Structure of 475994-60-6
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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.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 475994-60-6 |
| Formula : | C9H6BrNO |
| M.W : | 224.05 |
| SMILES Code : | C1=CC2=C(C(=C1)Br)C(=NC=C2)O |
| English Name : | 8-Bromoisoquinolin-1(2H)-one |
| MDL No. : | MFCD11858429 |
| InChI Key : | NQMZAFRCYDJSEU-UHFFFAOYSA-N |
| Pubchem ID : | 52987747 |
| Num. heavy atoms | 12 |
| Num. arom. heavy atoms | 10 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 51.47 |
| TPSA ? Topological Polar Surface Area: Calculated from |
33.12 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.93 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.77 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.7 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.31 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.64 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.47 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-3.59 |
| Solubility | 0.0575 mg/ml ; 0.000257 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.12 |
| Solubility | 0.17 mg/ml ; 0.000757 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.98 |
| Solubility | 0.0232 mg/ml ; 0.000104 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 |
-5.7 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) |
1.59 |
* 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 |
|---|---|---|
| 94% | With potassium carbonate In DMF (N,N-dimethyl-formamide) for 72h; | 26.c (c) [8-BROMO-2-METHYL-2H-ISOQUINOLIN-1-ONE] A solution of (b) [(180 MG,] 0.8 mmol) [IN DMF] (5 ml) was treated with potassium carbonate (140 mg) and methyl iodide (0.062 ml) and stirred for 3 days then evaporated. The residue was partitioned between dilute aqueous sodium chloride solution and dichloromethane, re-extracting with dichloromethane twice more. The combined organic extracts were dried and evaporated affording a yellow solid (180 mg, 94%). MS (+ve ion electrospray) m/z 239 (MH+) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 150 mg | With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 56.1 Step 1: Synthesis of 8-bromo-2-methylisoquinolin-4(2H)-one (Intermediate 57-2) The starting material 57-1 (1g, 4.464mmol) was dissolved in N,N-dimethylformamide (20mL) at room temperature, potassium carbonate (1.8g, 13.043mmol) was added, and iodomethane (2g, 14.084mmol), stirred and reacted at 50°C for 12h, water (30mL) was added to the reaction solution, the mixture was extracted with dichloromethane (30mLX3), the organic phases were combined, dried and filtered with anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to obtain The title compound (150mg). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Compound 164 Compounds Synthesized by Method E Compound 164 To a pressure vessel containing 8-bromo-2H-isoquinolin-1-one (1.00 g, 4.46 mmol), Copper (I) iodide (90 mg, 472 μmol) and L-Proline (104 mg, 903 μmol) was added concentrated ammonium hydroxide (25 mL). The vessel was capped and stirred at 110° C. for 18 h. The mixture was cooled to RT, concentrated to dryness and the residue purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to provide 8-amino-2H-isoquinolin-1-one (632 mg) as a greenish-gray solid. ESI-MS: m/z 161.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 10.76 (br s, 1H), 7.37-7.13 (m, 3H), 6.93 (dd, J=7.1, 5.8 Hz, 1H), 6.56 (dd, J=7.7, 1.2 Hz, 1H), 6.51 (dd, J=8.1, 1.1 Hz, 1H), 6.27 (dd, J=7.1, 1.5 Hz, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 632 mg | With ammonium hydroxide; copper(l) iodide; <i>L</i>-proline at 110℃; | To a pressure vessel containing 8-bromo-2H-isoquinolin-1-one (1.00 g, 4.46 mmol), Copper (I) iodide (90 mg, 472 μmol) and L-Proline (104 mg, 903 μmol) was added concentrated ammonium hydroxide (25 mL). The vessel was capped and stirred at 110° C. for 18 h. The mixture was cooled to RT, concentrated to dryness and the residue purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to provide 8-amino-2H-isoquinolin-1-one (632 mg) as a greenish-gray solid. ESI-MS: m/z 161.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 10.76 (br s, 1H), 7.37-7.13 (m, 3H), 6.93 (dd, J=7.1, 5.8 Hz, 1H), 6.56 (dd, J=7.7, 1.2 Hz, 1H), 6.51 (dd, J=8.1, 1.1 Hz, 1H), 6.27 (dd, J=7.1, 1.5 Hz, 1H). |
| 632 mg | With ammonium hydroxide; copper(l) iodide; <i>L</i>-proline at 110℃; | To a pressure vessel containing 8-bromo-2H-isoquinolin-1-one (1.00 g, 4.46 mmol), Copper (I) iodide (90 mg, 472 μmol) and L-Proline (104 mg, 903 μmol) was added concentrated ammonium hydroxide (25 mL). The vessel was capped and stirred at 110° C. for 18 h. The mixture was cooled to RT, concentrated to dryness and the residue purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to provide 8-amino-2H-isoquinolin-1-one (632 mg) as a greenish-gray solid. ESI-MS: m/z 161.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 10.76 (br s, 1H), 7.37-7.13 (m, 3H), 6.93 (dd, J=7.1, 5.8 Hz, 1H), 6.56 (dd, J=7.7, 1.2 Hz, 1H), 6.51 (dd, J=8.1, 1.1 Hz, 1H), 6.27 (dd, J=7.1, 1.5 Hz, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 632 mg | With ammonium hydroxide; copper(l) iodide; <i>L</i>-proline at 110℃; Sealed tube; | To a pressure vessel containing 8-bromo-2H-isoquinolin-1-one (1.00 g, 4.46 mmol), Copper (I) iodide (90 mg, 472 μmol) and L-Proline (104 mg, 903 μmol) was added concentrated ammonium hydroxide (25 mL). The vessel was capped and stirred at 110° C. for 18 h. The mixture was cooled to RT, concentrated to dryness and the residue purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to provide 8-amino-2H-isoquinolin-1-one (632 mg) as a greenish-gray solid. ESI-MS: m/z 161.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 10.76 (br s, 1H), 7.37-7.13 (m, 3H), 6.93 (dd, J=7.1, 5.8 Hz, 1H), 6.56 (dd, J=7.7, 1.2 Hz, 1H), 6.51 (dd, J=8.1, 1.1 Hz, 1H), 6.27 (dd, J=7.1, 1.5 Hz, 1H). |

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