AZD8055 derivative based on N-methyl-2-hydroxyethylamine and application of AZD8055 derivative

Abstract

The invention relates to the technical field of regulation and control of crop seed vigor, in particular to an N-methyl-2-hydroxyethylamine-based AZD8055 derivative and application thereof.The N-methyl-2-hydroxyethylamine-based AZD8055 derivative is of a chemical structure as shown in a general formula (I): # imgabs0 #, and the AZD8055 derivative can greatly improve the seed vigor and increase the crop yield per mu and is suitable for large-scale production and application.

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 of N-methyl-2-hydroxyethylamine and a use thereof. Background Art

[0002] During the maturation process, seeds enter a dormant state due to external environmental factors or their own genetic characteristics. For example, under drought or low temperature conditions, the seeds of some plants will enter a dormant state to resist adverse environments.

[0003] When environmental conditions become suitable, seeds undergo a series of physiological and biochemical changes, break dormancy and enter the germination stage. Common methods for breaking dormancy include stratification, physical methods, chemical methods, and hormone treatment. Plant hormones play a key role in seed dormancy and germination. The main hormones include abscisic acid (ABA). ABA usually promotes seed dormancy, and the accumulation of ABA inhibits seed germination. Regulating seed dormancy is of great significance for agricultural production, seed storage, and plant resource protection. Therefore, the development of products suitable for improving seed vitality can reduce the quality and yield losses caused by seed spike germination, and ensure the increase and stability of crop yields and food safety. Summary of the invention

[0004] The purpose of the present invention is to avoid the shortcomings of the prior art and provide an AZD8055 derivative of N-methyl-2-hydroxyethylamine and its use, wherein the AZD8055 derivative can effectively enhance seed vitality, promote rapid seed germination, and effectively reduce the quality and yield losses caused by seed ear germination.

[0005] To achieve the above object, the present invention provides the following technical solutions:

[0006] Provided is an AZD8055 derivative based on N-methyl-2-hydroxyethylamine, which has a chemical structure shown in general formula (I):

[0007] .

[0009] Provided is the use of the AZD8055 derivative of N-methyl-2-hydroxyethylamine in improving the vitality of crop seeds.

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

[0011] In some embodiments, the crop seeds are rice or corn.

[0012] In some embodiments, the corn is a seed stored for more than 1 year.

[0013] Provided is the use of the above-mentioned AZD8055 derivative of N-methyl-2-hydroxyethylamine in preparing a drug for improving the vitality of crop seeds.

[0014] In some embodiments, the drug is administered by mixing the drug with seeds and allowing the seeds to germinate and grow.

[0015] There is provided a pharmaceutical composition comprising as an active ingredient the above-mentioned AZD8055 derivative of N-methyl-2-hydroxyethylamine and one or more pharmaceutically acceptable excipients.

[0016] The beneficial effects of the AZD8055 derivative of N-methyl-2-hydroxyethylamine and its use are as follows:

[0017] Through research, the present invention has found that the AZD8055 derivative based on N-methyl-2-hydroxyethylamine can improve the vitality of crop seeds more excellently. The pyrido [2,3-D] pyrimidine and 4-methoxy-phenyl in the skeleton of the AZD8055 derivative of N-methyl-2-hydroxyethylamine can achieve the regulation of the ABA (plant hormone abscisic acid) signal pathway, which can then effectively improve the vitality of crop seeds and promote rapid germination of seeds and robust and consistent emergence. N-methyl-2-hydroxyethylamine can coordinate with its skeleton to further improve the vitality of crop seeds, and the application of N-methyl-2-hydroxyethylamine in improving seed vitality has been developed, which is suitable for large-scale production and application. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 This is a test of the improvement effect of the AZD8055 derivative based on N-methyl-2-hydroxyethylamine in Experimental Example 1 on the germination rate of seeds of different rice varieties.

[0019] Figure 2 This is a test of the treatment effect of the AZD8055 derivative based on N-methyl-2-hydroxyethylamine in Experimental Example 2 on the germination rate and seedling rate of corn seeds stored for one year.

[0020] Figure 3 It is a schematic diagram of the basic skeleton of the AZD8055 compound. 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 acquisition method of the AZD8055 derivative of N-methyl-2-hydroxyethylamine of the present invention, the following contents are disclosed:

[0024] like Figure 3 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 achieving mTOR inhibition activity and thus regulating seed activity, and on this basic skeleton, N-methyl-2-hydroxyethylamine is derived at the 3-position of the benzene ring of basic skeleton 2, which can better achieve the effect of 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] Then, R 1 Designed to specifically obtain AZD8055 derivatives based on N-methyl-2-hydroxyethylamine:

[0035]

[0036] Effect verification:

[0037] In order to illustrate the effect of the AZD8055 derivative of N-methyl-2-hydroxyethylamine 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 N 5 O 4

[0042] Molecular weight: 465.54

[0043] Chemical Structure:

[0044]

[0045] Experimental Example The AZD8055 derivative of N-methyl-2-hydroxyethylamine is:

[0046]

[0047] The AZD8055 compound and its AZD8055 derivative of N-methyl-2-hydroxyethylamine were used to improve the vitality of seeds of different crops. 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 root number, 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 of N-methyl-2-hydroxyethylamine (labeled as YSW-6) had a higher effect of improving the seed germination rate. It can be seen that the application of N-methyl-2-hydroxyethylamine in improving seed vitality has been developed.

[0062] Experimental Example 2

[0063] The test was also conducted on sweet corn varieties stored for 1 year. Figure 2 The results showed that the AZD8055 derivative of N-methyl-2-hydroxyethylamine had a good effect on improving the germination rate and seedling rate, which further demonstrated that the AZD8055 derivative of N-methyl-2-hydroxyethylamine had a higher effect on improving the seed germination rate, and developed the application of N-methyl-2-hydroxyethylamine in improving the vitality of stored seeds.

[0064] 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 based on N-methyl-2-hydroxyethylamine, characterized in that It is a chemical structure shown in general formula (I):

2. Use of the N-methyl-2-hydroxyethylamine-based AZD8055 derivative according to claim 1 in improving the vigor of crop seeds.

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

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

5. The use according to claim 2, characterized in that: The corn is seeds stored for more than one year.

6. Use of the AZD8055 derivative of N-methyl-2-hydroxyethylamine according to claim 1 in the preparation of a medicament 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. A pharmaceutical composition, characterized in that It contains the AZD8055 derivative of N-methyl-2-hydroxyethylamine as claimed in claim 1 as an active ingredient and one or more pharmaceutical excipients.

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