Synthetic method of novel chiral non-cycle purine nucleoside analogue
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A cyclic purine nucleoside and a synthesis method technology are applied in the field of synthesis of novel chiral acyclic purine nucleoside analogs, and can solve the problems of single structure, difficult to obtain chiral source, many reaction steps and the like
Inactive Publication Date: 2015-04-29
HENAN INST OF SCI & TECH
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The disadvantage is that the current chiral propylene oxide derivatives have a single structure, and the obtained chiral acyclic nucleosides have structural limitations
Chiral acyclic nucleosides have good biological activity, and the biological activity of acyclic nucleosides can be improved by changing the side chain. Therefore, a convenient, fast and efficient synthesis of new chiral acyclic nucleosides with potential pharmacological activity has been developed. The approach of nucleosides is based on solving the problems of many reaction steps, low yield, expensive raw materials, unavailable chiral sources, and single structure of target products in the synthesis process of such compounds. It not only has important theoretical significance, but also has a wide range of applications. Application prospect
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Embodiment 1
[0031]
[0032] Dissolve 0.1mmol of adenine and 0.05mmol of t-BuOK in 0.5mL of DMF in a reaction vessel, stir at room temperature for 2 hours, then add 0.11moL of epoxy cinnamyl alcohol, stir and react at 80°C for 12 hours, and obtain Chiral acyclic nucleoside analog, white solid, yield 90%, ee>99%. 1 H NMR (DMSO-d 6 ,400MHz)δ8.46(s,1H),8.12(s,1H),7.48(d,J=6.8,1H),7.33-7.25(M,5H),5.76(d,J=5.6Hz,1H) ,5.57(d,J=5.2Hz,1H),4.89(q,J=5.4Hz,1H),4.46-4.40(m,1H),3.33-3.28(m,1H),3.24-3.18(m,1H ) 13 CNMR (DMSO-d 6 , 100MHz) δ156.4, 152.8, 149.6, 140.5, 137.8, 129.2, 128.6, 128.1, 118.8, 72.4, 63.1, 59.4, HRMS: calcd for C 14 h 16 N 5 o 2 [M+H + ]286.1299, found 286.1293.HPLC DAICEL CHIRALCEL OJ-H, hexane / iPOH=90 / 10, λ=254nm; retention time: 43.196min(minor), 49.238min(major), 99%ee.flow rate 1.0mL / min .
Embodiment 2
[0034] The base t-BuOK in Example 1 was replaced by NaH, and other conditions remained unchanged, the yield of chiral acyclic nucleoside analogs was 88%, and the ee value was 99%.
Embodiment 3
[0036] The reaction temperature in Example 1 was changed to 110° C., and the other conditions remained unchanged, and the yield of chiral acyclic nucleoside analogs was 93%, and the ee value was 99%.
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Abstract
The invention discloses a synthetic method of a novel chiral non-cycle purine nucleoside analogue. The method has the beneficial effects that reaction steps are few, a chiral source is easily available, reaction conditions are relatively mild, and meanwhile, a side chain containing two chiral centers can be constructed; reference values are provided for synthesis and application of non-cycle nucleoside drugs, and a raw material is provided for the research of novel antiviral and anti-tumor drugs; meanwhile, an effective effect is provided for the construction of other non-cycle nucleosides and analogues of the other non-cycle nucleosides; furthermore, the method has wide industrial application prospect. The method comprises the steps of firstly carrying out Sharpless epoxidation reaction to obtain epoxy propenol compounds with relatively high Ee value and yield, and opening cycles of the chiral epoxy compounds by virtue of a purine base, so as to obtain the novel non-cycle nucleoside analogue containing two chiral centers, wherein an aryl substituent is located at a site 1' of the novel non-cycle nucleoside analogue.
Description
technical field [0001] The invention relates to the technical fields of chemistry and medicine, in particular to a method for synthesizing novel chiral acyclic purine nucleoside analogues. Background technique [0002] Nucleoside compounds are composed of bases and sugar groups. They have different degrees of similarities with natural nucleosides in structure, so they have the effect of confusing real ones in vivo, which can interfere with or directly act on the biosynthesis of proteins and nucleic acids. Many nucleoside analogs are enzyme inhibitors during viral replication, which can inhibit the activity of viral DNA polymerase and reverse transcriptase and compete with nucleotides for incorporation into viral DNA chains, thereby terminating or inhibiting the elongation and synthesis of viral DNA chains , so that the replication of the virus is inhibited to play an antiviral effect, so it is possible to obtain new antiviral drugs by modifying or transforming the structure ...
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