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CAS No. : | 56293-29-9 | MDL No. : | |
Formula : | C15H24N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 232.36 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.87 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 78.82 |
TPSA : | 15.27 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 3.01 |
Log Po/w (XLOGP3) : | 1.59 |
Log Po/w (WLOGP) : | 1.41 |
Log Po/w (MLOGP) : | 2.74 |
Log Po/w (SILICOS-IT) : | 1.84 |
Consensus Log Po/w : | 2.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.28 |
Solubility : | 1.21 mg/ml ; 0.00522 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.52 |
Solubility : | 6.99 mg/ml ; 0.0301 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.26 |
Solubility : | 1.27 mg/ml ; 0.00548 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 4.45 |
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 |
---|---|---|
77% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetra-(n-butyl)ammonium iodide; In acetonitrile;Reflux; | General procedure: A solution of 2a?j (1 mmol) in MeCN (20 mL) was treated with <strong>[56293-29-9]aloperine</strong> (0.25 g, 1.1 mmol) and (C4H9)4N+I? (10 mg), stirred, refluxed for 10?15 h (end of reaction determined by TLC), and cooled. The resulting precipitate was filtered off and crystallized from i-PrOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium iodide; In acetonitrile; at 20℃; | General procedure: Take <strong>[56293-29-9]aloperine</strong> (1) 0.5 g (0,002 mol),Was added to 20 ml of acetonitrile, and 1.8 g (0.006 mol) of anhydrous potassium carbonate and substituted bromobenzyl or benzyl chloride (0.003 mol) were successively added to the reaction solution, followed by stirring at room temperature.TLC was detected until the reaction was complete. The organic phase was concentrated and evaporated to dryness. The solvent was dissolved in dichloromethane and washed successively with water and saturated brine. The methylene chloride layer was dried and the solvent was evaporated to dryness with a rotary evaporator to give the crude 12-N-benzyl <strong>[56293-29-9]aloperine</strong> derivative. The solution was dissolved in 20 ml of methylene chloride solventAnd then separated by column chromatography to give pure product of 12-N-benzyl-<strong>[56293-29-9]aloperine</strong> derivative (2). The resulting compound was dissolved in 5 ml of ether,And then with 1N HCl / Et2O adjusted PH = 6-7, filtered, 12-N-benzyl ether alkalis derivatives pure hydrochloric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: At 0 ° C,Take buprofezin(1) 0.5 g (0.002 mol)Was added to 20 ml of dichloromethane, And then to the reaction solution 1.8 g (0.006 mol) of anhydrous potassium carbonate and the substituted benzenesulfonyl chloride or benzoyl chloride (0.0018 mol) were successively added, and the mixture was stirred at room temperature mix. TLC was detected until the reaction was complete. Organic phase concentrated evaporated, add methylene chloride solvent dissolved, followed by water, saturated salt water washing. Drying the dichloromethane layer and evaporating the solvent with a rotary evaporator to obtain a crude product of a 12-N acyl or sulfonylsuccinate derivative, Add 20ml methylene chloride solvent dissolved, mixed with silica gel, and then by column chromatography separation, to be 12-N-acyl or sulfonyl-podic acid pure 3Or 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Take <strong>[56293-29-9]aloperine</strong> (1) 0.5 g (0,002 mol),Was added to 20 ml of acetonitrile, and 1.8 g (0.006 mol) of anhydrous potassium carbonate and substituted bromobenzyl or benzyl chloride (0.003 mol) were successively added to the reaction solution, followed by stirring at room temperature.TLC was detected until the reaction was complete. The organic phase was concentrated and evaporated to dryness. The solvent was dissolved in dichloromethane and washed successively with water and saturated brine. The methylene chloride layer was dried and the solvent was evaporated to dryness with a rotary evaporator to give the crude 12-N-benzyl <strong>[56293-29-9]aloperine</strong> derivative. The solution was dissolved in 20 ml of methylene chloride solventAnd then separated by column chromatography to give pure product of 12-N-benzyl-<strong>[56293-29-9]aloperine</strong> derivative (2). The resulting compound was dissolved in 5 ml of ether,And then with 1N HCl / Et2O adjusted PH = 6-7, filtered, 12-N-benzyl ether alkalis derivatives pure hydrochloric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With calcined ground potash; In N,N-dimethyl-formamide; at 60℃; for 3.0h; | A solution of 