CN115894596B - Nitric acid ester NO donor type ginseng diol derivative and preparation method and application thereof - Google Patents

Nitric acid ester NO donor type ginseng diol derivative and preparation method and application thereof Download PDF

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CN115894596B
CN115894596B CN202211612130.1A CN202211612130A CN115894596B CN 115894596 B CN115894596 B CN 115894596B CN 202211612130 A CN202211612130 A CN 202211612130A CN 115894596 B CN115894596 B CN 115894596B
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nitric acid
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CN115894596A (en
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蒲洪
邹澄
李爱杰
赵庆
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Hunan University of Medicine
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Abstract

The invention provides a nitric acid ester NO donor type ginseng diol derivative. The nitrate compound capable of releasing high concentration NO is combined with ginseng diol by utilizing the split principle, and acts on tumor cells through double functions.

Description

Nitric acid ester NO donor type ginseng diol derivative and preparation method and application thereof
Technical Field
The invention relates to the technical field of medicines, in particular to a nitric acid ester NO donor type ginseng diol derivative.
Background
Panaxadiol (Panaxadiol) is a dammarane type triterpene sapogenin compound with cytotoxin, anti-Alzheimer disease, anti-inflammatory and cardiovascular protection pharmacological activity, and is mainly obtained by acid hydrolysis of medicinal plant saponins such as Ginseng radix, notoginseng radix, radix Panacis Quinquefolii, etc. The structure modification of the panaxadiol discovers lead compounds with stronger cytotoxic activity and anti-Alzheimer's disease activity, and has positive significance for the deep processing of the ginseng and pseudo-ginseng industries.
Malignant tumor is one of the major diseases threatening human life health, and development of novel antitumor drugs is required to treat such diseases. At present, the structural modification of panaxadiol at home and abroad mainly focuses on the modification of 3-hydroxyl, and reported fatty acid, amino acid and indole alkaloid panaxadiol derivatives all have cytotoxin active compounds which are more effective than panaxadiol, but NO NO donor type panaxadiol derivatives and NO report on anti-tumor drugs thereof exist at present.
Disclosure of Invention
In order to solve the technical problems, the invention provides a nitrate NO donor type ginseng diol derivative which has cytotoxic activity on tumor cells.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a nitrate NO donor type ginseng diol derivative, which is characterized by comprising the following structure:
。
the nitrate compound is an excellent NO donor, can release high-concentration NO in organisms, and can nitrify or nitrosate various proteins in tumor cells by forming nitrogen oxides to destroy cell structures and induce apoptosis of the tumor cells. Isosorbide mononitrate acts as a metabolite of isosorbide nitrate, acting to dilate blood vessels by releasing high concentrations of NO.
The invention relates to application of nitric acid esters NO donor type ginseng diol derivatives in preparing antitumor drugs.
Preferably, the antitumor drug is used for treating breast cancer and lung cancer.
The preparation method of the nitric acid ester NO donor type ginseng diol derivative comprises the following steps:
A. panaxadiol and CH 2 Cl 2 Fully dissolving, adding PCC, and reacting to obtain a compound 1;
B. dissolving the compound 1 in methanol, adding sodium cyanoborohydride and ammonium acetate, and reacting to obtain a compound 2;
C. mixing the compound 2, pyridine, succinic anhydride and DMAP, and reacting to obtain a compound 3;
D. compound 3, isosorbide mononitrate and CH 2 Cl 2 Mixing uniformly, adding DCC and DMAP at low temperature, and reacting at room temperature to obtain the final product.
Preferably, the reaction temperature of the step C is 50 ℃, and the reaction yield is the highest under the condition of 50 ℃.
Preferably, the low temperature of the step D is 0-4 ℃, so that the stability of the reagent is ensured.
The invention combines nitrate compounds with high concentration NO release with ginseng diol by utilizing the split principle, and the characteristics of NO endogenous existence and NO conversion into harmless ions after 6 seconds of action determine that the nitric acid compounds not only can play the efficacy, but also can furthest reduce toxic and side effects. Through dual action, acts on tumor cells.
Drawings
