Design,synthesis, and toward a side-ring optimization of tricyclic thieno[2,3-d]pyrimidin-4(3H)-ones and their effect on melanin synthesis in murine B16 cells |
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| Authors: | Li Fei Nie Khurshed Bozorov Guozheng Huang Jiangyu Zhao Chao Niu |
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| Institution: | 1. Key Laboratory of Plant Resources and Chemistry in Arid Regions, State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, P. R. China;2. University of Chinese Academy of Sciences, Beijing, P. R. China;3. Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, Uzbekistan |
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| Abstract: | AbstractHerein, we report the synthesis of 48 novel 3-sulfonylamides containing a tricyclic thieno2,3-d]pyrimidin-4(3H)-one moiety, and their influence on melanin synthesis in murine B16 cells. All target sulfonylamides were synthesized through key intermediate 3-nitro-thieno2,3-d]pyrimidin-4(3H)-ones using three types of ipso-nitration reactions. In this case, we converted the pyrido1,2-a]- fragment of the thieno2,3-d]pyrimidine moiety to pyrrolo1,2-a]- and azepino1,2-a]- side-rings in order to evaluate the bioactivities of the synthesized derivatives for a structure activity-relationships point of view. The obtained results suggest that some of the selected compounds revealed a promising influence on melanin synthesis in murine B16 cells and may serve as lead compounds for further drug discovery and development. |
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| Keywords: | Thieno[2 3-d]pyrimidin-4(3H)-ones sulfonylamides ipso-nitration melanin synthesis murine B16 cells |
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