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CAS No. : | 956590-23-1 | MDL No. : | MFCD22380608 |
Formula : | C17H18N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCKZRLOUKYFJDY-UHFFFAOYSA-N |
M.W : | 326.35 | Pubchem ID : | 16048966 |
Synonyms : |
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 13 |
Fraction Csp3 : | 0.24 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 94.35 |
TPSA : | 97.43 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.73 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 0.79 |
Log Po/w (WLOGP) : | 0.81 |
Log Po/w (MLOGP) : | 1.49 |
Log Po/w (SILICOS-IT) : | 1.08 |
Consensus Log Po/w : | 1.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.43 |
Solubility : | 1.21 mg/ml ; 0.0037 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 1.25 mg/ml ; 0.00383 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.48 |
Solubility : | 0.0108 mg/ml ; 0.0000332 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
76% | With sodium hydroxide; water for 1h; Heating / reflux; | 2 Example 2 - preparation of /v-{2-r2-(dimethylamino)ethyl1-1 ,3-dioxo-2,3-dihydro-1H- benzo[cfelisoquinolin-5-yl)urea; 100 mg of the compound of example 1 were dissolved in 100 mL of NaOH 0.1 M. The reaction mixture was warmed up to reflux and maintained at this temperature during 1 hour. The mixture was analysed by HPLC, showing the presence of the expected urea (structural formula below) as the major product (yield 76 %).This product was characterised by the following techniques: - proton nuclear magnetic resonance (RMN 1H, 300 MHz, DMSO) showing peaks at: 9.40 (NH-17, bs) ; 8.53 (H-2, d, J = 1.8); 8.48 (H-4, d, J = 1.8); 8.26-8.32 (H-6 and H-7, m); 6.18 (NH2-19, bs) ; 4.14 (H-14, t, J = 6.6); 2.51 (H-13, m); and 2.21 (H-15 and H-16, s) ppm;- 13C NMR (75.4 MHz, DMSO, TMS as internal standard) showing peaks at 37.5 (CH2, C-13); 49.9 (2 X CH3, C-15 and C-16) ; 57.0 (CH, C14); 1 19.0(CH, C-arom); 122.2 (C, C-arom); 122.9 (C, C-arom); 123.5 (C, C-arom);123.9 (CH, C-arom); 127.8 (CH, C-arom); 128.6 (CH, C-arom); 132.7 (C, C- arom); 133.8 (CH, C-arom); 140.3 (C, C-arom); 156.5 (C, C-18); and 163.8(C, C-12); 164.0 (C, C-1 1 ) ppm; and - electron-spray ionisation mass spectrum: showing a peak at M+H+= 327 and an adduct at 2M + H+ = 653. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With methanol; water; potassium carbonate at 8 - 56℃; for 7.5 - 7.75h; | 7 Example 7 - alternative preparation of λ/-{2-[2-(dimethylamino)ethyl1-1 ,3-dioxo-2,3- dihydro-1H-benzo[c/elisoquinolin-5-yl)urea; A 3-necked 22-L round bottomed flask equipped with mechanical stirrer, reflux condenser, and temperature controller was charged with the compound of example 6 (250 g) and 7.5 L of a 5% solution of K2CO3 in water. The mixture was cooled to 10 0C with (ice bath), and then 7.5 L of methanol (MeOH) was added in one portion. The temperature rose to 20 0C. The flask was removed from the ice bath and stirring was continued at ambient temperature until most of the starting material dissolved (about 30-45 min). The mixture was quickly filtered (clarified), to remove the small amounts of unreacted materials and other mechanical impurities. The mixture was stirred at room temperature for 2 hours, and 4 L of MeOH was charged in one portion. The mixture was heated at 54-56 0C for 3 hours. Reaction progress was monitored by HPLC to ensure completion. The reaction mixture was cooled (ice bath) and kept at 8-10 0C for 2 hours. The obtained solid was isolated by filtration, washed on the filter (2 x 100 mL of water), and then dried in air for 2 days to give 156 g (yield: 90%) of the desired compound (HPLC purity : 99.47%). The characterizing spectra of this compound were the same as described in example 2 herein-above. |