Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2467-2475.DOI: 10.6023/cjoc202101056 Previous Articles     Next Articles



董金娇a, 朱昕悦a, 冯思冉a, 张超超a, 刘振明b, 乔晓强a,c,*(), 宋亚丽a,*()   

  1. a 河北大学药学院 河北省药物质量分析控制重点实验室 河北保定 071000
    b 北京大学天然药物及仿生药物国家重点实验室 北京 100191
    c 河北大学药物化学与分子诊断教育部重点实验室 河北保定 071000
  • 收稿日期:2021-01-31 修回日期:2021-02-20 发布日期:2021-03-04
  • 通讯作者: 乔晓强, 宋亚丽
  • 基金资助:
    河北省自然科学基金(B2018201269); 河北省高等学校科学技术研究(ZD2019060); 河北大学自然科学多学科交叉研究计划(DXK201912); 河北大学研究生创新(hbu2020ss054)

Synthesis and Antifungal Activity of 7-Phenyl-6H,7H-1,3,4-thia- diazolo[3,2-a]-thiochromeno[4,3-d]pyrimidine Compounds

Jinjiao Donga, Xinyue Zhua, Siran Fenga, Chaochao Zhanga, Zhenming Liub, Xiaoqiang Qiaoa,c(), Yali Songa()   

  1. a Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei 071000
    b State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191
    c Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding, Hebei 071000
  • Received:2021-01-31 Revised:2021-02-20 Published:2021-03-04
  • Contact: Xiaoqiang Qiao, Yali Song
  • Supported by:
    Natural Science Foundation of Hebei Province(B2018201269); Science and Technology Project of Hebei Education Department(ZD2019060); Young Talent of Hebei Province, the Natural Science Interdisciplinary Research Program of Hebei University(DXK201912); Post-Graduate Innovation Fund Project of Hebei University(hbu2020ss054)

According to the principle of active substructure splicing and bioisosterism, sixteen 7-phenyl-6H,7H-1,3,4-thiadia- zolo[3,2-a]-thiochromeno[4,3-d]pyrimidine compounds containing a fused-ring were designed and synthesized. The target compounds were confirmed by1H NMR, 13C NMR and HRMS. The preliminary antifungal activity assay showed that these compounds exhibited a good antifungal activity in vitro on superficial fungi, such as Mucor racemosus,Epidermophyton floccosum,Trichophyton rubrum and Trichophyton mentagrophytes, compound 5d was found to be very sensitive (minimum inhibitory concentration (MIC): 4 μg•mL –1) to Trichophyton rubrum. While on invasive fungi, such as Cryptococcus neoformans, Candida albicans and Aspergillus fumigatus, they exhibited lower activity than that of superficial fungi. They exhibited significant inhibition activity against five plant pathogens. MIC value of compound 5l against Aspergillusnigervan tiegh and Phytophthora infestans was 8 μg•mL –1.

Key words: 1,3,4-thiadiazolo[3,2-a]-thiochromeno[4,3-d]pyrimidine, plate method, antifungal activities