CN105130927A - Phenyl-nitrogen alkadienone derivative as well as preparation method and application thereof - Google Patents

Phenyl-nitrogen alkadienone derivative as well as preparation method and application thereof Download PDF

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CN105130927A
CN105130927A CN201510577293.4A CN201510577293A CN105130927A CN 105130927 A CN105130927 A CN 105130927A CN 201510577293 A CN201510577293 A CN 201510577293A CN 105130927 A CN105130927 A CN 105130927A
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compound
preparation
derivative
nitrogen heterocyclic
nitrogen
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CN105130927B (en
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张雁冰
付冬君
张赛扬
刘宏民
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Zhengzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms

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Abstract

The invention discloses a phenyl-nitrogen alkadienone derivative as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry. Nitrogen-containing heterocycle and a chalcone parent nucleus skeleton are spliced to simply, efficiently and environment friendly synthesize a 12 phenyl-nitrogen alkadienone derivative. The phenyl-nitrogen alkadienone derivative has a general structural formula shown as follows: (see the specification), wherein R1 is a halogen element or trimethoxy; R2 is N-methyl piperazine, morpholine, imidazole, nafoxidine and piperidine. X is a halogen element or H. An in-vitro anticancer activity test of the compound proves that the derivative has an effect of inhibiting a human neuroblastoma cell line (SK-N-SH), can be used as a candidate or lead compound to be further developed and is used for preparing a drug for resisting human neuroblastoma.

