AZD8055 derivative containing 5-amino-2, 6-piperidinedione and application of AZD8055 derivative

Abstract

The invention relates to the technical field of regulation and control of crop seed vigor, in particular to a 5-amino-2, 6-piperidinedione-containing AZD8055 derivative and application thereof.The 5-amino-2, 6-piperidinedione-containing AZD8055 derivative is of a chemical structure shown in a general formula (I): # imgabs0 #. The AZD8055 derivative can effectively improve the seed vigor and promote rapid germination of seeds, and then seedlings emerge robustly and consistently.

Description

Technical Field

[0001] The invention relates to the technical field of regulating and controlling the vitality of crop seeds, and in particular to an AZD8055 derivative containing 5-amino-2,6-piperidinedione and a use thereof. Background Art

[0002] The process of seed dormancy and germination is a complex life phenomenon, involving gene expression regulation, environmental signal sensing, and the synergistic effects of multiple biochemical pathways. Seed dormancy is regulated by both genetic factors and environmental factors. From a genetic perspective, there are differences in the characteristics of seed dormancy between different plant species, varieties, and ecotypes, which are mainly determined by their genetic genes. For example, the DOG1 gene of Arabidopsis thaliana is the main regulator of seed dormancy, and its expression and function are genetically regulated. Environmental factors such as temperature, light, and water also have a significant effect on seed dormancy. Temperature is the most important environmental factor affecting seed dormancy and germination. A warm environment usually accelerates the release of seed dormancy and promotes seed germination, while a low temperature keeps the seeds in a dormant state. At present, the vitality of seed germination is mainly improved by environmental conditions, which is inefficient and cannot be operated quickly. Summary of the invention

[0003] The object of the present invention is to avoid the deficiencies in the prior art and provide an AZD8055 derivative containing 5-amino-2,6-piperidindione and its use, wherein the AZD8055 derivative can effectively enhance seed vigor, promote rapid seed germination, and then produce robust and uniform seedlings.

[0004] To achieve the above object, the present invention provides the following technical solutions:

[0005] Provided is an AZD8055 derivative containing 5-amino-2,6-piperidindione, which has a chemical structure shown in general formula (I):

[0006]

[0007] Provided is the use of the above AZD8055 derivative containing 5-amino-2,6-piperidindione in improving the vitality of crop seeds.

[0008] In some embodiments, the seeds are crop seeds.

[0009] In some embodiments, the crop seeds include rice, sweet corn, soybean, tomato, cucumber, water spinach, and Chinese cabbage.

[0010] In some embodiments, the crop seeds are rice or corn.

[0011] Provided is the use of the above AZD8055 derivative containing 5-amino-2,6-piperidindione in preparing a medicine for improving the vitality of crop seeds.

[0012] In some embodiments, the drug is administered by mixing the drug with seeds and allowing the seeds to germinate and grow.

[0013] In some embodiments, the concentration of the AZD8055 derivative containing 5-amino-2,6-piperidindione in the medicament is 2 μM.

[0014] A pharmaceutical composition is provided which contains the above-mentioned 5-amino-2,6-piperidindione-containing AZD8055 derivative as an active ingredient and one or more pharmaceutically acceptable excipients.

[0015] The beneficial effects of the AZD8055 derivative containing 5-amino-2,6-piperidindione and its use in the present invention are as follows:

[0016] The present invention has found through research that the AZD8055 derivative containing 5-amino-2,6-piperidinyldione can not only improve the vitality of crop seeds, but also has a more excellent effect of improving crop seeds than the AZD8055 compound; wherein, the AZD8055 derivative containing 5-amino-2,6-piperidinyldione comprises pyrido [2,3-D] pyrimidine and 4-methoxy-phenyl, which can achieve the regulation of ABA (plant hormone abscisic acid) signal pathway, which can then effectively improve the vitality of crop seeds, promote rapid germination of seeds and robust and consistent emergence of seedlings; containing 5-amino-2,6-piperidinyldione group can improve the vitality of crop seeds based on its acidity, and the application of 5-amino-2,6-piperidinyldione in improving seed activity is developed, which is suitable for large-scale production and application. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 This is the test of the improvement effect of AZD8055 derivatives containing 5-amino-2,6-piperidindione on the germination rate of seeds of different rice varieties in Experimental Example 1.

[0018] Figure 2 This is the experimental example 2, which tests the treatment effect of AZD8055 derivatives containing 5-amino-2,6-piperidindione on the germination rate and seedling rate of corn seeds.

[0019] Figure 3 This is a test of the treatment effect of the derivatives of Experimental Example 3 on the germination rate and seedling rate of corn seeds stored for one year.

