Huang Wei, Liu Ming-Zhen, Li Yan, Tan Ying, Yang Guang-Fu
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, PR China.
Bioorg Med Chem. 2007 Aug 1;15(15):5191-7. doi: 10.1016/j.bmc.2007.05.022. Epub 2007 May 13.
A series of new chromone analogues bearing heterocyclic thioether moiety and aurone analogues bearing cyclic tertiary amine moiety were designed and synthesized under microwave irradiation. The synthetic protocol was found to present many advantages, such as higher yields, shorter reaction time (10-20 min), mild condition, and readily isolation of the products. The synthesized compounds were assayed for their antitumor activity against four kinds of human solid tumor cell lines including HCCLM-7, Hep-2, MDA-MB-435S, and SW-480. Two compounds, (Z)-2-((4-benzyl-piperazin-1-yl)methylene)benzofuran-3(2H)-one 5e and (Z)-2-((4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)methylene)benzofuran-3(2H)-one 5f, were identified as the most promising candidates with the IC(50) values in the range of 4.1-13.1 microM. Further cell cycle studies revealed that compounds 5e and 5f arrest the cell cycle in G(0)/G(1) phase and displayed apoptosis-inducing effect on Hep-2 cells.
在微波辐射下设计并合成了一系列带有杂环硫醚部分的新色酮类似物和带有环状叔胺部分的噢哢类似物。发现该合成方法具有许多优点，如产率更高、反应时间更短（10 - 20分钟）、条件温和以及产物易于分离。对合成的化合物针对包括HCCLM - 7、Hep - 2、MDA - MB - 435S和SW - 480在内的四种人类实体瘤细胞系进行了抗肿瘤活性测定。两种化合物，(Z)-2-((4-苄基-哌嗪-1-基)亚甲基)苯并呋喃-3(2H)-酮5e和(Z)-2-((4-(双(4-氟苯基)甲基)哌嗪-1-基)亚甲基)苯并呋喃-3(2H)-酮5f，被确定为最有前景的候选物，其IC(50)值在4.1 - 13.1微摩尔范围内。进一步的细胞周期研究表明，化合物5e和5f使细胞周期停滞在G(0)/G(1)期，并对Hep - 2细胞显示出凋亡诱导作用。
