Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 543-556.DOI: 10.6023/cjoc202107002 Previous Articles     Next Articles



曾艳a,b, 聂礼飞a, 牛超a, 阿依提拉•麦麦提江a,b, Khurshed Bozorova, 赵江瑜a, 阿吉艾克拜尔•艾萨a,b,*()   

  1. a 中国科学院新疆理化技术研究所 新疆特有药用资源利用重点实验室 乌鲁木齐 830011
    b 中国科学院大学 北京 100049
  • 收稿日期:2021-07-02 修回日期:2021-09-06 发布日期:2022-02-24
  • 通讯作者: 阿吉艾克拜尔•艾萨
  • 基金资助:

Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones

Yan Zenga,b, Lifei Niea, Chao Niua, Aytilla Mamatjana,b, Khurshed Bozorova, Jiangyu Zhaoa, Haji Akber Aisaa,b()   

  1. a State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011
    b University of Chinese Academy of Sciences, Beijing 100049
  • Received:2021-07-02 Revised:2021-09-06 Published:2022-02-24
  • Contact: Haji Akber Aisa
  • Supported by:
    West Light Foundation of Chinese Academy of Sciences(2018-XBQNXZ-B-004)

Based on the general framework of natural alkaloid deoxyvasicinone, forty dihydrooxazolo[5,4-d]pyrrolo[1,2-a]- pyrimidinone compounds were designed and synthesized through bioisosterism strategy. The novel compounds were confirmed by 1H NMR, 13C NMR and HRMS spectra. The main factors affecting the reactions of synthesis and the structure-activity relationships (SARs) were investigated. The activities of the target compounds against three cancer cell lines (MCF-7, HeLa and A549) were evaluated by methyl thiazolyl tetrazolium (MTT) in vitro. All the compounds were also evaluated for their antimicrobial activities by agar punch method. The results showed that 2-(naphthalen-1-yl)-6,7-dihydrooxazolo[5,4-d]- pyrrolo[1,2-a]pyrimidin-9(5H)-one (E12) and 2-(4-(trifluoromethoxy)phenyl)-6,7-dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidin-9(5H)-one (E39) exhibited relatively better anti-proliferative activities against HeLa and MCF-7 cancer cell lines, with the half maximal inhibitory concentration (IC50) values of (4.59±0.10), (6.89±1.26) μmol•L–1, respectively. 2-((3R,5R,7R)- Adamantan-1-yl)-6,7-dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidin-9(5H)-one (E6) and 2-(3,5-dichlorophenyl)-6,7-dihydrooxazolo[5,4-d]pyrrolo[1,2-a]pyrimidin-9(5H)-one (E28) showed good antimicrobial activity to C. albicans, E. coli and S. aureus.

Key words: oxazopyrimidinone, synthesis, bioisosterism, anticancer activity, antimicrobial activity, structure-activity relationships (SARs)