[0020] Figure 4 It is a schematic diagram of the basic skeleton of AZD8055. DETAILED DESCRIPTION

[0021] The preferred embodiments of the present invention will be described in more detail below with reference to the accompanying drawings. Although the preferred embodiments of the present invention are shown in the accompanying drawings, it should be understood that the present invention can be implemented in various forms and should not be limited by the embodiments described herein. On the contrary, these embodiments are provided to make the present invention more thorough and complete, and to fully convey the scope of the present invention to those skilled in the art.

[0022] Example 1

[0023] To illustrate the method for obtaining the AZD8055 derivative containing 5-amino-2,6-piperidindione of the present invention, the following contents are disclosed:

[0024] like Figure 4 The basic skeleton of the AZD8055 compound shown in the figure, wherein basic skeleton 1 (pyrido [2,3-D] pyrimidine) and basic skeleton 2 (4-methoxy-phenyl) are the basic structures for realizing mTOR inhibitory activity and thus regulating seed activity, and on this basic skeleton, 5-amino-2,6-piperidindione is derived at the 3-position of the benzene ring of basic skeleton 2, which can better realize the AZD8055 compound in enhancing seed activity.

[0025] In order to illustrate how to synthesize the basic skeleton of AZD8055 compound, the synthesis idea is explained as follows:

[0026] Based on the retrosynthetic method, the analysis is as follows:

[0027]

[0028] Therefore, the synthesis method of the basic skeleton of the AZD8055 compound shown in general formula (I) comprises the following steps:

[0029] 2,6-Dichloro-6-carboxypyridine synthesis

[0030] Will synthesis

[0031] Will Synthesis of the chemical structure of general formula (I)

[0032]

[0033] Those skilled in the art can implement specific synthesis steps through synthetic experimental means.

[0034] Subsequently, since the molecular structure of 5-amino-2,6-piperidinyldione contains an amino group and two carbonyl groups, which are the main active groups for biological activity, a AZD8055 derivative containing 5-amino-2,6-piperidinyldione was obtained:

[0035]

[0036] Effect verification:

[0037] In order to illustrate the effect of the AZD8055 derivative containing 5-amino-2,6-piperidindione of the present invention in improving seed vigor, the following experiment was conducted.

[0038] The AZD8055 compound involved in the experimental example is:

[0039] Drug name: AZD-8055

[0040] CAS No.:1009298-09-2

[0041] Molecular formula: C 25 H 31 N5O4

[0042] Molecular weight: 465.54

[0043] Chemical Structure:

[0044]

[0045] Experimental Examples The AZD8055 derivative containing 5-amino-2,6-piperidindione is:

[0046]

[0047] The AZD8055 compound and its AZD8055 derivatives containing 5-amino-2,6-piperidindione were used to treat the seeds of different crops to enhance their vitality. The details are as follows:

[0048] 1.1 Seed germination experiment: refer to Wang et al. (2010) with slight modifications. Seeds of promoted varieties such as rice, sweet corn, soybean, tomato, cucumber, water spinach, Chinese cabbage and their related stockpiles were used as test objects. Three replicates were set for each material. 50 mature and plump seeds were selected for each replicate and placed in a transparent disposable culture dish with a diameter of 9 cm covered with filter paper. 10 mL of distilled water was added, and then the culture dish was placed in a 28°C constant temperature and light incubator (light 12 h / dark 12 h) for 5 or 7 days. The germination standard was when the embryo broke through the seed coat by 2 mm, and the seedling standard was when the radicle reached the length of the seed and the embryo reached more than half of the length of the seed. The number of seeds that germinated and seedled was counted every 12 hours. The germination rate for 5 consecutive days was counted as the 5-day germination potential (GP), germination index (GI) = ∑ (Gt / Dt) (Dt represents the number of germination days), Gt represents the number of germinated seeds per day corresponding to Dt, and T50 is the time required for the germination rate to reach half (d: day).

[0049] 1.2 Germination experiment with exogenous reagents: For different crops, select the corresponding concentration of reagents from 0μM, 0.2μM, 2μM, 5μM, and 10μM for exogenous treatment. The germination rate of 3-5 days under different concentration conditions and the germination potential for 5 consecutive days are statistically analyzed.

[0050] 1.3 Seedling growth identification experiment:

[0051] (1) Select 50 mature and plump seeds and gently peel off the husks, trying to avoid damaging the embryo.

[0052] (2) Place the shelled seeds in a 50°C oven for about 3 days to break dormancy.

