AZD8055 Derivatives Based on N-Methyl-2-hydroxyethylamine and Their Uses

Abstract

This invention relates to the field of crop seed vigor regulation technology, specifically to the AZD8055 derivative based on N-methyl-2-hydroxyethylamine and its uses. The AZD8055 derivative based on N-methyl-2-hydroxyethylamine has the chemical structure shown in general formula (I). This AZD8055 derivative can greatly enhance seed vigor and increase crop yield per acre, making it suitable for large-scale production and application.

Description

Technical Field

[0001] This invention relates to the field of crop seed vigor regulation technology, specifically to the AZD8055 derivative of N-methyl-2-hydroxyethylamine and its uses. Background Technology

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

[0003] When environmental conditions become suitable, seeds undergo a series of physiological and biochemical changes to 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 crucial role in seed dormancy and germination. The main hormone is abscisic acid (ABA). ABA usually promotes seed dormancy, while ABA accumulation inhibits seed germination. Regulating seed dormancy is of great significance for agricultural production, seed storage, and plant resource conservation. Therefore, developing products suitable for improving seed vigor can reduce quality and yield losses caused by seed germination, ensuring increased and stable crop yields and food security. Summary of the Invention

[0004] The purpose of this invention is to overcome the shortcomings of the prior art by providing an AZD8055 derivative of N-methyl-2-hydroxyethylamine and its uses. This AZD8055 derivative can efficiently enhance seed vigor, promote rapid seed germination, and effectively reduce the quality and yield losses caused by seed spike germination.

[0005] To achieve the above objectives, the present invention provides the following technical solution:

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

[0007]

[0008]

[0009] The use of the above-mentioned N-methyl-2-hydroxyethylamine AZD8055 derivative in improving crop seed vigor is provided.

[0010] In some embodiments, the seed is a crop seed.

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

[0012] In some embodiments, the corn is a seed that has been stored for more than one year.

[0013] The above-mentioned N-methyl-2-hydroxyethylamine AZD8055 derivative is provided for use in the preparation of a drug to improve crop seed vigor.

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

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

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

[0017] This invention, through research, has discovered that the AZD8055 derivative based on N-methyl-2-hydroxyethylamine can significantly enhance crop seed vigor. The pyrido[2,3-D]pyrimidine and 4-methoxy-phenyl groups in the AZD8055 derivative skeleton can regulate the ABA (abscisic acid) signaling pathway, thereby effectively enhancing crop seed vigor and promoting rapid seed germination and robust, uniform seedling emergence. N-methyl-2-hydroxyethylamine can further enhance crop seed vigor in coordination with its skeleton. This invention develops applications of N-methyl-2-hydroxyethylamine in improving seed vigor, suitable for large-scale production and application. Attached Figure Description

[0018] Figure 1 This is the detection of the effect of the N-methyl-2-hydroxyethylamine-based AZD8055 derivative on improving the germination rate of different rice varieties in Experiment Example 1.

[0019] Figure 2 This is an example of the effect of the N-methyl-2-hydroxyethylamine-based AZD8055 derivative on the germination rate and seedling rate of maize seeds stored for one year, as tested in Experiment 2.

[0020] Figure 3 This is a schematic diagram of the basic skeleton of the AZD8055 compound. Detailed Implementation

[0021] Preferred embodiments of the invention will now be described in more detail with reference to the accompanying drawings. While preferred embodiments of the invention are shown in the drawings, it should be understood that the invention can be implemented in various forms and should not be limited to the embodiments set forth herein. Rather, these embodiments are provided so that the invention will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

[0022] Example 1

[0023] To illustrate the method for obtaining the AZD8055 derivative of N-methyl-2-hydroxyethylamine of the present invention, the following is disclosed:

[0024] like Figure 3 The basic skeleton of the AZD8055 compound shown is shown in the figure. The basic skeleton 1 (pyrido[2,3-D]pyrimidine) and the basic skeleton 2 (4-methoxy-phenyl) are the basic structures for regulating seed vigor by achieving mTOR inhibition activity. On this basic skeleton, the 3-position derivative of N-methyl-2-hydroxyethylamine on the benzene ring of the basic skeleton 2 can better realize the effect of the AZD8055 compound in improving seed vigor.

[0025] To illustrate how the basic framework of the AZD8055 compound was synthesized, the synthetic approach is explained below:

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

[0027]

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

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

[0030] Will synthesis

[0031] Will Chemical structure of general formula (I)

[0032]

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

[0034] Subsequently, regarding R 1 The design was carried out to obtain AZD8055 derivatives based on N-methyl-2-hydroxyethylamine:

[0035]

[0036] Effect verification:

[0037] To demonstrate the effect of the N-methyl-2-hydroxyethylamine derivative AZD8055 of the present invention on improving seed vigor, the following experiments were conducted.

