Structure of 642-31-9
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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. : | 642-31-9 |
Formula : | C15H10O |
M.W : | 206.24 |
SMILES Code : | O=CC1=C2C=CC=CC2=CC2=CC=CC=C12 |
MDL No. : | MFCD00001254 |
InChI Key : | YMNKUHIVVMFOFO-UHFFFAOYSA-N |
Pubchem ID : | 69504 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 14 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 66.84 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.16 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.0 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.36 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.21 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.51 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.22 |
Solubility | 0.0124 mg/ml ; 0.0000602 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.06 |
Solubility | 0.0179 mg/ml ; 0.000087 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.7 |
Solubility | 0.000409 mg/ml ; 0.00000198 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) |
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 |
-4.72 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<2.0 |
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 |
---|---|---|
70% | In methanol; at 60℃; for 2h; | A mixture of <strong>[1671-88-1]4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole</strong> (0.25 g, 0.001 mol) and 9-anthraldehyde (0.20g, 0.001 mol) was refluxed for 2h. The formation of yellow precipitate was filtered, washed with cold methanol and then recrystallized from hot ethanol. Yield: 0.3 g (70%), FT-IR, cm-1(KBr disc): 2875 [s, ν(C-H)], 1628 [vs ν(CH=N)], (br, broad; s, strong; vs very strong). Anal. Calc. for C27H18N6: C, 76.04; H, 4.25; N, 19.71. Found: C, 76.10; H, 4.32; N, 19.62%. EI-MS: 427.12 (M+H+). |
54% | With acetic acid; In methanol; at 85℃; for 6h; | 1.20 mmol of 9-anthracenecarbaldehyde and 1.00 mmol of 3,5-dipyridyl-4-amino-1,2,4-triazole are added to 100 ml of a three neck round bottom flask containing 20 ml of methanol.Under magnetic stirring,Slowly heated to 85 C,When all the ingredients are completely dissolved,Slowly add 3 drops of glacial acetic acid.The reaction was stopped after stirring for 6h at 85 C.The resulting reaction solution was cooled to room temperature,That is, yellow precipitate precipitation,filter,Washed three times with methanol,After drying that is L2,Yield 54%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation; | General procedure: A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized to give compounds 3-29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol; for 0.5h; | The ligand (L; anthracene-9-carboxaldehydebenzoicacidhydrazone)was synthesized by dropwise additionof a methanolic solution (7 ml) of 9-anthracenealdehyde(0.041 g. 0.2 mmol) to a methanolic solution (7 ml) of <strong>[33906-30-8]2-hydrazinobenzoic acid hydrochloride</strong> (0.038 g. 0.2 mmol) withstirring for 30 min at room temperature (25 C). The brightyellow color solution was filtered and the solvent was evaporatedby rotary evaporator to obtain a bright yellow compound.Yield: 92%. 1H NMR (400 MHz,DMSO-d6): delta ppm 11.628 (s,1H), 9.321 (s, 1H), 8.797 (m, 1H), 8.775 (m, 1H), 8.639 (s,1H), 8.141-7.542 (m, 9H), 6.871 (m, 1H), 6.853 (m, 1H)[Fig. S1]. 13C NMR (400 MHz, DMSO-d6): delta ppm 169.87,147.45, 139.68, 135.16, 131.85, 131.48, 129.79, 129.29,128.78, 127.17, 126.79, 125.92, 125.62, 118.41, 113.40,110.66 [Fig. S2]. FTIR (KBr pellets, cm-1): 3356, 3065,2921, 2899, 1950, 1734, 1699, 1661, 1597, 1463, 1350,1319, 1306, 1285, 1205, 1170, 1156, 1113, 1094, 1060,1037, 965, 933, 817, 809, 788, 737, 708, 693, 632, 622, 573,496 [Fig. S3]. UV-Vis (DMSO/H2O, 2:1; pH, 7.0): lambdamax (nm)(epsilon, M-1 cm-1): 320 (22,100), 418 (33,000). Mass: m/z (ESI)[M] 340.12 (calculated 340.37) (Scheme 1) [M+H]+ 341.12(calculated 341.38) [Fig. S4]. Emission: lambdaex, 380 nm(isosbestic) and lambdaem, 455 nm. Quantum yield (phi): 0.008. |