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CAS No. : | 71203-35-5 | MDL No. : | MFCD05987165 |
Formula : | C22H21N3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QBNZBMVRFYREHK-UHFFFAOYSA-N |
M.W : | 407.49 | Pubchem ID : | 2950007 |
Synonyms : |
CID-2950007
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 119.75 |
TPSA : | 93.37 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 2.79 |
Log Po/w (XLOGP3) : | 3.56 |
Log Po/w (WLOGP) : | 3.69 |
Log Po/w (MLOGP) : | 2.51 |
Log Po/w (SILICOS-IT) : | 2.79 |
Consensus Log Po/w : | 3.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.74 |
Solubility : | 0.00744 mg/ml ; 0.0000183 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.21 |
Solubility : | 0.00253 mg/ml ; 0.00000622 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.01 |
Solubility : | 0.0000398 mg/ml ; 0.0000000977 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
37% | With acetic acid In ethanol at 150℃; for 1 h; Microwave irradiation; Sealed tube | 4-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]benzenesulfonamide For the synthesis of this compound, the requisite chalcone starting material was commercially available. 4-Methoxychalcone (3, R1=H, R2=4-OMe, CASNo.959-33-1) was purchased from Sigma-Aldrich and 4-hydrazinobenzene-1-sulfonamide hydrochloride (4, CASNo.17852-52-7) was purchased from Acros Organics. (STEP 2): To a 20 mL microwave vial was added 4-methoxychalcone (0.238 g, 1.00 mmol, 1 eq), EtOH (200 proof, 10 mL), 4-hydrazinobenzene-1-sulfonamide hydrochloride (0.252 g, 1.13 mmol, 1.1 eq), and glacial AcOH (0.29 mL, 5.0 mmol, 5 eq). The vessel was sealed and then submitted to microwave irradiation at 150° C. for 1 h. Once the reaction mixture had cooled to room temperature, the cap was removed and the vessel was placed in a dry-ice/acetone bath. While stirring, hexane (10 mL) was added, and the resulting precipitate was collected by filtration. The precipitate was rinsed with hexane (3*10 mL) and then the solid was transferred to another flask and recrystallized from EtOH (6 mL). The solid was filtered, rinsed with hexanes (3*10 mL) and dried to afford 4-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1Hpyrazol-1-yl)benzenesulfonamide (0.150 g, 37percent yield, 97percent purity) as white needles. 1H NMR (400 MHz, DMSO-d6) δ 7.80 (m, 2H), 7.58 (d, J=9.0 Hz, 2H), 7.43 (m, 3H), 7.18 (d, J=8.7 Hz, 2H), 7.09 (d, J=9.0 Hz, 2H), 7.02 (s, 2H), 6.90 (d, J=8.7 Hz, 2H), 5.60 (dd, J=12.0, 5.1 Hz, 1H), 3.95 (dd, J=17.6, 12.0 Hz, 1H), 3.71 (s, 3H), 3.17 (dd, J=17.7, 5.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) δ 158.59, 149.58, 145.87, 133.48, 132.98, 13 1.83, 129.24, 128.69 (*2), 127.06 (*2), 126.99 (*2), 126.02 (*2), 114.42 (*2), 112.02 (*2), 61.88, 55.02, 42.97. Compounds of this chemotype submitted to LCMS analysis routinely showed a parent mass and/or a parent mass-2, the latter of which resulted presumably due to an analytical instrument artifact that resulted in oxidation/aromatization of the central dihydropyrazoline ring on the LCMS column, in the MS detector, or both. In this case, both ions were observed in the same peak. LCMS retention time: 3.057 min. HRMS m/z calculated for C22H21N3NaO3S [M++Na]: 430.1196. found 430.1180. For aromatized/oxidized signal, HRMS m/z calculated for C22H20N3O3S [M+-2+1] 406.1225. found 406.1217. White needles, mp 185-187° C. (Faid-Allah, 1988). |