[0053] (3) Then pour the seeds into a 50 mL sterile centrifuge tube, add 10 mL of 75% anhydrous ethanol, and wash the seeds on a shaker at 200 rpm for 5 min. Pour off the alcohol in a clean bench (be careful not to drop the seeds), and wash once with sterile water.

[0054] (4) Add 5 mL of 2.5% sodium hypochlorite in a clean bench and wash the seeds on a shaker at 200 rpm for 15-20 min. Then pour out the sodium hypochlorite in the clean bench and wash with sterile water for 3-5 times.

[0055] (5) Place the washed seeds on sterile filter paper in a clean bench to absorb moisture. Use tweezers that have been sterilized by burning to carefully pick up the dried seeds and place them on a 1 / 2MS culture medium plate. After inoculation, seal the culture dish with sealing film and place it in a 28°C incubator in the dark for 2 days.

[0056] (6) After most of the seeds have turned white, they are disinfected with alcohol on the surface and opened in a clean bench. Seeds with consistent germination are inoculated onto 1 / 2MS culture medium plates containing reagents of different concentrations. After sealing, they are placed in a 28°C constant temperature and light incubator (12 h light / 12 h dark) for 12 days.

[0057] (7) Count the length of rice seedlings, root length and number of roots, and record and take photos.

[0058] 1.4 Seedling soil culture growth experiment:

[0059] Three replicates were set for each material. Thirty mature and plump seeds were selected for each replicate and placed in a 9-cm diameter transparent disposable culture dish covered with filter paper. 10 mL of distilled water or reagent treatment solution was added, and then the culture dish was placed in a 28°C constant temperature and light incubator (12 h of light / 12 h of darkness) for 3 days. The seeds were then transferred to a pot filled with moist field soil and placed in a 28°C constant temperature and light incubator (12 h of light / 12 h of darkness) for 14 days. During this period, the growth of the seedlings was observed and recorded and photographed.

[0060] Experimental Example 1

[0061] The japonica rice variety Zhonghua 11 and the indica rice varieties Nayou 51 and Shengyou 6126 were tested. The results showed that compared with the AZD8055 treatment, Figure 1 The results showed that the AZD8055 derivative containing 5-amino-2,6-piperidindione (labeled as YSW-5) had a higher effect of improving seed germination rate, and the application of 5-amino-2,6-piperidindione in improving seed activity was developed.

[0062] Experimental Example 2

[0063] Maize varieties were also tested, and compared with the AZD8055 treatment, Figure 2 The results showed that the AZD8055 derivatives containing 5-amino-2,6-piperidinyldione were found to have an improved effect on germination rate compared with AZD8055 treatment. At the same time, in the test of direct seeding soil after treatment, these derivatives had a better effect on improving seedling establishment rate, further demonstrating that the AZD8055 derivatives of 5-amino-2,6-piperidinyldione have a higher effect on improving seed germination rate, and developed the application of 5-amino-2,6-piperidinyldione in improving seed activity.

[0064] Experimental Example 3

[0065] The test was also conducted on sweet corn varieties stored for 1 year. Figure 3 The results showed that the AZD8055 derivative containing 5-amino-2,6-piperidinedione had a good effect on improving the germination rate and seedling rate, which further demonstrated that the AZD8055 derivative containing 5-amino-2,6-piperidinedione had a higher effect on improving the seed germination rate and developed the application of 5-amino-2,6-piperidinedione in improving seed activity.

[0066] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. An AZD8055 derivative containing 5-amino-2,6-piperidindione, characterized in that: It is a chemical structure shown in general formula (I):

2. Use of the AZD8055 derivative containing 5-amino-2,6-piperidindione as claimed in claim 1 in improving the vitality of crop seeds.

3. The use according to claim 2, characterized in that: The seeds are crop seeds.

4. The use according to claim 3, characterized in that: The crop seeds include rice, sweet corn, soybean, tomato, cucumber, water spinach and Chinese cabbage.

5. The use according to claim 2, characterized in that: The crop seeds are rice and corn.

6. Use of the AZD8055 derivative containing 5-amino-2,6-piperidindione as claimed in claim 1 in the preparation of a drug for improving the vitality of crop seeds.

7. The drug according to claim 6, characterized in that The drug is administered in the following manner: the drug is mixed with seeds, and the seeds are allowed to germinate and grow.

8. The drug according to claim 6, characterized in that The concentration of the AZD8055 derivative containing 5-amino-2,6-piperidindione in the drug was 2 μM.

9. A pharmaceutical composition, characterized in that The invention contains the AZD8055 derivative containing 5-amino-2,6-piperidindione as claimed in claim 1 as an active ingredient and one or more pharmaceutical excipients.

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