Description

One class benzene connection nitrogen heterocyclic chalcone derivative and its preparation method and application
Technical field
The present invention relates to medicinal chemistry art, be specifically related to a class novel benzene connection nitrogen heterocyclic chalcone derivative, their preparation method and the application as the new anti-neuroblastoma lead compound of a class thereof.
Background technology
Neuroblastoma (neuroblastoma, NB) is a kind of embryonic malignant tumor saving rear sympathetic nervous system, is one of primary tumor threatening children's life at present.Have investigation display, the sickness rate of the neuroblastoma of less than 15 years old accounts for 10% of all childhood cancer cases, and mortality ratio accounts for 15% of all childhood cancer cases, is modal malignant tumour in age less children.Therefore, find and study the new compound effectively treating neuroblastoma or biotechnological formulation etc. there is important scientific theory meaning and clinical value.
Chalcone compounds is the natural organic-compound that a class is present in the medicinal plant such as Radix Glycyrrhizae (Glycyrrhlza), safflower (Carthamus), its basic structure is 1,3-diphenylprop ketenes, can with multiple receptors bind, in antitumor, antibacterial, anti-oxidant etc., there is biological activity widely.Meanwhile, chalcone compounds is the important intermediate of synthesis flavonoid compound, has important purposes in organic synthesis.Therefore, novel benzene connection nitrogen heterocyclic chalcone derivative is prepared and the application studying its anti-tumor aspect has great importance.
Summary of the invention
The object of the invention is to provide a class novel benzene connection nitrogen heterocyclic chalcone derivative.Another object of the present invention is to provide a kind of simple efficient, the method for the synthesis benzene connection nitrogen heterocyclic chalcone derivative of environmental protection.Another object of the present invention is to provide the application of described compound in the anti-neuroblast tumor medicine of preparation.
As follows for realizing the object of the invention technical scheme: described benzene connection nitrogen heterocyclic chalcone derivative has following general structure:
R 1for halogen or methoxyl group, preferred 4-fluorine, 4-chlorine, 4-bromine or 2,4,6-trimethoxy.
R 2for N methyl piperazine, morpholine, imidazoles, Pyrrolidine, piperidines.
X is halogen or H, the preferred F of halogen.
Compound shown in described benzene connection nitrogen heterocyclic chalcone derivative preferred formula (I-1) ~ (I-12):
Novel sulfurized alkadienone derivative of the present invention obtains mainly through the following step:
(1) preparation method of compound (III):
In solvent, by heterocyclic amine in the basic conditions with p-Fluorobenzenecarboxaldehyde or 3,4-difluorobenzaldehyde (II) is obtained by reacting compound III, and alkali used is the one in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, sodium phosphate, ten phosphate dihydrate sodium, potassiumphosphate, saleratus, sodium bicarbonate; Solvent used is the mixture of one of in ethanol, methyl alcohol, DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), dioxane or wherein any two kinds; Reaction is carried out between 0-90 DEG C.
(2) preparation method of general formula (I):
In solvent, compound (III) and substituted acetophenone react in the basic conditions, after question response completes, and condensation, separate out solid, namely suction filtration obtains general formula (I) compound; Solvent used is the mixture of one of in acetone, acetonitrile, ethanol, methyl alcohol, Virahol, distilled water or wherein any two or three; Reaction is carried out between 0-90 DEG C.
Described substituted acetophenone selects halo acetophenone or methoxyacetophenone, preferred 4-fluoro acetophenone, 4-chloro-acetophenone, 4-bromoacetophenone or 2,4,6-trimethoxy methyl phenyl ketone.
The invention has the advantages that: nitrogen heterocyclic ring and cinnamophenone parent nucleus skeleton are spliced, synthesis benzene connection nitrogen heterocyclic chalcone derivative, method is simply efficient, environmental protection.The test of such Compound ira vitro antitumour activity shows to have certain restraining effect to Human neuroblastoma cell strain (SK-N-SH), can be used as candidate or the lead compound of exploitation further, is applied to and prepares the female tumor medicine of anti human nerve.