[0038] The AZD8055 compound involved in the experimental examples 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] The experimental example of the AZD8055 derivative of N-methyl-2-hydroxyethylamine is:

[0046]

[0047] Seed vigor enhancement treatments for different crops were carried out using AZD8055 compound and its AZD8055 derivative, N-methyl-2-hydroxyethylamine, as detailed below:

[0048] 1.1 Seed germination experiment: The method was slightly modified from Wang et al. (2010). Seeds of popular varieties of rice, sweet corn, soybean, tomato, cucumber, water spinach, and Chinese cabbage, along with their remaining stock, were used as the test subjects. Three replicates were set up for each material. For each replicate, 50 mature and plump seeds were selected and placed in 9cm diameter transparent disposable petri dishes lined with filter paper. 10mL of distilled water was added, and the petri dishes were then placed in a 28℃ constant temperature and light incubator (12h light / 12h darkness) for 5 or 7 days. Germination was defined as the embryo breaking through the seed coat by 2mm, and seedling establishment was defined as the radicle reaching the length of the seed and the embryo reaching more than half the length of the seed. The number of germinated and established seeds was counted every 12 hours. The germination rate over 5 consecutive days is taken as the germination potential (GP) over 5 days. Germination index (GI) = ∑(Gt / Dt) (Dt represents the number of germination days), Gt represents the number of seeds germinated each day corresponding to Dt, and T50 is the time (d: days) required for the germination rate to reach half.

[0049] 1.2 Germination Experiment with Exogenous Reagent Treatment: For different crops, appropriate concentrations of reagents (0 μM, 0.2 μM, 2 μM, 5 μM, and 10 μM) were selected for exogenous treatment. The germination rate was recorded 3-5 days after application under different concentrations, and the germination potential was recorded for 5 consecutive days.

[0050] 1.3 Seedling growth assessment experiment:

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

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

[0053] (3) Then pour the seeds into a 50mL sterile centrifuge tube, add 10mL of 75% anhydrous ethanol, wash the seeds with a shaker at 200rpm for 5min, pour out the ethanol 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 to the laminar flow hood and wash the seeds with a shaker at 200 rpm for 15-20 min. Then discard the sodium hypochlorite in the laminar flow hood and wash with sterile water 3-5 times.

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

[0056] (6) After most of the seeds show white sprouts, disinfect the surface with alcohol and open it in a clean bench. Inoculate the seeds with consistent germination onto 1 / 2MS medium plates containing different concentrations of reagents. After sealing, place them in a 28℃ constant temperature light incubator (12h light / 12h dark) for 12 days.

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

[0058] 1.4 Seedling growth experiment in soil cultivation:

[0059] Each material was prepared in triplicate. For each replicate, 30 mature, plump seeds were selected and placed in 9cm diameter transparent disposable petri dishes lined with filter paper. 10mL of distilled water or reagent treatment solution was added, and the dishes were then placed in a 28℃ constant temperature and light incubator (12h light / 12h dark) for 3 days. Subsequently, the seeds were transferred to pots filled with moist field soil and placed in a 28℃ constant temperature and light incubator (12h light / 12h dark) for 14 days. Seedling growth was observed and photographed during this period.

[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 on improving seed germination rate, indicating that the application of N-methyl-2-hydroxyethylamine in improving seed vigor has been developed.

[0062] Experiment Example 2

[0063] Tests were also conducted on sweet corn varieties stored for one year. Compared to the AZD8055 treatment, Figure 2 The results showed that the AZD8055 derivative of N-methyl-2-hydroxyethylamine had a good effect on improving both germination rate and seedling rate, further demonstrating that the AZD8055 derivative of N-methyl-2-hydroxyethylamine has a higher effect on improving seed germination rate, and the application of N-methyl-2-hydroxyethylamine in improving the vigor of stored seeds has been developed.

[0064] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. Use of an N-methyl-2-hydroxyethylamine-based AZD8055 derivative in improving the vigor of crop seeds; the chemical structural formula (I) of the N-methyl-2-hydroxyethylamine-based AZD8055 derivative is: ； the crop seeds are rice, corn.

2. Use according to claim 1, characterized in that, the corn is a seed stored for more than 1 year.

3. Use of an N-methyl-2-hydroxyethylamine-based AZD8055 derivative in preparing a medicine for improving the vigor of crop seeds; the chemical structural formula (I) of the N-methyl-2-hydroxyethylamine-based AZD8055 derivative is: ； the crop seeds are rice, corn.

4. Use of an N-methyl-2-hydroxyethylamine-based AZD8055 derivative according to claim 3 for the manufacture of a medicament for increasing the viability of crop seeds, characterized in that, the administration mode of the medicine is: mixing the medicine with seeds, and making the seeds germinate and grow.

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