Balasubramide and its derivatives, synthesis method and application
A derivative and aspect technology, applied in the field of Balasubramide and its derivatives and synthesis, can solve the problems of long reaction route, special reaction conditions, low yield, etc., and achieve optimal reaction conditions, high yield and enantioselectivity. Effect
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Embodiment 1
[0037]The synthetic method condition research experiment of embodiment 1 Balasubramide derivatives
[0038] 1. Synthesis of optically active α,β-epoxy carboxylates
[0039] Referring to the method reported in the literature, we optimize the reaction conditions to 40% H 2 o 2 The aqueous solution is used as an oxidant, and a series of epoxidation of trans-cinnamaldehyde and its derivatives is catalyzed by a self-made chiral imine catalyst S-diphenylprolinol triethylsilyl ether. After 4 hours of reaction at room temperature, it is diluted with methanol , and then NBS and sodium carbonate were added for oxidative esterification at room temperature for 3h to obtain (2S,3R)-α,β-epoxy carboxylate with good yield and excellent ee value. By comparing the optical rotation data of the literature, the absolute configuration of the final product was determined to be 2S, 3R. The results are shown in Table 1.
[0040] The reaction route is:
[0041]
[0042] Table 1
[0043]
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Embodiment 2
[0069] The overall synthetic route of optically active (+)-balasubramide derivatives is as follows:
[0070]
[0071] Obtain (+)-balasubramide derivatives 3a~3j, R in the structural formula is shown in table 5 respectively:
[0072] table 5
[0073]
[0074]
[0075] The structures of (+)-balasubramide derivatives 3a~3j are as follows:
[0076]
[0077] Synthesis experiment of each step:
[0078] ① Synthesis of Compound 1a-1j
[0079]
[0080] Dissolve 3.9g of trans-cinnamaldehyde and its derivatives in 30ml of dichloromethane, then add 1.1g~1.3g of catalyst and 3.5~4.3ml of hydrogen peroxide solution, react at room temperature for 2h, add 30ml of methanol to dilute, and then add Na 2 CO 3 3.8~4.5g and N-bromosuccinimide 6.4~7.3g, continue to react for 3h, after the reaction, filter, the filtrate is evaporated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography.
[0081] Pale yellow liquid, 65% yie...
Embodiment 3
[0117] Embodiment 3 applied pharmacological test
[0118] The neuroprotective effect, antioxidant effect, anti-inflammatory effect of brain cells and cytotoxicity test of the test compound. The experimental results are shown in Table 6, Table 7, Table 8 and Table 9. It can be seen from Table 6, Table 7, Table 8 and Table 9 that the neuroprotective and antioxidant effects of the tested compounds are very low. It can be seen from Table 8 that, except for 3g, other compounds can significantly inhibit the inflammatory response produced by rat microglia, among which 3c has the strongest effect. At the same time, from figure 1 It can be seen that the cytotoxicity test shows that the compound of the present invention has no cytotoxicity.
[0119] Table 6 The brain protection effect of the test group compounds on the nerve damage caused by the nutritional deficiency of primary cultured rat cerebellar granule neurons
[0120]
[0121]
[0122] Note: the cell survival rate of ...
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