FIG. 1 is a carbon spectrum of Compound 3.
FIG. 2 is a carbon spectrum of Compound 4.
Detailed Description
The invention will be further described by the following examples for the purpose of more clearly and specifically describing the object of the invention. The following examples are only for specific illustration of the implementation method of the present invention and do not limit the protection scope of the present invention.
Example 1
A nitrate NO donor type ginseng diol derivative, which is characterized by comprising the following structure:
。
the preparation method of the nitric acid ester NO donor type ginseng diol derivative comprises the following steps:
A. panaxadiol and CH 2 Cl 2 Fully dissolving, adding PCC,reacting to obtain a compound 1;
B. dissolving the compound 1 in methanol, adding sodium cyanoborohydride and ammonium acetate, and reacting to obtain a compound 2;
C. mixing the compound 2, pyridine, succinic anhydride and DMAP, and reacting to obtain a compound 3;
D. compound 3, isosorbide mononitrate and CH 2 Cl 2 Mixing uniformly, adding DCC and DMAP at low temperature, and reacting at room temperature to obtain the final product.
Synthetic route
Example 2
Synthesis of Compound 1
Weighing panaxadiol (500 mg, 1eq, 1.09 mmoL) and adding into 50 mL two-necked flask, adding 15 mLCH 2 Cl 2 After sufficient dissolution, PCC (3 eq, 701.77 mg) was weighed again, 15 mLCH 2 Cl 2 After fully dissolving and uniformly stirring, rapidly adding the mixture into a two-necked flask under the condition of stirring, tracking the reaction process by using a TLC plate, reacting at room temperature for 2 h, tracking the reaction process by TLC, stopping the reaction after the raw materials disappear, rapidly filtering by using 100-200 mesh silica gel, flushing a solvent by using ethyl acetate, concentrating the ethyl acetate under reduced pressure, and purifying by using column chromatography to obtain the compound 1. Compound 1, white powder, yield 94.11%; 1 H NMR (500MHz, CDCl 3 ) δ: 0.86 (3H, s, H-19), 0.97 (3H, s, H-30), 1.00 (3H, s, H-28), 1.02 (3H, s, H-18) , 1.06 (3H, s, H-29) , 1.18 (3H, s, H-26), 1.21 (3H, s, H-27), 1.26 (3H, s, H-21), 3.52-3.57 (1H, m, CH-12); 13 C NMR (CDCl 3 , 125MHz) δ: 217.9 (C-3), 76.6 (C-20), 73.3 (C-25), 69.9 (C-12), 55.2 (C-17), 54.5 (C-13), 51.1 (C-14), 49.2 (C-9), 49.1 (C-5), 47.3 (C-4), 39.6 (C-1), 39.6 (C-8), 36.7 (C-10), 36.3 (C-24), 35.6 (C-2), 34.1 (C-22), 34.0 (C-7), 33.0 (C-27), 31.0 (C-15), 30.7 (C-11), 27.0 (C-26), 26.6 (C-29), 25.0 (C-16), 20.9 (C-28), 19.6 (C-6), 19.3 (C-21), 16.8 (C-30), 16.1 (C-23), 15.9 (C-18), 15.2 (C-19).
synthesis of Compound 2
In 500 mL flask with heating, stirring, reflux condensing tube, etc., compound 1 (1 eq, 2.5 g, 5.45 mmoL), sodium cyanoborohydride (3 eq, 1.0 g), ammonium acetate (10 eq, 4.2 g), methanol 250 mL, stirring at 30deg.C, TLC plate tracking reaction course, stopping reaction after reaction, evaporating methanol under reduced pressure, adding 40 mL water, extracting with ethyl acetate (300 mL ×3), mixing the extracts, washing with saturated sodium bicarbonate solution, distilled water, saturated salt water, anhydrous Na 2 SO 4 Drying, filtering, concentrating the filtrate, and purifying by column chromatography to obtain compound 2 (2.22. 2.22 g). White powder, yield 88.4%; 1 H NMR (400MHz, CDCl 3 ) δ: 0.73 (3H, s, H-19), 0.85 (3H, s, H-30), 0.87 (3H, s, H-28), 0.94 (3H, s, H-18), 0.97 (3H, s, H-29), 1.17 (3H, s, H-26), 1.21 (3H, s, H-27), 1.26 (3H, s, H-21), 2.34-2.36 (1H, m, CH-3), 3.48-3.55 (1H, m, CH-12); 13 C NMR (CDCl 3 , 100MHz) δ: 76.6 (C-20), 73.0 (C-25), 69.9 (C-12), 59.6 (C-3), 56.4 (C-5), 54.6 (C-17), 51.1 (C-14), 49.9 (C-9), 49.0 (C-13), 39.6 (C-8), 39.4 (C-1), 38.1 (C-4), 37.2 (C-10), 36.4 (C-24), 35.7 (C-22), 34.8 (C-7), 32.9 (C-27), 31.0 (C-15), 30.4 (C-11), 28.3 (C-26), 27.9 (C-29), 27.0 (C-2), 25.1 (C-16), 19.3 (C-21), 18.5 (C-6), 17.0 (C-30), 16.2 (C-23), 15.9 (C-18), 15.6 (C-19), 15.5 (C-28); ESI-MS(m/z): 460.4[M + 1] + .
synthesis of Compound 3
Adding compound 2 (1 eq, 50 mg, 0.11 mmoL), succinic anhydride (2 eq, 22.0 mg), DMAP (2 eq, 26.8 mg), pyridine 10 mL, heating and refluxing at 50deg.C, keeping the temperature for reaction, TLC detecting the disappearance of the raw material, vacuum evaporating to dryness, adding 30 mL water, extracting with ethyl acetate (100 mL ×3), mixing the extracts, washing with 10% hydrochloric acid 3 times and saturated salt water 3 times, and anhydrous Na 2 SO 4 Drying, filtering, concentrating filtrate, and purifying by column chromatography to obtain compound 3%21.0 mg). White powder, yield 34.1%; 1 H NMR (400MHz, CDCl 3 ) δ: 0.76(3H, s, H-19), 0.84 (3H, s, H-30), 0.87 (3H, s, H-28), 0.96 (3H, s, H-18), 1.16 (3H, s, H-29), 1.20 (3H, s, H-26)，1.25 (3H, s, H-27), 1.30 (3H, s, H-21), 2.17-2.69 (4H, m, 2×COCH 2 ), 3.55-3.56 (1H, m, CH-12), 3.61-3.66 (1H, m, CH-3); 13 C NMR (CDCl 3 , 100MHz) δ: 174.8 (C-4＇), 172.0 (C-1＇), 77.3 (C-20), 73.1 (C-25), 70.0 (C-12), 56.6 (C-3), 56.3 (C-5), 54.5 (C-17), 51.1 (C-14), 49.4 (C-9), 49.1 (C-13), 39.5 (C-8), 39.2 (C-1), 37.8 (C-4), 36.8 (C-10), 36.2 (C-24), 35.5 (C-22), 34.6 (C-7), 32.8 (C-27), 31.2 (C-15), 31.0 (C-11), 29.8 (C-3＇), 28.8 (C-26), 27.9 (C-29), 27.0 (C-2), 25.2 (C-2＇), 25.0 (C-16), 19.2 (C-21), 18.4 (C-6), 16.9 (C-30), 16.1 (C-23), 16.0 (C-18), 15.9 (C-19), 15.4 (C-28).
