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CAS No. : | 4727-31-5 | MDL No. : | MFCD00560510 |
Formula : | C20H15NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SLUINPGXGFUMLL-UHFFFAOYSA-N |
M.W : | 317.34 | Pubchem ID : | 2826191 |
Synonyms : |
KGN
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 93.05 |
TPSA : | 66.4 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.23 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 4.23 |
Log Po/w (WLOGP) : | 4.11 |
Log Po/w (MLOGP) : | 3.77 |
Log Po/w (SILICOS-IT) : | 3.62 |
Consensus Log Po/w : | 3.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.7 |
Solubility : | 0.00637 mg/ml ; 0.0000201 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.34 |
Solubility : | 0.00147 mg/ml ; 0.00000462 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.79 |
Solubility : | 0.0000519 mg/ml ; 0.000000164 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
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 |
---|---|---|
benzylidene derivatives: for example ... 3-(2,4,6-TRIMETHYLBENZOYL)-2-BIPHENYLCARBOXYLIC ACID, 2'-BENZYLCARBAMOYLBIPHENYL-2-CARBOXYLIC ACID, 3-CHLORO-3'-METHYLBIPHENYL-2,2'-DICARBOXYLIC ACID, 2-HO-5-(4'-HO-BIPHENYL-4-YLAZO)BENZOIC ACID, 2-[([1,1'-BIPHENYL]-4-YLAMINO)CARBONYL]BENZOIC ACID, 3-(1-[1,1'-BIPHENYL]-4-YL-1H-1,2,3,4-TETRAAZOL-5-YL)QUINOLIN-4(1H)-ONE, 2-[[(3-[1,1'-BIPHENYL]-4-YL-3-OXOPROPYLIDENE)AMINO]OXY]-N-(5-IODO-2-PYRIDINYL)ACETIC ACID, 4,4'-DI-BOC-DIAMINOBIPHENYL-2,2'-DICARBOXYLIC ACID, 2,3,2'-BIPHENYLTRICARBOXYLIC ACID, ... | ||
With dmap; In tetrahydrofuran; chloroform; at 20℃; | General procedure: To a solution of phthalic anhydride (1.05 equiv) in a 3:1mixture of chioroformlTHF (0.05 M concentration) wasadded the corresponding amine (RArNH2, 1 equiv). Themixture was stirred overnight at room temperature. Thereaction mixture was washed with brine (x2). The aqueoussolution was then extracted with ethyl acetate (x3) and driedover sodium sulfate. Combined organic phases were concentrated under reduced pressure and adsorbed on silica gelto be purified by flash chromatography to afford the desiredamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of acid and diisopropylethylamine (DIEA, 2.2 equiv) in DMF (0.1 M concentration) at 00 C. was added the corresponding amine 1.2 equiv). The mixture was stirred for 30 mm and PyBOP (1.1 equiv) was added and stirred at room temperature for 6 h. The slurry reactionmixture was washed with brine (x5 to assure complete removal of DMSO; volume of brine .-10 times volume of DMSO). The aqueous solution was then extracted with ethyl acetate (x3) and dried over sodium sulfate. Combined organic phases were concentrated under reduced pressureand adsorbed on silica gel to be purified by flash chromatography to afford the desired amide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; dimethyl sulfoxide; at 0 - 20℃; for 12.5h; | General procedure: DCC (0.9equiv) and DMAP (0.2 equiv) were added to a solution of the selected alcohol (1.2 equiv) in CH2C12/DMSO (2:1; 0.1 M) at 0 C. The mixture was stirred for 30 mm before acid (1 equiv) was introduced and stirring continued for 12 h at ambient temperature. For work up, all volatile materials were evaporated, the product adsorbed on silica and purified by flash chromatography (hexanes/ethyl acetate) to give the desired product (yield .-75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; water; dimethyl sulfoxide; at 0 - 20℃; for 74h; | Before the PEGylation was carried out on a <strong>[4727-31-5]kartogenin</strong> derivative, a relatively unstable ester bond was produced in <strong>[4727-31-5]kartogenin</strong> (<strong>[4727-31-5]KGN</strong>, MW=317.34 Da, Tocris Bioscience, Bristol, UK) by using 3-hydroxypropanoic acid. (0095) Specifically, <strong>[4727-31-5]KGN</strong> (31.7 mg, 0.1 mmol in dimethyl sulfoxide (DMSO)) was dissolved in 10 mL of anhydrous CH2Cl2, the resulting solution was cooled to 0 C., and then 3-hydroxypropanoic acid (Toronto Research Chemicals, TRC, Toronto, Canada, a 30% aqueous solution, 30.2 muL, 0.1 mmol), dicyclohexylcarbodiimide (DCC, Sigma-Aldrich, St Louis, Mo., USA, 30 mg, 0.15 mmol), and 4-dimethylaminopyridine (DMAP, Sigma-Aldrich, St Louis, Mo., USA, 15 mg, 0.15 mmol) were added thereto. After the solution was stirred at 0 C. for 2 hours, stirred at room temperature (RT) for 72 hours, and filtered, the resulting material was precipitated three times with anhydrous diethyl ether, and then carboxylated <strong>[4727-31-5]KGN</strong> (COOH-<strong>[4727-31-5]KGN</strong>; a white powder) was obtained by drying the precipitate under vacuum. |