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CAS No. : | 312756-74-4 | MDL No. : | MFCD00348720 |
Formula : | C20H16Br2N2O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SWKAVEUTKGKHSR-UHFFFAOYSA-N |
M.W : | 524.23 | Pubchem ID : | 1039737 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.05 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 116.44 |
TPSA : | 83.65 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 2.74 |
Log Po/w (XLOGP3) : | 4.6 |
Log Po/w (WLOGP) : | 5.68 |
Log Po/w (MLOGP) : | 4.06 |
Log Po/w (SILICOS-IT) : | 3.96 |
Consensus Log Po/w : | 4.21 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.0 |
Solubility : | 0.000522 mg/ml ; 0.000000996 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.08 |
Solubility : | 0.000435 mg/ml ; 0.000000829 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.31 |
Solubility : | 0.000000256 mg/ml ; 0.0000000005 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.82 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
32% | Stage #1: With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.25 h; Reflux Stage #2: With triethylamine In tetrahydrofuran |
3-Benzylsulfamoyl-4-bromo-N-(4-bromo-phenyl)-benzamide ("RS-1"): 3- benzylsulfamoyl-4-bromo-benzoic acid (455 mg, 1.23 mmol) was dissolved in 5 mL of THF and 0.1 mL of DMF was added. To the reaction mixture oxalyl chloride (0.21 mL, 2.46 mmol) was added at room temperature. Reaction mixture was refluxed for 15 min, cooled and volatiles were removed under vacuum. Residue was re-dissolved in 5 mL of THF and 4- bromoaniline (254 mg, 1.48 mmol) in 1 mL of THF was added drop-wise followed by drop- wise addition of triethylamine (0.17 mL, 1.23 mmol). Reaction was stirred at room temperature for 2 h and 10 mL of ethyl acetate and 10 mL of water were added. Aqueous phase were further extracted with two portions of 15 mL of ethyl acetate. Organic phases were combined, washed with brine and dried with sodium sulfate. Solvents were evaporated and residue purified by preparative HPLC giving 257 mg (32percent) of 3-benzylsulfamoyl-4- bromo-N-(4-bromo-phenyl)-benzamide as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 10.60 (s, 1H), 8.55 (t, J = 6.1 Hz, 1H), 8.45 (d, J = 2.1 Hz, 1H), 8.01 (dd, J = 2.1 Hz, J = 6.3 Hz, 1H), 7.95 (d, J = 8.2 Hz, 1H), 7.75 (d, J = 7 Hz, 2H), 7.57 (d, J = 8.8 Hz, 2H), 7.22 (m, 5H), 4.15 (d, J= 6.2 Hz, 2H). 13C-NMR (100 MHz, DMSO-d6): δ 164.0, 140.7, 138.6, 137.8, 135.8, 134.5, 132.7, 132.0, 130.4, 128.5, 128.0, 127.6, 123.3, 122.9, 116.3, 46.5. |