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CAS No. : | 1219810-16-8 | MDL No. : | MFCD30187526 |
Formula : | C23H21ClN2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TXJZRSRTYPUYRW-NQIIRXRSSA-N |
M.W : | 440.88 | Pubchem ID : | 1750826 |
Synonyms : |
(1S,3R)-RSL3
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.26 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 119.01 |
TPSA : | 88.7 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.48 cm/s |
Log Po/w (iLOGP) : | 3.01 |
Log Po/w (XLOGP3) : | 3.54 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.35 |
Log Po/w (SILICOS-IT) : | 3.95 |
Consensus Log Po/w : | 3.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.7 |
Solubility : | 0.0088 mg/ml ; 0.00002 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.09 |
Solubility : | 0.00361 mg/ml ; 0.00000818 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.51 |
Solubility : | 0.000136 mg/ml ; 0.000000308 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.89 |
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 |
---|---|---|
60% | With sodium hydrogencarbonate In chloroform at 0 - 20℃; for 4h; | 3 Synthesis of cis-, fraϖs-(3S)- and (3R)-methyl-1-(1 ,3-benzodioxol-5yl)-2- (chloroacetyl)-2,3,4,9-tetrahydro-1H-^-carboline-3-carboxilatesCompound 27[0351] Chloroacetyl chloride (0.096 mol) was slowly added to a cooled-on-ice, stirred solution of 4a or 4b (0.04 mol) and NaHCθ3 (0.048 mol) in dry chloroform (200 ml_). The reaction mixture was allowed to warm to room temperature and stirred for four hours. Dichloromethane (200 ml_) was added to the reaction mixture. The resulting solution was washed with NaHCθ3, washed with a saturated solution of NaCI, dried with MgSO4, and concentrated. The solid residue was triturated with ether, filtered off, and washed with small amount of methanol to yield the product. [0352] Cis-, trans- (3R)-methyl-1-(1 ,3-benzodioxol-5yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1 H-yβ-carboline-3-carboxilate: yield 60 %, M.p. 273-275°C. NMR1H {δ, ppm, DMSO-d6, 500 MHz): 2.86 (3H, s, OCH3); 3.11-3.50 (2H, m, CH2CI); 3.83 (3H, s, OCH3); 4.38 (1 H, d, ArCH2, JHH = 14 Hz); 4.77 (1 H, d, ArCH2, JHH = 14 Hz); 5.19 (1 H, d, ArCH, JHH = 2.5 Hz); 6.91 (1 H, s, Ar); 7.01-7.08 (2H, dt, Ar, JHH = 25 Hz, 3 Hz); 7.23-7.53 (3H, m, Ar); 7.85 (2H, d, Ar, JHH = 4 Hz); 10.82 (1 H, s, NH). NMR13C (δ, ppm, DMSO-d6, 125.76 MHz): 21.01(s), 42.78(s), 51.09(s), 51.39(s), 51.99(s), 52.48(S), 106.34(s), 111.10 (s), 118.02(s), 118.67 (s), 121.56(s), 125.79(s), 128.72(d), 128.90(s), 136.36(s), 144.50(s), 165.82(s), I66.87(s), 169.97(s). "V2 440(M+).[0353] Cis-, trans- (3S)-methyl-1-(1 ,3-benzodioxol-5yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1 H-0-carboline-3-carboxilate: yield 45 %, M.p. 272-273°C. NMR1H (<5, ppm, DMSO-d6, 500 MHz): 2.84 (1 H, s, OCH3); 3.12-3.49 (2H, m, CH2CI); 3.82 (3H, s, OCH3); 4.48 (1 H, d, ArCH2, JHH = 14Hz); 4.86 (1 H, d, ArCH2, JHH = 14 Hz); 5.23 (1 H, d, ArCH, JHH = 2.5 Hz); 6.91 (1 H1 s, Ar); 7.03-7.10 (2H, dt, Ar, JHH = 25 Hz, 3 Hz); 7.21-7.54 (3H1 m, Ar); 7.84 (2H, d, Ar, JHH = 4 Hz); 10.92 (1 H, s, NH). NMR13C (δ, ppm, DMSO-d6, 125.76 MHz): 21.07(s), 43.08(s), 51.15 (s), 51.50 (s), 52.13(s), 52.53 (s), 106.50(s), 111.25 (s), 118.10(s), 118.69 (s), 121.62(s), 125.87(s), 128.77(d), 128.95 (s), 136.43 (s), 144.69 (s), 165.92(s), 166.97(s), 170.09(s). m/z 440(M+). |
With sodium hydrogencarbonate In chloroform at 0 - 20℃; for 4h; | [0894] To a solution of AA-3 (4.50 g, 12.35 mmol, 1.00 eq) and NaHCO3 (1.25 g, 14.82 mmol, 576.40 μL, 1.20 eq) in CHCl3 (50.00 mL) was added slowly 2-chloroacetyl chloride (3.35 g, 29.64 mmol, 2.36 mL, 2.40 eq) at 0°C. The mixture was stirred at 20°C. for 4 h to give a black mixture. The completion of reaction was detected by TLC. The reaction mixture was diluted with DCM (20 mL), washed with a saturated solution of NaHCO3 and brine (10 mL each) in sequence. The organic layer was dried over Na2SO4, concentrated under reduced pressure. The product was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=10/1 to 4:1) to give K601 . LC-MS (m/z): 441.1 [M+H]+. 1H NMR (400 MHz, DMSO, T=80°C.) δ 10.80 (s, 1H), 7.88-7.86 (m, 2H), 7.60-7.58 (m, 2H), 7.47 (d, J=7.5 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 7.06-7.02 (m, 1H), 7.01-6.96 (m, 1H), 6.19 (s, 1H), 5.27 (s, 1H), 4.60 (d, J=13.8 Hz, 1H), 4.27-4.24 (m, 1H), 3.82 (s, 3H), 3.54 (s, 3H), 3.49-3.48 (m, 1H), 3.36-3.32 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 1.2: pH 8 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / benzene / 1 h / 20 °C 2.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 3.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 3.2: pH 8 4.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 20 °C 1.2: 4 h / 120 °C / Molecular sieve 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / 6 h / 0 - 40 °C 2.1: triethylamine / benzene / 1 h / 20 °C 3.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 4.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 4.2: pH 8 5.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 2.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 2.2: pH 8 3.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 20 °C 1.2: 4 h / 120 °C / Molecular sieve 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C |