synthesis of NO donor type panaxadiol derivative (Compound 4)
Compound 3 (1 eq, 30mg, 0.055 mmoL), isosorbide mononitrate (2 eq, 21 mg), CH 2 Cl 2 10 Adding the solution into a 25mL two-necked flask, stirring to dissolve the solution sufficiently, adding DCC (2 eq, 22.7 mg) and DMAP (2 eq, 13.4 mg) at low temperature, reacting at 30deg.C under stirring overnight, filtering, washing with saturated salt water, and removing anhydrous Na 2 SO 4 Drying, filtering, concentrating the filtrate under reduced pressure, and purifying by column chromatography to obtain compound 4 (19.0. 19.0 mg). White powder, yield 47.1%; 1 H NMR (500MHz, CDCl 3 ) δ: 0.76 (3H, s, H-19), 0.84 (3H, s, H-30), 0.87 (3H, s, H-28), 0.88 (3H, s, H-18) , 0.97 (3H, s, H-29) ,1.17 (3H, s, H-26), 1.20 (3H, s, H-27), 1.26 (3H, s, H-21), 2.64-2.68 (4H, m, 2×COCH 2 ), 3.87-3.91 (1H, m,CH-12), 3.99-4.03 (1H, m, CH-3), 5.33-5.34 (2H, m, 2×OCH); 13 C NMR (CDCl 3 : 100MHz) δ:172.0 (C-4＇), 170.3 (C-1＇), 86.4 (C-3＂), 81.4 (C-6＂), 81.2 (C-1＂), 77.4 (C-4＂), 76.6 (C-20), 73.4 (C-5＂), 73.1 (C-25), 69.8 (C-2＂), 69.2 (C-12), 56.6 (C-3), 56.5 (C-5), 54.6 (C-17), 51.1 (C-14), 49.7 (C-9), 49.0 (C-13), 39.6 (C-8), 39.2 (C-1), 37.8 (C-4), 36.9 (C-10), 36.4 (C-24), 35.6 (C-22), 34.7 (C-7), 32.9 (C-27), 31.1 (C-15), 31.0 (C-11), 30.3 (C-3＇), 29.6 (C-2＇), 28.3 (C-26), 27.1 (C-29), 25.6 (C-2), 25.1 (C-16), 19.3 (C-21), 18.5 (C-6), 16.9 (C-30), 16.3 (C-23), 16.2 (C-18), 16.0 (C-19), 15.5 (C-28).
antitumor Activity screening
Compounds 1-4 were screened for biological activity against lung cancer cell lines (A-549) and breast cancer cell lines (MCF-7) in vitro using the MTS method, with cisplatin and paclitaxel as positive controls (Table 1). Preparing single cell suspension by using culture solution (DMEM or RMPI 1640) of 10% fetal bovine serum, inoculating 5000-10000 cells in each hole to a 96-well plate, and culturing 12 h adherent cells in advance, wherein the volume of each hole is 100 mu L; adding a compound solution to be detected (a fixed concentration of 40 mu M of primary screening, 5 concentrations of compounds with 50% inhibition of tumor cell growth are set at the concentration to enter a gradient compound screening), the final volume of each hole is 200 mu L, and 3 compound holes are set for each treatment; 37. after 48 ℃ and h ℃, carefully absorbing and removing culture supernatant in the holes, adding 20 mu L of MTS solution and 100 mu L of culture solution in each hole, and continuing to incubate for 4 h to fully perform the reaction; selecting 490 nm wavelength, reading light absorption value of each hole by enzyme-linked immunosorbent assay (Bio-Rad 680), recording the result, drawing cell growth curve by taking concentration as abscissa and cell survival rate as ordinate, calculating IC of the compound by two-point method (Reed and Muench method) 50 Values.
TABLE 1 half inhibition concentration IC of panaxadiol derivatives on tumor cell proliferation 50 (μM)
The synthesized NO donor type panaxadiol derivative compound 4 has a remarkable inhibition effect on A-549 tumor cells compared with panaxadiol, and has better biological activity on breast cancer cell lines than cisplatin.
Panaxadiol (Shanghai Si Da pharmaceutical chemical technology Co., ltd.); succinic anhydride, bSynthetic reagents such as ammonium acid, sodium cyanoborohydride, isosorbide mononitrate and the like are all of high grade purity and are purchased from Shanghai crystal pure industry Co., ltd (Allatin); pyridine chlorochromate (Pyridinium Chlorochromate, PCC), N' -Dicyclohexylcarbodiimide (DCC) and 4-Dimethylaminopyridine (DMAP) are both analytically pure, available from shanghai taitan technologies inc (hadamard); pyridine, dichloromethane (CH) 2 Cl 2 ) The methanol is analytically pure and is purchased from Chinese medicine reagent
The lung cancer cell line (A-549) and the breast cancer cell line (MCF-7) were purchased from Shanghai cell bank of China academy of sciences.
The foregoing examples merely illustrate specific embodiments of the invention, which are described in greater detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention.

