宋妮, 李英霞, 孙雪, 曲峰. 布洛芬糖衍生物的合成J. 药学学报, 2004, 39(2): 105-109.
引用本文: 宋妮, 李英霞, 孙雪, 曲峰. 布洛芬糖衍生物的合成J. 药学学报, 2004, 39(2): 105-109.
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SONG Ni, LI Ying-xia, SUN Xue, QU Feng. Synthesis of (±) ibuprofen sugar derivativesJ. Acta Pharmaceutica Sinica, 2004, 39(2): 105-109.
Citation: SONG Ni, LI Ying-xia, SUN Xue, QU Feng. Synthesis of (±) ibuprofen sugar derivativesJ. Acta Pharmaceutica Sinica, 2004, 39(2): 105-109.
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布洛芬糖衍生物的合成

Synthesis of (±) ibuprofen sugar derivatives

    摘要
  • 摘要: 目的为了降低布洛芬的胃肠损伤副作用,提高其抗炎活性,本文合成了若干布洛芬糖衍生物。方法 采用1,2∶3,4-二缩酮-半乳糖,1,3,4,5-四-O-乙酰基-2-去氧-2-氨基-葡萄糖,3,4,6-三-O-乙酰基-2-去氧-2-n-乙酰基-葡糖胺和2,3,6,2′,3′,4′,6′-七-O-乙酰基-乳糖胺作为糖基供体,分别与2-(对异丁基苯基)-丙酰氯1进行偶联,最后脱去糖环上的保护基得到了目标化合物6-(半乳糖基-O)-(±)布洛芬4,2-［2-去氧-2-氨基-葡糖基］-(±)布洛芬7,1-［2-去氧-2-n-乙酰基-β-D-葡糖氨基］-(－)布洛芬12a,1-［2-去氧-2-n-乙酰基-β-D-葡糖氨基］-(+)布洛芬12b和1-(β-乳糖氨基)-(±)布洛芬13。结果共合成了5个新化合物(4,7,12a,12b,13),利用1HNMR,13CNMR,HMQC,COSY,IR和MS对化合物进行了结构确证,并测定了目标化合物的抗炎活性。结论化合物12a的抗炎活性最好且优于布洛芬。

     

    Abstract: Aim(±) Ibuprofen sugar derivatives were prepared in order to decrease side-effects and increase bioavailability of (±) ibuprofen. MethodsThe synthesis of derivatives were performed using 1,2∶3,4-di-O-isopropylidene-β-D-galactopyranose, 1,3,4,5-tetra-O-acetyl-2-deoxy-2-amino-β-D-gluctopyranose, 3,4,6-tri-O-acetyl-2-deoxy-2-n-acetyl-β-D-gluctosylamine and 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-β-D-lactosylamine as glycosyl donors, respectively. Target products (4, 7, 12a, 12b, 13) were obtained after deprotection. ResultsFive compounds (4, 7, 12a, 12b, 13) were synthesized as new compounds. The structures of all objective compounds were confirmed by 1HNMR, 13CNMR, HMQC, COSY, IR and MS. ConclusionIt was found that 12a showed better anti-inflammatory activity than (±) ibuprofen.

     

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