Embodiment
The preparation of embodiment 1 compound (III)
4-fluorobenzaldehyde (10mmol) and corresponding heterocyclic amine (20mmol) are placed in container, and the DMSO then adding 30mL dissolves, 100 DEG C of reactions.TLC monitoring process, after reaction terminates, is cooled to room temperature, in system, adds saturated aqueous solution of sodium bicarbonate, be extracted with ethyl acetate 4 times, and merge organic phase, with anhydrous magnesium sulfate drying, filtering siccative, underpressure distillation obtains crude product.Crude product column chromatography, chloroform/methanol=20:1 wash-out, obtains solid pure product.
The preparation of embodiment 2 general formula (I)
By compound (III) (5mmol) and substituted acetophenone (6mmol), be dissolved in 30mL ethanol, add the distilled water of sodium hydroxide (7.5mmol) and 3mL, stirred overnight at room temperature.Underpressure distillation removing etoh solvent, residue with Ethyl acetate extracts, and washes with water, and by saturated aqueous common salt back extraction ethyl acetate phase, last organic phase anhydrous magnesium sulfate drying, mistake filters magnesium sulfate, and concentrating under reduced pressure obtains crude product.Crude product column chromatography, chloroform/methanol=8:1 wash-out, obtains ultimate aim product cinnamophenone.
I-1: yellow solid, total recovery 54%; M.p.:166-169 DEG C of .IR (KBr) cm -1: 1650,1576. 1hNMR (400MHz, CDCl 3): δ 7.93 (d, J=7.6Hz, 2H), 7.78 (d, J=15.5Hz, 1H), 7.56 (d, J=9.5Hz, 2H), 7.47 (d, J=9.3Hz, 2H), 7.34 (d, J=15.5Hz, 1H), 6.90 (d, J=7.6Hz, 2H), 3.86 (t, 4H), 3.24 (t, 4H). 13cNMR (101MHz, CDCl 3): δ 189.2,152.9,145.5,138.8,137.1,130.3,129.8,128.8,125.6,118.1,114.6,66.6,47.9.
I-2: yellow solid, total recovery 68%; M.p.:123-124 DEG C of .IR (KBr) cm -1: 1655,1590. 1hNMR (400MHz, CDCl 3): δ 7.96 (d, J=8.4Hz, 2H), 7.73 (d, J=15.5Hz, 1H), 7.48 (d, J=8.4Hz, 2H), 7.34 (d, J=15.5Hz, 1H), 7.32 (m, 2H), 6.93 (t, J=8.8Hz, 1H), 3.23 (t, 4H), 2.61 (t, 4H), 2.37 (s, 3H). 13cNMR (101MHz, CDCl 3): δ 188.9,156.3,153.9,144.2,139.1,136.7,129.8,128.9,126.2,119.8,118.6,115.3,115.1,55.0,50.0,49.9,46.1.
I-3: safran solid, total recovery 67%; M.p.:140-143 DEG C of .IR (KBr) cm -1: 1648,1576. 1hNMR (400MHz, CDCl 3): δ 7.95 (d, J=8.4Hz, 2H), 7.73 (d, J=15.5Hz, 1H), 7.46 (d, J=8.4Hz, 2H), 7.30 (d, J=15.5Hz, 1H), (7.25 m, 2H), 6.59 (t, J=8.8Hz, 1H), 3.52 (m, 4H), 1.98 (m, 4H). 13cNMR (101MHz, CDCl 3): δ 188.9,152.3,149.9,145.2,138.6,137.2,129.7,128.8,127.0,117.1,115.5,115.3,114.6,49.7,25.4.
I-4: yellow solid, total recovery 71%; M.p.:118-119 DEG C of .IR (KBr) cm -1: 1659,1594. 1hNMR (400MHz, CDCl 3): δ 7.96 (d, J=8.6Hz, 2H), 7.73 (d, J=15.5Hz, 1H), 7.48 (d, J=8.6Hz, 2H), 7.39 – 7.31 (m, 3H), 6.93 (t, J=8.7Hz, 1H), 3.93 – 3.86 (m, 4H), 3.24 – 3.15 (m, 4H). 13cNMR (101MHz, CDCl 3): δ 188.8,156.4,153.9,144.0,139.1,136.6,129.8,128.9,126.2,120.1,118.3,115.4,115.2,66.8,50.4.
I-5: safran solid, total recovery 51%; M.p.:157-158 DEG C of .IR (KBr) cm -1: 1653,1588. 1hNMR (400MHz, CDCl 3): δ 7.95 (d, J=8.5Hz, 2H), 7.78 (d, J=15.5Hz, 1H), 7.56 (d, J=8.8Hz, 2H), 7.46 (d, J=8.5Hz, 2H), 7.33 (d, J=15.5Hz, 1H), 6.91 (d, J=8.7Hz, 2H), 3.39 – 3.31 (m, 4H), 2.61 – 2.55 (m, 4H), 2.36 (s, 3H). 13cNMR (101MHz, CDCl 3): δ 189.3,152.8,145.7,138.7,137.1,130.3,129.8,128.8,125.1,117.7,114.8,54.8,47.6,46.1.
I-6: safran solid, total recovery 56%; M.p.:151-152 DEG C of .IR (KBr) cm -1: 1647,1575. 1hNMR (400MHz, CDCl 3): δ 7.95 (d, J=8.5Hz, 2H), 7.78 (d, J=15.5Hz, 1H), 7.54 (d, J=8.8Hz, 2H), 7.46 (d, J=8.5Hz, 2H), 7.30 (d, J=15.5Hz, 1H), 6.89 (d, J=8.8Hz, 2H), 3.37 – 3.29 (m, 4H), 1.67 (m, 6H). 13cNMR (101MHz, CDCl 3): δ 189.3,153.3,146.0,138.6,137.3,130.4,129.8,128.8,124.1,117.1,114.7,48.9,25.4,24.3.
I-7: safran solid, total recovery 69%; M.p.:158-159 DEG C of .IR (KBr) cm -1: 1645,1588. 1hNMR (400MHz, CDCl 3): δ 7.99 – 7.92 (m, 2H), 7.80 (d, J=15.4Hz, 1H), 7.54 (d, J=8.7Hz, 2H), 7.49 – 7.42 (m, 2H), 7.26 (d, J=15.4Hz, 1H), 6.56 (d, J=8.8Hz, 2H), 3.37 (t, J=6.6Hz, 4H), 2.10 – 2.02 (m, 4H). 13cNMR (101MHz, CDCl 3): δ 189.2,149.8,146.7,138.3,137.6,130.8,129.7,128.7,121.9,115.5,111.8,47.6,25.5.
