Structure of 723281-72-9
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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. : | 723281-72-9 |
Formula : | C9H4BrClN2O2 |
M.W : | 287.50 |
SMILES Code : | O=[N+](C1=C(Cl)C2=CC(Br)=CC=C2N=C1)[O-] |
MDL No. : | MFCD09909913 |
InChI Key : | KHKPVEMMXJCWGP-UHFFFAOYSA-N |
Pubchem ID : | 21984128 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.28 |
TPSA ? Topological Polar Surface Area: Calculated from |
58.71 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.75 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.6 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.15 |
Solubility | 0.0202 mg/ml ; 0.0000701 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.25 |
Solubility | 0.0162 mg/ml ; 0.0000562 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.54 |
Solubility | 0.00823 mg/ml ; 0.0000286 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 |
-5.68 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 |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.02 |
* 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 |
---|---|---|
100% | With triethylamine; In dichloromethane; at 20℃; for 2.5h; | (XIX) Scheme XIX Intermediate 432: 3-(6-bromo-3-nitroquinolin-4-yl)aminocyclopentanol 1.69 g (5.9 mmol) of Compound 3 and 1.226 g (8.9 mmol) of <strong>[1184919-69-4]3-aminocyclopentanol hydrochloride</strong> (a mixture of cis and trans isomers) were dissolved in 20 ml of dichloromethane, added with 3.3 ml (23.6 mmol) of triethylamine, stirred at room temperature for 2.5 h to precipitate out solids, filtered, washed with a small amount of dichloromethane, and pumped to dryness to afford a yellow solid (2.154 g). Yield: 100%. LC-MS: 351.8, 353.8 [M+1]+, tR = 1.822 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 460: 4-((6-bromo-3-nitroquinolin-4-yl)amino)-1-methylcyclohexanol 0.5 g (2.6 mmol) of Intermediate 459 and 0.86 g (8.5 mmol) of triethylamine were added into 20 ml of dichloromethane, stirred for 10 min, and then added with 0.5 g (1.7 mmol) of Intermediate 3, and stirred at room temperature overnight. The reaction solution was evaporated to dryness and purified by passing through a silica gel column, and collected two product fractions, to afford 170 mg of yellow solid (a mixture of cis and trans isomers). LC-MS: 380,382 [M+1]+, tR = 2.036&2.107 min. |
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