3'-吲哚-3-氧化吲哚作为一类重要的合成子,实现其C3-位和吲哚C2-位选择性转化具有一定的挑战性.本文以3'-吲哚-3-氧化吲哚与不同的苯基溴化物为起始原料,在金属钯和无机碱等条件的参与作用下,分别合成得到了 3-(2-溴苄基)-3-(3'-吲哚基)氧化吲哚(3a～3d,收率75％～90％)、螺[5,6-二氢苯并咔唑-11,3'-氧化吲哚](4a～4d,收率45％～60％)、螺[5H-茚并吲哚-10,3'-氧化吲哚](6a～6c,收率42％～48％)、(2-苯基-1H-吲哚-3-基)氧化吲哚(8a、8b,收率51％和69％),产物结构由1H NMR、13 C NMR、高分辨质谱和单晶X-射线衍射分析表征.对合成得到的部分化合物考察了其对肿瘤细胞的抑制活性,发现部分化合物对肿瘤细胞A549(3a,IC50=25.285 μmol/L)和 HepG2(3a,IC50=21.806 μmol/L;3d,IC50=32.732 μmol/L;4d,IC50=26.923μmol/L)具有一定的抑制作用.
Diversity Transformation of 3'-Indole-3-oxoindole with Phenylbromides and Its Inhibition Effect on A549 and HepG2 Tumor Cells
It is a challenging goal for 3'-indole-3-oxindoles that are used as a class of important syn-thon to achieve the site-selective conversion of its C3 and the C2 positions of indole unit.In the pres-ence of Palladium and inorganic base,the diverse conversion of 3'-indole-3-oxindole with different phenyl bromides afforded 3-(2-bromobenzyl)-3-(1-methyl-1H-indol-3-yl)oxindoles(3a～3d,75％～90％yields),5,6-dihydrospiro[benzo[b]carbazole-11,3'-oxindoles](4a～4d,45％～60％yields),5H-spiro[indeno[1,2-b]indole-10,3'-oxindoles](6a～6c,42％～48％yields),3-(2-phe-nyl-1 H-indol-3-yl)oxindoles(8a and 8b,51％and 69％yields),respectively.The structure of the synthetic compounds were determined via 1H NMR,13 C NMR,HR-MS and the single crystal X-ray diffraction analysis.The inhibition activity of the synthesized compounds against human tumor cells was investigated,and it was found that several compounds revealed certain inhibition effects on the tumor cells A549(3a,IC50=25.285 µmol/L)and HepG2(3a,IC50=21.806 µmol/L;3d,IC50=32.732 μmol/L;4d,IC50=26.923 μmol/L).
3'-indole-3-oxindoleC—H functionalizationcascade reactionone pot synthesisspiro-oxindole
NETL
NSTL
万方数据
