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CAS No. : | 1020149-73-8 | MDL No. : | MFCD27937047 |
Formula : | C27H23N7O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QSYLKMKIVWJAAK-UHFFFAOYSA-N |
M.W : | 461.52 | Pubchem ID : | 24858111 |
Synonyms : |
DNA Methyltransferase Inhibitor II
|
Num. heavy atoms : | 35 |
Num. arom. heavy atoms : | 28 |
Fraction Csp3 : | 0.04 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 140.0 |
TPSA : | 117.85 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.72 cm/s |
Log Po/w (iLOGP) : | 2.9 |
Log Po/w (XLOGP3) : | 4.78 |
Log Po/w (WLOGP) : | 5.47 |
Log Po/w (MLOGP) : | 2.8 |
Log Po/w (SILICOS-IT) : | 3.29 |
Consensus Log Po/w : | 3.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.84 |
Solubility : | 0.000663 mg/ml ; 0.00000144 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.99 |
Solubility : | 0.0000476 mg/ml ; 0.000000103 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -10.5 |
Solubility : | 0.0000000145 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 65℃; for 24 h; Inert atmosphere | To a solution of 4-(quinolin-4’-ylamino)benzoic acid 17 (45 mg, 0.17 mmol) and N4-(4’-aminophenyl)-2,4-diamino-6-methylpyrimidine 9 (37 mg, 0.17 mmol) in DMF (1.7 mL) was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.06 g, 0.34 mmol) and 1-hydroxybenzotriazole hydrate (0.03 g, 0.17 mmol) and the reaction was stirred for 24 h at 65 ºC. When the reaction was complete the solvent was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 85:13:2 CH2Cl2/MeOH/Et3N) to afford 0.05 g (59percent) of the titled compound as an amorphous yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.045 g | With palladium diacetate; potassium carbonate; XPhos In water; N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 110℃; for 24 h; Sealed tube; Inert atmosphere | A sealed tube was charged with Pd(OAc)2 (1 mg, 1.32 mmol) and XPhos (2 mg, 3.97 mmol) and degassed t-BuOH/water (1 mL, 2:1 v/v) was added. The resulting solution was heated for 1 min at 80 ºC and then cannulated into another sealed tube charged with 4-amino-N-[4-(2-amino-6-methylpyrimidine-4-ylamino)phenyl]benzamide 12 (0.07g, 0.20 mmol), 4-chloroquinoline 13 (22.0 mg, 0.13 mmol) and potassium carbonate (0.03 g, 0.18 mmol) in DMF (1 mL). The resulting mixture was stirred for 24 h at 110 ºC. When the reaction was complete the solvent was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 85:13:2 CH2Cl2/MeOH/Et3N) to afford 0.045 g (73percent by 1H-NMR) of the titled compound as an amorphous yellow solid. 1H-NMR (400.13 MHz, DMSO-d6): d 10.22 (s, 1H, CONH), 9.98 (s, 1H, NH), 8.59 (d, J = 5.6 Hz, 1H), 8.48 (d, J = 8.4 Hz, 1H), 8.05 (d, J = 8.7 Hz, 2H), 8.00-7.94 (m, 2H), 7.86 – 7.75 (m, 3H), 7.74 – 7.61 (m, 4H), 7.57 – 7.50 (m, 3H), 7.44 – 7.37 (m, 1H), 7.15 (d, J = 5.6 Hz, 1H), 6.04 (s, 1H, H5’’), 2.22 (s, 3H, CH3) ppm. 13C-NMR (100.62 MHz, DMSO-d6): d 164.7 (s, CONH), 161.4 (s), 157.1 (s), 154.9 (s), 149.5 (s), 147.8 (d), 145.0 (s), 142.9 (s), 135.4 (s), 134.2 (s), 131.3 (d), 130.2 (s), 129.3 (d, 2x), 125.9 (d, 2x), 123.0 (d, 2x), 121.7 (d), 121.6 (d, 2x), 120.8 (d, 2x), 119.4 (s), 102.5 (d), 96.4 (d), 19.4 (q, CH3) ppm. HRMS (ESI+): Calcd for C27H24N7O ([M + H]+), 462.20368; found, 462.20330. IR (neat): n 3400-3000 (br, N-H), 2976 (w, C-H), 2891 (w, C-H), 1584 (m), 1510 (m), 1444 (m), 1380 (m), 1318 (m), 1228 (w), 1180 (w), 1095 (w) cm-1. UV (DMSO): lmax 258, 355 nm. |