Structure of 40757-20-8
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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. : | 40757-20-8 |
Formula : | C9H9NO5 |
M.W : | 211.17 |
SMILES Code : | O=C(OC)C1=CC=C(OC)C([N+]([O-])=O)=C1 |
MDL No. : | MFCD00024213 |
Boiling Point : | No data available |
InChI Key : | ZUZYMTBOKNSYEB-UHFFFAOYSA-N |
Pubchem ID : | 602104 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H412 |
Precautionary Statements: | P273 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
81.35 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.8 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.17 |
Solubility | 1.43 mg/ml ; 0.00676 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.89 |
Solubility | 0.273 mg/ml ; 0.00129 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.99 |
Solubility | 2.17 mg/ml ; 0.0103 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 |
No |
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) |
No |
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 |
-6.47 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.05 |
* 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 hydrogen;Raney nickel; In N,N-dimethyl-formamide; under 2585.81 Torr; for 5.0h; | INTERMEDIATE 1; 4-methoxy-acridine-l-carboxyIic acid; STEP 1: Methyl-(3-amino-4-methoxy) benzoate; Methyl (4-methoxy-3-nitro)benzoate (4.2 g, 0.019 mol) (Lancaster) was dissolved in DMF (65 ml) and hydrogenated in the presence of Raney nickel (2.1 g) for 5 h at 50 psi. The reaction mixture was filtered through celite. Water (100 ml) was added to the filtrate to precipitate the product. The precipitated product was extracted in dichloromethane, dried over anhydrous sodium sulphate, and concentrated in vacuo to obtain the product as a buff color solid (3.4 g).IR (KBr): 3297, 2949, 2846, 1710, 1600, 1517, 1440, 1310, 1219, 1198, 1106, 1021, 876, 761 cm"1. H*-NMR (300 MHz, DMSOd6) delta 3.76 (s, 3 H), 3.82 (s, 3 H), 4.99 (brs, 2 H, exchanges with D2O), 6.87 (d, 1 H, J = 8.4 Hz), 7.21 (d, 1 H, J = 8.2 Hz), 7.26 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sulfuric acid;Reflux; | General procedure: To a solution of 6-bromopicolinic acid (50.0 g, 248 mmol) in methanol (350 mL) was added concentrated sulfuric acid (5 mL) dropwise at it After the addition, the mixture was heated to reflux until the reaction was completed, the solvent was distilled off in vacuo and the residue was diluted with water (300 mL). The system was adjusted with saturated sodium bicarbonate aqueous solution to weakly alkaline. The resulting mixture was extracted with EtOAc (200 mL x 2), and the combined organic layers were dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated to give the title compound as a white solid (51.5 g, 96%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Yield of methyl 4-methoxy-3-nitrobenzoate: 44.3 g (91.3%, based on 4-hydroxy-3-nitrobenzoic acid employed). The total yield of methyl 4-methoxy-3-nitrobenzoate and 4-methoxy-3-nitrobenzoic acid, based on the mixture of 4-hydroxy- and 4-methoxy-3-nitrobenzoic acid employed, is 95.8%. Pure substance content: 100% (GC) Melting point: 107 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step j. Methyl 3-nitro-4-chlorobenzoate (COMPOUND XIII) (see above for synthesis of 4-chloro-anti-CG) (1 equivalent) is treated with sodium methoxide (1.1 equivalent) in methanol with heating to produce the methyl 3-nitro-4-methoxybenzoate (COMPOUND XIV) which is purified by column chromatography and/or crystallization. |
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