Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 431980-38-0 | MDL No. : | MFCD03142961 |
Formula : | C20H16N2O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JKNUDHUHXMELIJ-UHFFFAOYSA-N |
M.W : | 380.42 | Pubchem ID : | 1317590 |
Synonyms : |
|
Chemical Name : | N-(2-Methoxyphenyl)-2-((4-nitrophenyl)thio)benzamide |
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.05 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 106.54 |
TPSA : | 109.45 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) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 4.63 |
Log Po/w (WLOGP) : | 4.82 |
Log Po/w (MLOGP) : | 3.41 |
Log Po/w (SILICOS-IT) : | 2.15 |
Consensus Log Po/w : | 3.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.15 |
Solubility : | 0.00271 mg/ml ; 0.00000713 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.65 |
Solubility : | 0.0000843 mg/ml ; 0.000000222 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -6.99 |
Solubility : | 0.0000391 mg/ml ; 0.000000103 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.64 |
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 |
---|---|---|
63% | With potassium carbonate; ethylene glycol In isopropyl alcohol at 20℃; for 1 h; microwave irradiation | Method A: Synthesis of 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) Vif inhibitor 1 was synthesized using the procedure outlined in Scheme 9. The key step in this reaction scheme is the copper catalyzed coupling reaction of 2-iodo-N-(2-methoxyphenyl)benzamide 3 with 4-nitrothiophenol 4 by microwave irradiation. The intermediate compound 3 was obtained in excellent yield by the reaction of 2-methoxyaniline 5 with 2-iodobezoyl chloride 2. Scheme 9: (a) Et3N, CH2Cl2, 0° C. to r. t. overnight, 98percent; (b) K2CO3, Cu(I)I (cat.), HOCH2CH2OH, 2-propanol, microwave-150 W, 80° C., 30 min (2.x.), 63percent. 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) 2-Iodo-N-(2-methoxyphenyl)benzamide 3 (0.355 g, 1.0 mmol), Cu(I) iodide (20 mg, 0.1 mmol), K2CO3 (0.276 g, 2.0 mmol), and 4-nitrothiophenol (0.155 g, 1 mmol) were added to a 10 mL reaction vessel with Teflon-lined septum. The tube was evacuated and backfilled with dry N2 (3 cycles). Ethylene glycol (0.1 mL, 2.0 mmol) and 2-propanol (1 mL) were added by syringe at room temperature. The reaction vessel was heated in a microwave reactor (CEM, Explorer) at 80° C. and 150 W power for 30 min (2.x.). The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 10 mL) was added; the reaction mixture was filtered and concentrated. The crude product was purified by flash column chromatography on silica, eluting with 20percent EtOAc in hexanes. This procedure provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1 as pale yellow crystalline solid (0.24 g, 63percent); 1H NMR (400 MHz, CDCl3) δ 8.40 (d, J=8.0 Hz, 1H), 8.39 (s, 1H, overlapping signal), 8.05 (ddd, J=9.2, 2.4, 1.6 Hz, 2H), 7.77 (dd, J=6.4, 2.4 Hz, 1H), 7.56-7.49 (m, 3H), 7.29-7.25 (m, 2H), 7.06 (ddd, J=9.2, 7.6, 1.6 Hz, 1H), 6.95 (dt, J=8.8, 0.8, 1.2 Hz, 1H), 6.85 (dd, J=8.0, 0.8 Hz, 1H), 3.78 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 165.44, 148.22, 146.87, 146.15, 140.63, 135.76, 131.66, 130.09, 129.87, 129.49, 128.79 (2C), 127.54, 124.54, 124.35 (2C), 121.37, 120.05, 110.19, 55.88; MS (ESI): m/z 402.99 (M+Na)+. |