Claims (5)

1. A nitrate NO donor type ginseng diol derivative, which is characterized by comprising the following structure:
。
2. use of nitric acid esters NO donor type panaxadiol derivatives according to claim 1 for the preparation of antitumor drugs.
3. Use of nitric acid esters NO donor type ginseng diol derivatives according to claim 2 for the preparation of antitumor drugs, characterized in that said antitumor drugs are used for the treatment of breast cancer and lung cancer.
4. The method for producing nitric acid ester NO donor type ginseng diol derivative according to claim 1, wherein: the method comprises the following steps:
A. panaxadiol and CH 2 Cl 2 Fully dissolving, adding PCC, and reacting to obtain a compound 1;
B. dissolving the compound 1 in methanol, adding sodium cyanoborohydride and ammonium acetate, and reacting to obtain a compound 2;
C. mixing the compound 2, pyridine, succinic anhydride and DMAP, and reacting to obtain a compound 3;
D. compound 3, isosorbide mononitrate and CH 2 Cl 2 Mixing uniformly, adding DCC and DMAP at low temperature of 0-4 ℃, and reacting at room temperature to obtain a final product;
5. the method for producing nitric acid ester NO donor type ginseng diol derivative according to claim 4, wherein: the reaction temperature of the step C is 50 ℃.
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