2-fluoro-5-nitrobenzaldehyde (7, 3.82 g, 0.022 mol) infreshly distilled DMF (12 mL) was treated with freshly calcined ground potash (3.45 g, 0.025 mol) and <strong>[56293-29-9]aloperine</strong> (1, 4.64 g,0.02 mol), heated to 60°C, stirred for 3 h, cooled to room temperature, and poured into H2O (100 mL). The resulting precipitate was filtered off and rinsed thoroughly with H2O. The crude product was removed from the filter, treated with H2O (50 mL) with added AcOH (4 mL), and stirred for 15 min. The insoluble precipitate was separated by filtration and discarded. The filtrate was made basic (pH 9) with NH4OH (25percent). The resulting precipitate was filtered off, rinsed with H2O, and driedin a vacuum desiccator over KOH to afford 8 (6.17 g) as a finely crystalline yellow powder in 81percent yield; mp 71?73°C, Rf 0.39(EtOAc?NEt3, 10:1), C22H27N3O3.1 NMR spectrum (400 MHz, DCl3, , ppm, J/Hz): 1.42 (4, m, -10, 10, 11, H-11), 1.60 (2H, m, -9, 9),1.79 (2, m, -3, 3), 1.89 (1, m, -15), 2.01 (2, m, -17, 17), 2.09 (1, m, -7), 2.20 (1, m, -4), 2.30 (1, m,-4), 2.33 (1, m, J = 11.5, -14), 2.43 (2, m, H2-12), 2.54 (1, m, H-8), 2.71 (1, m, J = 11.5, -14), 2.99 (1, m,J = 14.5, -2), 3.35 (1, m, J = 14.5, -2), 4.05 (1, d, J = 4.6, H-16), 5.75 (1, d, J = 5.5, H-6), 7.44 (1, d, J = 8.9,H-19), 8.37 (1, dd, J = 8.9, 2.3, H-20), 8.71 (1, d, J = 2.3, H-22), 10.33 (1, s, -24). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3a-b or 4a-e. 5.1.2.1. 12N-30,50-dichlorobenzoyl <strong>[56293-29-9]aloperine</strong> (3a). Yield: 85percent; whitesolid; mp 63e65 C; 1H NMR (500 MHz, DMSO-d6) d 7.69 (s, 1H),7.45 (d, J 1.9 Hz, 2H), 5.62 (d, J 3.6 Hz, 1H), 4.64 (s, 1H),3.54e3.50 (m, 1H), 3.16e3.14 (m, 1H), 3.06e3.03 (m, 1H), 2.80 (d,J 13.0 Hz, 1H), 2.67e2.62 (m, 1H), 2.54e2.52 (m, 2H), 2.40 (s, 1H),2.19 (d, J 6.8 Hz, 2H), 1.95 (s, 1H), 1.86e1.80 (m, 4H), 1.66e1.53 (m,3H), 1.40e1.35 (m, 1H), 1.07e1.02 (m, 2H). 13C NMR (126 MHz,DMSO-d6) d 166.8, 140.5, 135.3, 134.4, 128.7, 127.7, 125.0 (3), 58.7,58.1, 53.6, 46.0, 43.0, 34.3, 30.8, 27.2, 25.7, 24.4, 24.1, 23.3, 18.7.HRMS: calcd for C22H27N2OCl2 [MH]: 405.1495, found: 405.1494. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate; In acetonitrile; at 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. 5.1.1.1. 12N-p-dichlorobenzyl <strong>[56293-29-9]aloperine</strong> (2a). Yield: 73percent; yellowsolid; mp 113e115 C; 1H NMR (500 MHz, CDCl3) d 7.28e7.26 (m,2H), 7.22 (d, J 8.4 Hz, 2H), 5.58 (d, J 5.3 Hz, 1H), 4.08 (d,J 13.7 Hz, 1H), 2.98 (d, J 13.7 Hz, 1H), 2.80e2.72 (m, 4H),2.68e2.62 (m, 2H), 2.24e2.15 (m, 2H), 2.04e1.76 (m, 6H), 1.58e1.43(m, 6H),1.35e1.26 (m, 2H). 13C NMR (126 MHz, CDCl3) d 138.4,133.7,132.5, 130.2 (2), 128.6 (2), 128.4, 65.9, 65.2, 57.3, 56.1, 52.7, 52.0,35.8, 33.9 (2), 33.0, 29.7, 25.8, 25.4, 23.7. HRMS: calcd forC22H30N2Cl [MH]: 357.2092, found: 357.2099. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in acetonitrile (20 mL), and the substituted benzylhalide (3.0 mmol) was added. The reaction mixture was stirred atroom temperature for 1e2 h until TLC analysis showed completionof the reaction. Then the solvent was evaporated under reduced pressure. The gained residuewas dissolved in dichloromethane andwashed successively withwater (20 mL), brine (20 mL). The organiclayer was concentrated and purified by flash column chromatographyon silica gel with CH2Cl2/CH3OH as the eluent to give targetcompounds 2aei in free form or in acidified form by a followingtreatment with 3 N hydrochloride/ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol; at 20℃; for 12.0h; | General procedure: A solution of 1.1 mM amine in methanol (2 mL) was added under stirring to a solution of 1 mM lactone (I) in methanol (5 mL) and allowed to stand at room temperature; the degree of conversion of initial lactone was monitored by TLC. If the product did not precipitate from the reaction mixture, the solvent was evaporated in vacuo after the termination of the reaction,and the residue was recrystallized from the appropriate solvent (usually a mixture of benzene with hexane).The following compounds were obtained by this method. