Structure of 5437-99-0
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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. : | 5437-99-0 |
Formula : | C9H6N2O3 |
M.W : | 190.16 |
SMILES Code : | OC1=CC([N+]([O-])=O)=C2N=CC=CC2=C1 |
MDL No. : | MFCD18448969 |
InChI Key : | AZDVQVFOHUFHOP-UHFFFAOYSA-N |
Pubchem ID : | 226259 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 52.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
78.94 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.9 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.85 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.1 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.45 |
Solubility | 0.672 mg/ml ; 0.00353 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.81 |
Solubility | 0.297 mg/ml ; 0.00156 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.51 |
Solubility | 0.589 mg/ml ; 0.0031 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) |
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 |
-6.37 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) |
1.88 |
* 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 |
---|---|---|
95% | Stage #1: for 16 h; Heating / reflux |
Example 35; N-(6-(benzyloxy)quinolin-8-yl)-6-(sulfamoylamino)hexanamide (43) Step 1: 8-nitroquinolin-6-ol (38) 6-methoxy-8-nitroquinoline (2.15 g, 10.51 mmol) was dissolved in 48percent HBr (8.0 mL, 147.20 mmol) and refluxed for 16 hours. The resulting suspension of yellow crystals was cooled down and then filtered. The solid was diluted in water and 15percent NaOH (aq) was added. The suspension was filtered and the aqueous layer was acidified to obtain crystals at pH6. Crystals were washed with water and filtered to afford compound 38 as yellow crystals (1.89 g, 95percent). LRMS (ESI): (calc.) 190.04 (found) 191.1 (MH)+. |
74% | With hydrogen bromide; acetic acid In water at 130℃; for 48 h; | 6-Methoxy-8-nitro-quinoline (2.0 g) was dissolved in a mixed solution of 48percent aq. HBr in HOAc (v/v 3:2) and then the reaction was refluxed at 130 °C for 2 days. The mixture was cooled to rt and filtered to provide a yellow solid, which was then dispensed in sat. NaHCO3 solution (aq.) for 1 h, filtered again and dried over Na2SO4 to afford the desired compound NY-1-31 (1.38 g, 74 percent) as a light yellow solid. 1H NMR 300 MHz, DMSO-c) δ 10.80 (s, 1H), 8.78 (dd, J = 4.2, 1.6 Hz, 1H), 8.35 (dd, J= 8.5, 1.6 Hz, 1H), 7.80 (d, J = 2.6 Hz, 1H), 7.59 (dd, J = 8.4, 4.2 Hz, 1H), 7.45 (d, J = 2.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With hydrogenchloride; phosphoric acid In water at 80℃; for 4 h; | 5.0 g of 4-amino-3-nitrophenol (compound a, 32 mmol), 40 mL of concentrated hydrochloric acid and 15 g of concentrated phosphoric acid were added to a reaction vessel and heated to 80 ° C., 6.5 mL (97 mmol) of acrolein was slowly added added. After reacting for 4 hours, the reaction solution was allowed to cool to room temperature, distilled water was added, and the mixture was filtered through Celite (Celite Corporation). The filtrate was neutralized with aqueous ammonia to give a red precipitate. The precipitate was collected by filtration and dried under vacuum to give a red solid (yield: 3.0 g, yield: 49percent). |