I-8: yellow solid, total recovery 54%; M.p.:164-165 DEG C of .IR (KBr) cm -1: 1678,1598. 1hNMR (400MHz, CDCl 3): δ 7.90 (s, 1H), 7.64 (d, J=8.5Hz, 2H), 7.45 – 7.36 (m, 3H), 7.31 (s, 1H), 7.23 (s, 1H), 6.99 (d, J=16.0Hz, 1H), (6.17 s, 2H), 3.87 (s, 3H), 3.79 (s, 6H). 13cNMR (101MHz, CDCl 3): δ 193.6,162.7,159.0,141.9,138.3,135.4,134.3,130.8,129.9,129.7,121.3,117.8,111.7,90.8,56.0,55.5.
I-9: safran solid, total recovery 53%; M.p.:168-169 DEG C of .IR (KBr) cm -1: 1652,1586. 1hNMR (400MHz, CDCl 3): δ 7.87 (d, J=8.4Hz, 2H), 7.77 (d, J=15.5Hz, 1H), 7.62 (d, J=8.4Hz, 2H), 7.55 (d, J=8.7Hz, 2H), 7.30 (d, J=15.5Hz, 1H), 6.89 (d, J=8.7Hz, 2H), 3.40 – 3.27 (m, 4H), 2.62 – 2.50 (m, 4H), 2.34 (s, 3H). 13cNMR (101MHz, CDCl 3): δ 189.4,152.8,145.8,137.6,131.8,130.3,129.9,127.3,125.0,117.7,114.7,54.8,47.6,46.2.
I-10: safran solid, total recovery 69%; M.p.:167-168 DEG C of .IR (KBr) cm -1: 1633,1597. 1hNMR (400MHz, CDCl 3): δ 7.42 (d, J=8.4Hz, 2H), 7.27 (d, J=15.7Hz, 1H), 6.85 (d, J=8.4Hz, 2H), 6.81 (d, J=15.7Hz, 1H), 6.16 (s, 2H), 3.85 (s, 3H), 3.75 (s, 6H), 3.35 – 3.21 (m, 4H), 2.60 – 2.49 (m, 4H), 2.34 (s, 3H). 13cNMR (101MHz, CDCl 3): δ 194.5,162.1,158.6,152.5,144.9,129.9,125.7,125.3,114.8,113.5,90.8,55.9,55.4,54.7,47.7,46.1.
I-11: safran solid, total recovery 66%; M.p.:161-162 DEG C of .IR (KBr) cm -1: 1648,1580. 1hNMR (400MHz, CDCl 3): δ 7.87 (d, J=8.5Hz, 2H), 7.80 (d, J=15.4Hz, 1H), 7.61 (d, J=8.5Hz, 2H), 7.53 (d, J=8.7Hz, 2H), 7.24 (d, J=15.0Hz, 1H), 6.55 (d, J=8.8Hz, 2H), 3.36 (t, J=6.6Hz, 4H), 2.11 – 1.96 (m, 4H). 13cNMR (101MHz, CDCl 3): δ 189.4,149.8,146.8,138.0,131.7,130.8,129.9,127.0,121.9,115.5,111.8,47.6,25.5.
I-12: safran solid, total recovery 55%; M.p.:169-170 DEG C of .IR (KBr) cm -1: 1640,1589. 1hNMR (400MHz, CDCl 3): δ 7.39 (d, J=8.7Hz, 2H), 7.26 (d, J=15.8Hz, 1H), 6.76 (d, J=15.8Hz, 1H), 6.49 (d, J=8.8Hz, 2H), 6.16 (s, 2H), 3.85 (s, 3H), 3.75 (s, 6H), 3.32 (t, J=6.6Hz, 4H), 2.06 – 1.96 (m, 4H). 13cNMR (101MHz, CDCl 3): δ 194.6,162.0,158.6,149.4,146.4,130.4,123.8,122.0,112.5,111.6,90.8,55.9,55.5,47.6,25.4.
The female tumor activity of anti human nerve of embodiment 3 above-claimed cpd measures:
1. experimental technique:
Screening compound used therefor is all by synthesis of the present invention, purifying and obtaining; Stock sample solution: take 3-5mg sample and be placed in 1.5mLEP pipe, being then mixed with concentration with DMSO is 128 × 10 3the solution of μ g/mL, preserves for 4 DEG C and places, utilize substratum to dilute during experiment according to desired concn.
2. primary dcreening operation
The cell of taking the logarithm vegetative period, after digestion counting, cell density is adjusted with substratum, be seeded in 96 orifice plates with 4000-5000 cell/ hole, every hole 150 μ L, after cultivating 24h, discard substratum, add the medicine (50 μ g/mL, 100 μ g/mL) diluted with substratum, each concentration establishes 6 multiple holes, separately establishes blank group and negative control group.After drug effect 72h, every hole adds 20 μ LMTT, and after continuing to cultivate 4h, suck liquid, add the DMSO of 150mL, shaken well, absorbance is detected at microplate reader 490nm place, and calculate inhibiting rate, calculation formula is as follows:
Inhibiting rate (%)=(1-administration group absorbance/blank group absorbance) × 100%
3, dusting cover
The sample that during 50 μ g/mL, inhibiting rate is greater than 50%, resets concentration and carries out dusting cover.Add in 96 orifice plates by testing sample with 0.25 μ g/mL, 0.5 μ g/mL, 1 μ g/mL, 2 μ g/mL, 4 μ g/mL, 8 μ g/mL, 16 μ g/mL, 32 μ g/mL concentration, after cultivating 72h, detect.Test-results adopts SPSS computed in software IC 50value and relation conefficient.Experimental result is in table 1.
Table 1 compound suppresses the IC50 value of Human neuroblastoma cell strain (SK-N-SH)
aeach numerical value mean value ± standard deviation (mean ± SD) represents, variance analysis: p<0.05.
Experimental result shows, benzene connection nitrogen heterocyclic chalcone derivative provided by the present invention has certain restraining effect to SK-N-SH tumour cell, wherein the anti tumor activity in vitro of Compound I-8 is obviously better than 5-fluor-uracil, can be used as candidate or the lead compound of exploitation further, be applied to and prepare the female tumor medicine of anti human nerve.