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 4.2.4 General procedures for the synthesis of 12N-carbamoyl aloperines (15a-d) General procedure: To a solution of aloperine (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, after the addition of triethylamine (2.4mmol), the different substituted isocyanates (2mmol) were respectively added slowly. After 30min, reaction was warmed to r.t. and stirred for 0.5h. The gained mixture was concentrated to give a residue, which was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to get the title compounds 15a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 4.2.4 General procedures for the synthesis of 12N-carbamoyl aloperines (15a-d) General procedure: To a solution of aloperine (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, after the addition of triethylamine (2.4mmol), the different substituted isocyanates (2mmol) were respectively added slowly. After 30min, reaction was warmed to r.t. and stirred for 0.5h. The gained mixture was concentrated to give a residue, which was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to get the title compounds 15a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 4.2.4 General procedures for the synthesis of 12N-carbamoyl aloperines (15a-d) General procedure: To a solution of aloperine (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, after the addition of triethylamine (2.4mmol), the different substituted isocyanates (2mmol) were respectively added slowly. After 30min, reaction was warmed to r.t. and stirred for 0.5h. The gained mixture was concentrated to give a residue, which was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to get the title compounds 15a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: <i>N</i>-(4-fluoro-phenyl)-glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-aloperine In dichloromethane at 0 - 20℃; for 12h; | General procedure: To a solution of 13a-r (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, N-hydroxy benzotrizol (HOBt, 2.7mmol), diisopropylethylamine (5.2mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI, 4mmol) were added. The mixture was stirred for 30min before the addition of aloperine (2.1mmol), and was warmed to r.t. and stirred for 12h. The mixture was washed with water and brine (30mL), dried over anhydrous Na2SO4, filtered and then the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the products 14a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(3-fluorophenylamino)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-aloperine In dichloromethane at 0 - 20℃; for 12h; | General procedure: To a solution of 13a-r (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, N-hydroxy benzotrizol (HOBt, 2.7mmol), diisopropylethylamine (5.2mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI, 4mmol) were added. The mixture was stirred for 30min before the addition of aloperine (2.1mmol), and was warmed to r.t. and stirred for 12h. The mixture was washed with water and brine (30mL), dried over anhydrous Na2SO4, filtered and then the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the products 14a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(4-chlorophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-aloperine In dichloromethane at 0 - 20℃; for 12h; | General procedure: To a solution of 13a-r (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, N-hydroxy benzotrizol (HOBt, 2.7mmol), diisopropylethylamine (5.2mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI, 4mmol) were added. The mixture was stirred for 30min before the addition of aloperine (2.1mmol), and was warmed to r.t. and stirred for 12h. The mixture was washed with water and brine (30mL), dried over anhydrous Na2SO4, filtered and then the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the products 14a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N‐(4-bromophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-aloperine In dichloromethane at 0 - 20℃; for 12h; | General procedure: To a solution of 13a-r (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, N-hydroxy benzotrizol (HOBt, 2.7mmol), diisopropylethylamine (5.2mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI, 4mmol) were added. The mixture was stirred for 30min before the addition of aloperine (2.1mmol), and was warmed to r.t. and stirred for 12h. The mixture was washed with water and brine (30mL), dried over anhydrous Na2SO4, filtered and then the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the products 14a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: <i>N</i>-(3-trifluoromethyl-phenyl)-glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-aloperine In dichloromethane at 0 - 20℃; for 12h; | General procedure: To a solution of 13a-r (2mmol) in anhydrous CH2Cl2 (30mL) at 0°C, N-hydroxy benzotrizol (HOBt, 2.7mmol), diisopropylethylamine (5.2mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI, 4mmol) were added. The mixture was stirred for 30min before the addition of aloperine (2.1mmol), and was warmed to r.t. and stirred for 12h. The mixture was washed with water and brine (30mL), dried over anhydrous Na2SO4, filtered and then the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the products 14a-r. |