Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
A compound, the technology of periodontitis, applied in the application field of preparation of drugs for the prevention and treatment of periodontitis, can solve problems such as different cytotoxicity
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Embodiment 1
[0024] The synthesis of embodiment 1 compound
[0025] Dissolve 1mmol benzaldehyde and different intermediate bridging ketones in 10-20mL absolute ethanol, add 5-10 drops of 40% NaOH solution, react at room temperature for 5-24h, and synthesize 13 skeleton compounds. Dissolve 1 mmol of benzaldehyde with different substituents and cyclopentanone or pyrone in 10-20 mL of absolute ethanol, add 5-10 drops of 40% NaOH solution, react at room temperature for 5-24 hours or add 3-5 drops of concentrated sulfuric acid , after heating in an oil bath at 78°C, two series of monocarbonyl curcumin reference compounds and effective compounds were synthesized. The progress of the reaction was checked by TLC. After the reaction, extraction, silica gel mixing sample was purified by silica gel column chromatography to obtain the target compound, and its physical and chemical properties are as follows:
[0026] Skeleton compound: 2,5-di((E)-benzylidene)cyclopentan-1-one(A). Light yellow powder,...
specific Embodiment approach
[0038] Specific embodiments: 3,5-di((E)-benzylidene)-1-cyclopropylpiperidin-4-one(M).Light yellow powder, 88.1% yield, m.p.144.8-147.6℃. 1 H NMR (600MHz, CDCl 3 ),δ:7.81(s,2H,α-H×2),7.45(d,J=2.2Hz, 4H,Ar-H 2 ,Ar-H 2’ ,Ar-H 6 ,Ar-H 6’ ),7.44(s,4H,Ar-H 3 ,Ar-H 3’ ,Ar-H 5 ,Ar-H 5’ ),7.40–7.37(m,2H,Ar-H 4 ,Ar-H 4’ ), 4.01(s,4H,CH 2 ×2),0.56–0.38(m,5H,CH 2 ×2,CH).LC-MS m / z:316.2(M+H) + , calcd for C 22 h 21 NO: 315.16.
[0039] Skeleton compound: 2,4-di((E)-benzylidene)-8-methyl-8-azabicyclo[3.2.1]octan-3-one(N).Light yellow powder,84.2%yield,m.p.144.6-146.0℃ . 1 H NMR (600MHz, CDCl 3 ),δ:7.85(s,2H,α-H×2),7.45–7.42 (m,4H,Ar-H 2 ,Ar-H 2’ ,Ar-H 6 ,Ar-H 6’ ), 7.40 (d, J=7.3Hz, 4H, Ar-H 3 ,Ar-H 3’ ,Ar-H 5 ,Ar-H5’ ),7.38–7.32(m,2H, Ar-H 4 ,Ar-H 4’ ), 4.42(s,2H,CH×2), 2.67–2.58(m,2H,CH×2), 2.32(s,3H,CH 3 ), 2.04(d, J=7.3Hz, 2H, CH×2). LC-MS m / z: 316.2(M+H) + , calcd for C 22 h 21 NO: 315.16.
[0040] Comparative compound: 2,5-bis((E)-3,4-dimethoxybenzyliden...
Embodiment 2
[0054] Example 2 Cytotoxicity screening of different monocarbonyl curcumin skeleton structures, and antioxidant activity screening of two series of monocarbonyl curcumin
[0055] In order to develop effective and less toxic MACA scaffolds, 13 MCAC scaffolds (compounds A–N) with different intermediate bridge ketones were systematically synthesized in this study. The synthesis steps are shown in Example 1, and the structure and screening results are shown in ( figure 1 A and B). The results showed that MC3T3-E1 retained its activity after being treated with compounds A (containing cyclopentanone) and H (containing pyrone) at concentrations of 20 and 60 μM for 72 hours ( figure 1C and D), showing obvious biosafety compared with native curcumin.
[0056] According to the above results, a series of compounds A (1A to 10A) and H (1H to 10H) were synthesized respectively ( figure 2 A). , after pre-incubation of MC3T3-E1 with compound (10 μM), it was subsequently exposed to 300...
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