Structure of 563-63-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 563-63-3 |
Formula : | C2H3AgO2 |
M.W : | 166.91 |
SMILES Code : | CC([O-])=O.[Ag+] |
MDL No. : | MFCD00012446 |
InChI Key : | CQLFBEKRDQMJLZ-UHFFFAOYSA-M |
Pubchem ID : | 11246 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H319-H372-H410 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 5 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 11.56 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.13 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.21 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.24 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.49 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.74 |
Solubility | 30.2 mg/ml ; 0.181 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.18 |
Solubility | 111.0 mg/ml ; 0.667 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.53 |
Solubility | 571.0 mg/ml ; 3.42 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.47 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
38% | With acetic acid; palladium dichloride; for 24h;Reflux; | General procedure: Iodo methyl benzoate (0.5 g, 1.90 mmol), silver acetate (0.47 g, 2.85 mmol), sodium acetate (0.77g,9.50 mmol) and PdCl2 (34 mg, 0.19 mmol) were dissolved in AcOH (5 mL). Reaction mixture wasrefluxed for 24 h. The mixture was poured in the saturated NH4Cl and extracted with AcOEt. Theorganic phase was washed with water, dried over Na2SO4, filtered and concentrated under reducedpressure. The crude residue was purified with flash chromatography on silica gel, eluting with 50%AcOEt/Hex to give pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25%; 25% | With dimethyl sulfoxide; p-benzoquinone; palladium dichloride; In N,N-dimethyl-formamide; at 80℃; for 16h; | The compound 7 was obtained by the reaction of 1j with the pinacol methylboronate, benzylboronate or allylboronate under the standard conditions (Scheme 4b). Yellow oil. 1H NMR (400MHz, CDCl3) delta 7.90?7.76 (m, 4H), 7.60 (d, J=8.6Hz, 1H), 7.54?7.39 (m, 2H), 5.71 (s, 1H), 5.48 (s, 1H), 5.11 (s, 2H), 2.09 (s, 3H). 13C NMR (101MHz, CDCl3) delta 171.0, 142.5, 135.4, 133.4, 133.2, 128.4, 128.3, 127.7, 126.5, 126.4, 125.0, 124.3, 115.9, 65.9, 21.2, 21.1. IR (neat, cm-1) 475.93 (m), 750.80 (s), 817.87 (m), 905.90 (m), 1027.91 (m), 1227.18 (s), 1369.63 (s), 1740.40 (s), 3055.22 (w). HRMS (APCI) Calcd for C15H15O2+ [M+H]+ 227.1067; Found 227.1069. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100℃; for 16h;Schlenk technique; | In the dried Schrank tube, raw porphyrin (0.15 mmol, 26.2 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg), iodobenzene acetate were added in sequence.(0.15 mmol, 48.3 mg), pentamethylcyclopentadienylphosphonium dichloride (5 mmol%, 4.6 mg), silver triflate (20 mmol%, 7.7 mg),Silver acetate (20 mmol%, 5.1 mg), acetic acid (0.45 mmol, 27 mg)1.5 mL of 1,2-dichloroethane, and the above-mentioned Schalke tube was placed in a 100 o C oil bath.Stir for about 16 h. Stop the reaction,The reaction solution is easily quenched using 2 mL of saturated ammonium chloride.After further extraction with ethyl acetate (4 mL × 5), the organic phases were combined.The solvent was removed on a rotary evaporator. Finally, separation by silica gel column chromatography(eluent: ethyl acetate: petroleum ether = 1: 5),Obtaining N-(1-acetyl-5-methylporphyrin-7-yl)-4-methylbenzenesulfonamide 3e(46.4 mg, isolated yield: 90%).This compound was a pale yellow solid. |