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A kind of compound and its preparation method and application

A compound, methyl phenyl technology, applied in the field of compound and its preparation, achieves the effect of simple synthesis process, good inhibitory activity and easy recovery

Active Publication Date: 2022-01-28
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Isophallanone is currently mainly used in flavors and fragrances, but there are few reports on its introduction into the field of medicine

Method used

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  • A kind of compound and its preparation method and application
  • A kind of compound and its preparation method and application
  • A kind of compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 2-(4′-fluorobenzoyl)-3-(4′-fluorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a - Preparation of octahydro-5a,8-methanobenzo[g]indazole (compound 1):

[0025]

[0026] Add 3-(4′-fluorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-octahydro- 5a,8-Methylenebenzo[g]indazole (6mmol), triethylamine (9mmol) and anhydrous DCM (20mL), add p-fluorobenzoyl chloride (8mmol) dropwise at room temperature, after the addition Reacted at room temperature for 6 hours, and GC detected that the reaction was complete; after the reaction was completed, 30 mL of distilled water was added, extracted 3 times with 30 mL of ethyl acetate, the organic layers were combined, concentrated, and recrystallized from ethyl acetate / petroleum ether to obtain a yellow solid powder 2-(4 '-Fluorobenzoyl)-3-(4'-fluorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-octahydro- 5a,8-Methylene benzo[g]indazole, the yield is 69.5%. 1 H NMR (600MHz, Chloroform-d) δ8.09(d, J=8.8, 5.5Hz, 2H), 7.33(d, J=8.6, 5.4Hz,...

Embodiment 2

[0028] 2-(4′-fluorobenzoyl)-3-(4′-chlorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a - Preparation of octahydro-5a,8-methanobenzo[g]indazole (compound 2):

[0029]

[0030] The preparation method is the same as in Example 1, wherein, 3-(4'-chlorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-eight Hydrogen-5a,8-methanobenzo[g]indazole in place of 3-(4′-fluorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7 ,8,9,9a-octahydro-5a,8-methanobenzo[g]indazole, product 2-(4′-fluorobenzoyl)-3-(4′-chlorophenyl)- 5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-octahydro-5a,8-methanobenzo[g]indazole as yellow solid powder , yield 72.8%. 1 H NMR (600MHz, Chloroform-d) δ: 8.11 (dd, J = 8.9, 5.4Hz, 2H), 7.40 (d, J = 8.5Hz, 2H), 7.29 (d, J = 8.5Hz, 2H), 7.13 (t,J=8.7Hz,2H),2.47(d,J=15.8Hz,1H),2.37(s,1H),2.15(d,J=15.9Hz,1H),1.88–1.92(m,1H) ,1.81(s,1H),1.73–1.78(m,1H),1.64(d,J=10.0Hz,1H),1.50–1.56(m,1H),1.27(d,J=10.0Hz,1H), 1.24(s,3H),1.17–1.22(m,1H),1.05(s,3H),0.88(s,3H),0.77(s,3H); HR-MS (ESI + )m / z: c...

Embodiment 3

[0032] 2-(4′-fluorobenzoyl)-3-(4′-methylphenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9, Preparation of 9a-octahydro-5a,8-methanobenzo[g]indazole (compound 3):

[0033]

[0034]The preparation method is the same as in Example 1, wherein, 3-(4'-methylphenyl)-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a- Octahydro-5a,8-methanobenzo[g]indazole replacing 3-(4′-fluorophenyl)-5,5,9,9-tetramethyl-4,5,5a,6, 7,8,9,9a-octahydro-5a,8-methanobenzo[g]indazole, product 2-(4′-fluorobenzoyl)-3-(4′-methylphenyl )-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-octahydro-5a,8-methanobenzo[g]indazole is yellow Solid powder, yield 67.8%. 1 H NMR (600MHz, Chloroform-d) δ: 8.11 (dd, J = 8.8, 5.6Hz, 2H), 7.24 (d, J = 3.3Hz, 4H), 7.12 (t, J = 8.7Hz, 2H), 2.48 (d,J=15.8Hz,1H),2.40(s,3H),2.37(s,1H),2.20(d,J=15.8Hz,1H),1.88–1.94(m,1H),1.80(s, 1H),1.74–1.78(m,1H),1.66(d,J=9.9Hz,1H),1.50–1.56(m,1H),1.27(d,J=9.9Hz,1H),1.24(s,3H ),1.17–1.22(m,1H),1.04(s,3H),0.89(s,3H),0.78(s,3H); HR-MS (ESI + )m / z: calculated for C 30...

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Abstract

The invention discloses a compound, its preparation method and application. The present invention uses isolongifolanone derivatives 3-aryl-5,5,9,9-tetramethyl-4,5,5a,6,7,8,9,9a-octahydro-5a,8- The isolongylyl indazoles were prepared from endomethylene benzo[g]indazole as raw material and acylating reagent with aroyl chloride. The anti-tumor activity of the synthesized compounds was tested, and the results showed that the prepared compounds had good inhibitory activity on human breast cancer cell MCF-7, human lung cancer cell A549 and human cervical cancer cell Hela, and had good Antitumor medicinal value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and drug synthesis, and relates to a compound and its preparation method and application. Background technique [0002] Tumor has always been the number one killer that endangers human health and life, so the development of anti-tumor drugs is the focus of new drug research and development. Since ancient times, natural products have been a treasure trove of medicines that humans have used to find relief from ailments. With the rapid development of science and technology, people's understanding of the structure and biological activity of natural products is constantly deepening, from the direct use of natural products, to the introduction of chemical small molecule functional groups to modify natural products, and then to the introduction of total synthesis strategy imitation Nature produces biologically active substances. It is precisely because of this uniqueness of natural products t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/54A61P35/00
CPCC07D231/54A61P35/00
Inventor 王石发王芸芸赵雨珣张成龙徐徐杨益琴王忠龙
Owner NANJING FORESTRY UNIV
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