11-(2, 4-dichlorophenyl) 12H-benzo[f]-furan [3, 4-b] chromene-10(11H)-ketone and synthetic method thereof

Abstract

The invention provides an 11-(2, 4-dichlorophenyl) 12H-benzo[f]-furan [3, 4-b] chromene-10(11H)-ketone and a synthetic method thereof. The synthetic method comprises the steps of: uniformly mixing 2- naphthol, 2, 4- dichlorobenzaldehyde, tetronic acid and catalyst amount of p-toluenesulfonic acid, heating and stirring, controlling the temperature at 110-130 DEG C and reacting for 3-5 hours. According to the invention, chlorine atoms are added in the 11-(2, 4-dichlorophenyl) 12H-benzo[f]-furan [3, 4-b] chromene-10(11H)-ketone to ensure that the 11-(2, 4-dichlorophenyl) 12H-benzo[f]-furan [3, 4-b] chromene-10(11H)-ketone has stronger activity and is more beneficial to absorption. The synthetic method provided by the invention has the characteristics of green environmental protection, easiness in obtaining raw material, simpleness in operation and high yield.

Description

[0001] technical field

[0002] The present invention relates to a kind of furo[3,4- b ] chromene derivatives, specifically, the compound 11-(2,4-dichlorophenyl) 12 H -Benzo[ f ]furo[3,4- b ]chromene-10(11 H )-ketone. Background technique

[0003] Malignant tumors are a serious threat to human health. Conquering and curing malignant tumors has become one of the hot spots in drug research around the world. Finding highly efficient, low-toxic and specific anti-tumor drugs is still the main direction of anti-tumor drug research. It has been reported in the literature that furochromene compounds have various biological activities such as antitumor, anti-inflammatory and antibacterial. In addition, studies have shown that 5 H -Furo[3,2-g]chromene compounds have strong inhibitory effect on human osteosarcoma cells.

[0004] Due to their unique physical, chemical properties and biological activity, chlorine-containing organic compounds are used in many medicines, such as th...

Examples

Embodiment 1

[0022] Put 1.44 g 2-naphthol, 1.75 g 2,4-dichlorobenzaldehyde, 1.00 g quaternary keto acid and 0.1 g p-toluenesulfonic acid in a 50 ml reaction flask and mix well, heat and stir, and control the temperature at 110 ℃ , After 4 hours of reaction. The reaction mixture was dissolved in 20 ml of dichloromethane, washed twice with 20 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl )12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 3.13 g, the yield was 82%.

[0023] After testing, the product molecular formula: C 21 H 12 Cl 2 O 3 , Molecular weight: 382.02, appearance: white solid, melting point: 242-243°C.

[0024] IR (KBr) ν : 3042, 2965, 2425, 1762, 1699, 1402, 1198, 1020, 1012, 842, 792, 742 cm -1 ; 1 H NMR (CDCl 3 , 400 MHz) δ : 7.92-7.79 (m, 2H, ArH), 7.72-7.67 (m, 1H, ArH), 7.54-7.30 (m, 4H, ArH), 7.21-6.95 (m, 2H, ArH), 5.97 (s, 1H) , C...

Embodiment 2

[0026] Put 14.4 g 2-naphthol, 19.3 g 2,4-dichlorobenzaldehyde, 10.0 g quaternary keto acid and 1 g p-toluenesulfonic acid in a 250 ml reaction flask, mix well, heat and stir, and control the temperature at 120 ℃ , After 3 hours of reaction. The reaction mixture was dissolved in 200 ml of dichloromethane, washed twice with 200 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl ) 12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 32.5 g, the yield is 85%.

Embodiment 3

[0028] Place 144 g 2-naphthol, 210 g 2,4-dichlorobenzaldehyde, 100 g quaternary ketone acid and 10 g p-toluenesulfonic acid in a 1000 ml reaction flask and mix well, heat and stir, and control the temperature at 130 ℃ , After 3.5 hours of reaction. The reaction mixture was dissolved in 2000 ml of dichloromethane, washed twice with 2000 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl )12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 317g, the yield was 83%.

[0001] technical field

[0002] The present invention relates to a kind of furo[3,4- b ] chromene derivatives, specifically, the compound 11-(2,4-dichlorophenyl) 12 H -Benzo[ f ]furo[3,4- b ]chromene-10(11 H )-ketone. Background technique

[0003] Malignant tumors are a serious threat to human health. Conquering and curing malignant tumors has become one of the hot spots in drug research around the world. Finding highly efficient, low-toxic and specific anti-tumor drugs is still the main direction of anti-tumor drug research. It has been reported in the literature that furochromene compounds have various biological activities such as antitumor, anti-inflammatory and antibacterial. In addition, studies have shown that 5 H -Furo[3,2-g]chromene compounds have strong inhibitory effect on human osteosarcoma cells.

[0004] Due to their unique physical, chemical properties and biological activity, chlorine-containing organic compounds are used in many medicines, such as th...

Examples

Embodiment 1

[0022] Put 1.44 g 2-naphthol, 1.75 g 2,4-dichlorobenzaldehyde, 1.00 g quaternary keto acid and 0.1 g p-toluenesulfonic acid in a 50 ml reaction flask and mix well, heat and stir, and control the temperature at 110 ℃ , After 4 hours of reaction. The reaction mixture was dissolved in 20 ml of dichloromethane, washed twice with 20 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl )12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 3.13 g, the yield was 82%.

[0023] After testing, the product molecular formula: C 21 H 12 Cl 2 O 3 , Molecular weight: 382.02, appearance: white solid, melting point: 242-243°C.

[0024] IR (KBr) ν : 3042, 2965, 2425, 1762, 1699, 1402, 1198, 1020, 1012, 842, 792, 742 cm -1 ; 1 H NMR (CDCl 3 , 400 MHz) δ : 7.92-7.79 (m, 2H, ArH), 7.72-7.67 (m, 1H, ArH), 7.54-7.30 (m, 4H, ArH), 7.21-6.95 (m, 2H, ArH), 5.97 (s, 1H) , C...

Embodiment 2

[0026] Put 14.4 g 2-naphthol, 19.3 g 2,4-dichlorobenzaldehyde, 10.0 g quaternary keto acid and 1 g p-toluenesulfonic acid in a 250 ml reaction flask, mix well, heat and stir, and control the temperature at 120 ℃ , After 3 hours of reaction. The reaction mixture was dissolved in 200 ml of dichloromethane, washed twice with 200 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl ) 12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 32.5 g, the yield is 85%.

Embodiment 3

[0028] Place 144 g 2-naphthol, 210 g 2,4-dichlorobenzaldehyde, 100 g quaternary ketone acid and 10 g p-toluenesulfonic acid in a 1000 ml reaction flask and mix well, heat and stir, and control the temperature at 130 ℃ , After 3.5 hours of reaction. The reaction mixture was dissolved in 2000 ml of dichloromethane, washed twice with 2000 ml of water, dried with anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white product 11-(2,4-dichlorophenyl )12 H -Benzo[ f ]Furo[3,4- b ]Chromene-10(11 H )-Ketone 317g, the yield was 83%.