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CAS No. : | 1476-53-5 | MDL No. : | MFCD00066541 |
Formula : | C31H35N2NaO11 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 634.61 | Pubchem ID : | - |
Synonyms : |
Albamycin sodium;Cathomycin sodium;Novobiocin (sodium salt);NSC 2382
|
Num. heavy atoms : | 45 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.39 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 11.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 158.12 |
TPSA : | 202.84 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.81 cm/s |
Log Po/w (iLOGP) : | -9.93 |
Log Po/w (XLOGP3) : | 3.32 |
Log Po/w (WLOGP) : | 3.87 |
Log Po/w (MLOGP) : | 0.91 |
Log Po/w (SILICOS-IT) : | 2.85 |
Consensus Log Po/w : | 0.21 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -5.47 |
Solubility : | 0.00215 mg/ml ; 0.00000339 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.26 |
Solubility : | 0.0000352 mg/ml ; 0.0000000555 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.91 |
Solubility : | 0.000781 mg/ml ; 0.00000123 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 6.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
42% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Novobiocin sodium salt (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated novobiocin ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%), mp 115-125 C. 1H NMR (400 MHz, MeOD): delta 1.23-1.29 (15H, m, H-6, COCH(CH3)2), 1.42 (3H, s, H-7), 2.33 (3H, s, H-10'), 2.70 (1H, h, J 7.0 Hz, COCH(CH3)2), 2.88 (1H, h, J 6.8 Hz, COCH(CH3)2), 3.52 (1H, d, J 8.9 Hz, H-4), 3.60 (3H, s, H-8), 5.45-5.48 (2H, m, H-2, H-3), 5.64 (1H, d, J 2.4 Hz, H-1), 7.22 (1H, d, J 8.9 Hz, H-5'), 7.79 (1H, d, J 8.8 Hz, H-4'). 13C NMR (125.7 MHz, MeOD) delta 9.5, 20.0, 20.3, 20.7 (2C), 24.3, 29.6, 36.1, 37.0, 62.7, 71.6, 72.5, 80.8, 83.9, 98.0, 104.4, 112.5, 113.4, 115.8, 124.1, 152.5, 158.7, 159.4, 159.5, 163.7, 178.3, 181.8. Positive HRESIMS, m/z calcd 587.2217 for C27H36N2O11Na, found 587.2222 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: <strong>[1476-53-5]Novobiocin sodium salt</strong> (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated <strong>[1476-53-5]novobiocin</strong> ([M-H]-, m/z 752.0). After heating the reaction to 70 C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95% A for 4 min followed by 95-0% A over 20 min and 100% B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Novobiocin sodium salt (200 mg, 0.31 mmol) was dissolved in DMF (3 mL). Isobutyric anhydride (0.41 mL, 2.52 mmol) and pyridine (0.2 mL, 2.52 mmol) were added, and the solution was stirred at ambient temperature. Monitoring of the reaction by ESI-MS indicated the disappearance of the starting material ([M-H]-, m/z 611.7) and the formation of the di-acylated novobiocin ([M-H]-, m/z 752.0). After heating the reaction to 70 °C for an additional 8 h, full conversion to enamide 10 ([M-H]-, m/z 563.8) was detected. Upon complete conversion, the crude was evaporated under vacuum, re-dissolved in a minimal volume of CH3CN and purified by reverse-phase HPLC at a flow rate of 15.0 mL/min. HPLC solvent A was H2O and solvent B was CH3CN. The elution gradient was 95percent A for 4 min followed by 95-0percent A over 20 min and 100percent B for 3 min. The product was detected at 210 and 254 nm using a double-channel UV detector (product retention time=25.5 min). Fractions containing the pure product were concentrated under vacuum, dissolved in H2O and freeze dried to yield enamide 10 as a white solid (142 mg, 80percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.3% | With hydrogenchloride; In water; | A solution of NB monosodium salt (1b, 30g) in water (400mL) was acidified with 2M aq. HCl (pH ?2; just until no further precipitation occurs) and extracted with EtOAc (3×400mL). The EtOAc layer was dried (Na2SO4) and evaporated to dryness to afford 1a (28.7g; 99.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.6% | With sodium cyanide; In methanol;Reflux; | General procedure: 4.2.6 General procedure for deacylation: To a stirred solution/suspension of the starting material in MeOH (2 mL) was added NaCN (1:4) and continued stirring until the reaction is complete (monitored by TLC) at 25 C unless otherwise stated. Reaction mixture was diluted with brine, acidified with 2M aq. HCl and extracted into EtOAc. EtOAc layer was washed with brine and dried (Na2SO4) and solvent were removed to obtain the crude product. Novobiocin monosodium salt (1b, 500.0 mg, 0.79 mmol) was subjected to general procedure of deacylation under reflux and the crude product on flash chromatography (eluent: 3% MeOH in CH2Cl2) afforded 12 as a white solid (357.0 mg; 79.6 %): mp 168-170C. 1H NMR data were consistent with those reported.24 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 20℃; for 72.0h;Molecular sieve; Inert atmosphere; | General procedure: A mixture of <strong>[1476-53-5]<strong>[1476-53-5]novobiocin</strong> sodium</strong> (200 mg, 0.32 mmol), 1-Bromine-2,3,4,6-tetra-O-acetyl-a-D-glucose/galactose (0.132g,0.32 mmol), activated 4 A molecular sieves (approx. 1.5g) and anhydrous DMF (anhydrous, 20 ml, or other solvent as in Table 1)were added into a 250 ml flask. Catalyst (eqv. shown in Table 1) was added into the reaction. The reaction mixture was stirred for 3 days under nitrogen gas protection at room temperature covered by foil and monitored by LC/MS. Water (120 ml) was added into the system and the crude product was extracted by chloroform. The crude product was purified by flash column (ethyl acetate/petroleumether/methanol 12/4/1, Rf 0.3) to afford a white powder (yield;see Table 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 20℃; for 72.0h;Molecular sieve; Inert atmosphere; | General procedure: A mixture of <strong>[1476-53-5]<strong>[1476-53-5]novobiocin</strong> sodium</strong> (200 mg, 0.32 mmol), 1-Bromine-2,3,4,6-tetra-O-acetyl-a-D-glucose/galactose (0.132g,0.32 mmol), activated 4 A molecular sieves (approx. 1.5g) and anhydrous DMF (anhydrous, 20 ml, or other solvent as in Table 1)were added into a 250 ml flask. Catalyst (eqv. shown in Table 1) was added into the reaction. The reaction mixture was stirred for 3 days under nitrogen gas protection at room temperature covered by foil and monitored by LC/MS. Water (120 ml) was added into the system and the crude product was extracted by chloroform. The crude product was purified by flash column (ethyl acetate/petroleumether/methanol 12/4/1, Rf 0.3) to afford a white powder (yield;see Table 1). |