Structure of 25477-96-7
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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. : | 25477-96-7 |
Formula : | C9H11N5O2 |
M.W : | 221.22 |
SMILES Code : | NC1=NC=NC2=C1N=CN2CC(OCC)=O |
MDL No. : | MFCD01321238 |
InChI Key : | MCOVDURKZQNFBE-UHFFFAOYSA-N |
Pubchem ID : | 688302 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 56.7 |
TPSA ? Topological Polar Surface Area: Calculated from |
95.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.55 |
Solubility | 6.19 mg/ml ; 0.028 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.88 |
Solubility | 2.94 mg/ml ; 0.0133 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.88 |
Solubility | 2.94 mg/ml ; 0.0133 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 |
-7.44 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) |
2.3 |
* 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 |
---|---|---|
59% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; Inert atmosphere Stage #2: for 2 h; Inert atmosphere |
General procedure: To a suspension of 9H-purine (1c, 1.20 g, 10.0 mmol) in anhydrous DMF (15 mL) at 0 °C was added sodium hydride (0.48 g, 12.0 mmol) in batches and then stirred vigorously 1 hour at room temperature under argon. Ethyl bromoacetate (1.33 mL, 12.0 mmol) was added dropwise via syringe and stirred continuously for another 2 hours. The solvent was evaporated in vacuo pressure. Water (15 mL) was added to the residue and extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over Na2SO4, and evaporated, in vacuo. The residue was purified by chromatography on a silica gel column (30 × 6 cm). Elution with 1:2 to 1:3 hexanes- ethyl acetate gave 3a as white powder. |
20% | With potassium carbonate In water; N,N-dimethyl-formamide | EXAMPLE 26 Synthesis of 9-carboxymethyladenine ethyl ester Adenine (10 g, 74 mmol) and potassium carbonate (10.29 g, 74 mmol) were suspended in DMF and ethyl bromoacetate (8.24 mL, 74 mmol) was added. The suspension was stirred for 2.5 h under nitrogen at room temperature and then filtered. The solid residue was washed three times with DMF (10 mL). The combined filtrate was evaporated to dryness, in vacuo. Water (200 mL) was added to the yellowish-orange solid material and the pH adjusted to 6 with 4 N HCl. After stirring at 0° C. for 10 minutes, the solid was filtered off, washed with water, and recrystallized from 96percent ethanol (150 mL). The title compound was isolated by filtration and washed thoroughly with ether. Yield: 3.4 g (20percent). M.p. 215.5-220° C. Anal. for C9H11N5O2 found(calc.): C: 48.86(48.65); H: 5.01(4.91); N: 31.66(31.42). 1H-NMR (250 MHz; DMSO-d6): 7.25 (bs, 2H, NH), 5.06 (s, 2H, NCH2), 4.17 (q, 2H, J=7.11 Hz, OCH2) and 1.21 (t, 3H, J=7.13 Hz, NCH2). 13C-NMR. 152.70, 141.30, 61.41, 43.97 and 14.07. FAB-MS. 222 (MH+). IR: Frequency in cm-1 (intensity). 3855 (54.3), 3274(10.4), 3246(14.0), 3117(5.3), 2989(22.3), 2940(33.9), 2876(43.4), 2753(49.0), 2346(56.1), 2106(57.1), 1899(55.7), 1762(14.2), 1742(14.2), 1742(1.0), 1671(1.8), 1644(10.9), 1606(0.6), 1582(7.1), 1522(43.8), 1477(7.2), 1445(35.8) and 1422(8.6). |
20% | With potassium carbonate In water; N,N-dimethyl-formamide | EXAMPLE 26 Synthesis of 9-carboxymethyladenine ethyl ester Adenine (10 g, 74 mmol) and potassium carbonate (10.29 g, 74 mmol) were suspended in DMF and ethyl bromoacetate (8.24 mL, 74 mmol) was added. The suspension was stirred for 2.5 h under nitrogen at room temperature and then filtered. The solid residue was washed three times with DMF (10 mL). The combined filtrate was evaporated to dryness, in vacuo. Water (200 mL) was added to the yellowish-orange solid material and the pH adjusted to 6 with 4N HCl. After stirring at 0° C. for 10 minutes, the solid was filtered off, washed with water, and recrystallized from 96percent ethanol (150 mL). The title compound was isolated by filtration and washed thoroughly with ether. Yield: 3.4 g (20percent). M.p. 215.5°-220° C. Anal. for C9 H11 N5 O2 found(calc.): C: 48.86(48.65); H: 5.01(4.91); N: 31.66(31.42). 1 H-NMR (250 MHz; DMSO-d6): 7.25 (bs, 2H, NH2), 5.06 (s, 2H, NCH2), 4.17 (q, 2H, J=7.11 Hz, OCH2) and 1.21 (t, 3H, J=7.13 Hz, NCH2). 13 C-NMR. 152.70, 141.30, 61.41, 43.97 and 14.07. FAB-MS. 222 (MH+). IR: Frequency in cm-1: 3855, 3274, 3246, 3117, 2989, 2940, 2876, 2753, 2346, 2106, 1899, 1762, 1742, 1742, 1671, 1644, 1606, 1582, 1522, 1477, 1445 and 1422. |
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