Structure of 5153-67-3
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 5153-67-3 |
Formula : | C8H7NO2 |
M.W : | 149.15 |
SMILES Code : | [O-][N+](=O)\C=C\C1=CC=CC=C1 |
MDL No. : | MFCD00007402 |
InChI Key : | PIAOLBVUVDXHHL-VOTSOKGWSA-N |
Pubchem ID : | 5284459 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.56 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.83 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.98 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.37 |
Solubility | 0.643 mg/ml ; 0.00431 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.7 |
Solubility | 0.296 mg/ml ; 0.00198 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.85 |
Solubility | 2.11 mg/ml ; 0.0142 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 |
-5.71 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) |
2.36 |
* 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 |
---|---|---|
With iodine; In diethyl ether; at 20 - 50℃; for 136h; | To a stirred suspension of (E)-(2-nitrovinyl)benzene (350 mg, 2.347 mmol) in Et20 (2 mL) was added 5 -methyl- lH-indazole (700 mg, 5.30 mmol) and iodine (596 mg, 2.347 mmol). The reaction mixture was stirred at room temperature for 5 days. LCMS showed the product. The reaction was heated at 50°C for 16 h. The mixture was quenched with water, washed with a mix of saturated sodium thiosulfate/NaHCOs (aq) (4/1) solution, extracted with DCM (100 mL><2). The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography on silica gel Biotage 25M, eluting with 0, 2, 5,10 and 15percent EtOAc in Hexanes to give regioismer A (5-methyl-l-(2-nitro-l-phenylethyl)-lH- indazole) and regioisomer B (5-methyl-2-(2-nitro-l-phenylethyl)-2H-indazole). Step A, regioisomer A, LCMS calc. = 282.12, found = 282.05 (M+H)+. Step A, regioisomer B, LCMS calc. = 282.12, found = 282.04 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In water; at 90℃; for 10h;Green chemistry; | Typically, <strong>[1194-22-5]2-methylpyrimidine-4,6-diol</strong> (1b, 0.5 mmol, 1.0 equiv) was introduced into a 10 mL reaction vial, (E)-(2-nitrovinyl)benzene (2a, 0.5 mmol, 1.0 equiv), as well as water (2.5 mL). Then, the reaction vial was closed and stirred for given time at 90 C in 10 hours. Upon completion, the reaction mixture was cooled to room temperature and diluted with cold water (30 mL). The solid product was collected by filtration and was purified by recrystallization from hot 95% EtOH to afford the goal product 2-methyl-5-(2-nitro-1-phenylethyl)pyrimidine-4,6-diol (6) as off-white solid. |
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