| 新型烷氧基嘧啶拼接3-吡咯螺环氧化吲哚类化合物的合成及其抗肿瘤活性 |
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| 引用本文： | 陈爽,肖乐,陈智勇,杨超,巩艺,余章彪,周英,刘雄利.新型烷氧基嘧啶拼接3-吡咯螺环氧化吲哚类化合物的合成及其抗肿瘤活性[J].合成化学,2017(1). |
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| 作者姓名： | 陈爽 肖乐 陈智勇 杨超 巩艺 余章彪 周英 刘雄利 |
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| 作者单位： | 1. 贵州医科大学 生物与工程学院,贵州 贵阳,550025;2. 郴州市第一中学 化学组，湖南 郴州 423000; 贵州大学 贵州省中药民族药创制工程中心，贵州 贵阳 550025;3. 贵州大学 贵州省中药民族药创制工程中心,贵州 贵阳,550025 |
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| 基金项目： | 国家自然科学基金地区基金资助项目，贵州省教学改革创新项目，贵州省制药工程专业学位研究生工作站，贵州省研究生教改课题 |
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| 摘 要： | 以取代烷氧基嘧啶3-烯键氧化吲哚衍生物为原料,与肌氨酸及多聚甲醛在甲苯中回流经1,3-偶极子3+2环加成反应,合成了8个新型烷氧基嘧啶拼接3-吡咯螺环氧化吲哚类化合物(3a~3h),产率67%~82%,d/r值6/1~20/1,其结构经~1H NMR,~(13)C NMR和HR-MS(ESI-TOF)表征。采用MTT法研究了3a~3h对人肺癌细胞(A549)、人前列腺癌细胞(PC-3)和人白血病细胞(K562)的体外抗肿瘤活性。结果表明:3d和3g对人白血病细胞K562具有明显的活性,IC50分别为24.1 mol·L~(-1)和32.4μmol·L~(-1),接近阳性对照药顺铂。
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| 关 键 词： | 肌氨酸 甲醛 烷氧基嘧啶3-烯键氧化吲哚 烷氧基嘧啶拼接3-吡咯螺环氧化吲哚 1 3-偶极环加成反应 合成 抗肿瘤活性 |
Synthesis and Antitumor Activities of Novel Pyrimidine-fused Spiropyrrolidine Oxindoles |
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| CHEN Shuang,XIAO Le,CHEN Zhi-yong,YANG Chao,GONG Yi,YU Zhang-biao,ZHOU Ying,LIU Xiong-li.Synthesis and Antitumor Activities of Novel Pyrimidine-fused Spiropyrrolidine Oxindoles[J].Chinese Journal of Synthetic Chemistry,2017(1). |
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| Authors: | CHEN Shuang XIAO Le CHEN Zhi-yong YANG Chao GONG Yi YU Zhang-biao ZHOU Ying LIU Xiong-li |
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| Abstract: | Eight novel pyrimidine-fused spiropyrrolidine oxindoles(3a~3h) were synthesized by 1,3-dipolar reaction of pyrimidine-fused 3-alkenyloxindoles with azomethine ylides ( thermally generated in situ from sarcosine and formaldehyde ) . The yields and d/r of 3 a~3 h were 67% ~82% and 6/1 ~20/1, respectively. The structures were characterized by 1H NMR, 13C NMR and HR-MS(ESI-TOF). The in vitro antitumor activities against human lung cancer cells( A549 ) , human prostate cancer cells PC-3 and human leukemia cells(K562) were demonstrated by MTT assays. The results showed that 3d and 3g exhibited certain in vitro inhibitory activities against K562 with IC50 of 24. 1 mol·L-1 and 32. 4 mol·L-1 , respectively, equipotent to the positive control of Cisplatin. |
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| Keywords: | sarcosine formaldehyde pyrimidine-fused 3-alkenyloxindole pyrimidine-fused 3-alkeny-loxindole 1 3-dipolar cycloaddition reaction synthesis antitumor activity |
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