Claims (4)

1. benzene connection nitrogen heterocyclic chalcone derivative, is characterized in that having general structure as follows:
R 1for 4-fluorine, 4-chlorine, 4-bromine or 2,4,6-trimethoxy;
R 2for N methyl piperazine, morpholine, imidazoles, Pyrrolidine or piperidines;
X is F or H.
2. benzene connection nitrogen heterocyclic chalcone derivative as claimed in claim 1, is characterized in that, select one of following compound:
3. benzene connection nitrogen heterocyclic chalcone derivative as claimed in claim 1 is preparing the application in medicine, it is characterized in that, by its as activeconstituents for the preparation of the female tumor medicine of anti human nerve.
4. the method for preparation benzene connection as claimed in claim 1 nitrogen heterocyclic chalcone derivative, is characterized in that, comprise the following steps:
(1) preparation method of compound (III):
In solvent, by nitrogen heterocyclic ring in the basic conditions with p-Fluorobenzenecarboxaldehyde or 3,4-difluorobenzaldehyde (II) is obtained by reacting compound III, and alkali used is the one in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, sodium phosphate, ten phosphate dihydrate sodium, potassiumphosphate, saleratus, sodium bicarbonate; Solvent used is the mixture of one of in ethanol, methyl alcohol, DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), dioxane or wherein any two kinds; Reaction is carried out between 0-90 DEG C;
(2) preparation method of general formula (I):
In solvent, compound (III) and substituted acetophenone react in the basic conditions, after question response completes, and condensation, separate out solid, namely suction filtration obtains general formula (I) compound; Solvent used is the mixture of one of in acetone, acetonitrile, ethanol, methyl alcohol, Virahol, distilled water or wherein any two or three; Reaction is carried out between 0-90 DEG C;
Described substituted acetophenone selects 4-fluoro acetophenone, 4-chloro-acetophenone, 4-bromoacetophenone or 2,4,6-trimethoxy methyl phenyl ketone.
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CN105566149B (en) * 2016-03-02 2017-05-24 郑州大学 Chalcone cationic antimicrobial peptide simulant with antimicrobial activity and preparation method thereof
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CN109232477A (en) * 2018-10-29 2019-01-18 郑州大学 Chalcone-dithiocarbamates catalase-like inhibitor and its synthetic method and application
CN109232477B (en) * 2018-10-29 2022-07-05 郑州大学 Chalcone-aminodithioformate catalase inhibitor and synthesis method and application thereof
CN109705017A (en) * 2019-01-22 2019-05-03 中美（河南）荷美尔肿瘤研究院 A kind of chalcone indole derivatives application in preparation of anti-tumor drugs
CN109705017B (en) * 2019-01-22 2022-09-20 中美（河南）荷美尔肿瘤研究院 Application of chalcone indole derivative in preparation of antitumor drugs
CN115583915A (en) * 2022-10-09 2023-01-10 云南中医药大学 Quinoline chalcone derivative, and synthesis method and application thereof

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