mmol of 2-aminobenzaldehyde,<strong>[1006-67-3]5-phenylisoxazole</strong> 0.3mmol,Dichloro (pentamethylcyclopentadienyl) ruthenium () 0.005mmol,Silver trifluoroacetate 0.02mmol,Add 0.2mmol trifluoroacetic acid to the reaction tube,Dissolved in an appropriate amount of trifluoroethanol solvent,React at 80 for 8 hours,The reaction solution was filtered through diatomaceous earth, and the filtrate was concentrated,Purification by column chromatography gave 15.0 mg of the target product with a yield of 33%. |
33% | With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; silver trifluoroacetate; trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 80℃; for 10h; | General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with 2-aminobenzaldehyde 1a (0.1 mmol), isoxazole 2a (0.12 mmol), [Cp*RuCl2]2 (2.5 mol %), CF3COOAg (10 mol %), CF3COOH (1 equiv.) in anhydrous CF3CH2OH (1.5 mL). The reaction mixture was stirred at 80 for 10 h under air atmosphere. When the reaction was completed, the mixture was cooled to room temperature and then purified by column chromatography on silica gel with ethyl acetate/petroleum ether (1:5) to give the desired product 3a. |
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