摘要
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^(1)H 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, IC_(50)=25.285μmol/L)和HepG2(3a, IC_(50)=21.806μmol/L;3d, IC_(50)=32.732μmol/L;4d, IC_(50)=26.923μmol/L)具有一定的抑制作用。
It is a challenging goal for 3′-indole-3-oxindoles that are used as a class of important synthon to achieve the site-selective conversion of its C3 and the C2 positions of indole unit.In the presence of Palladium and inorganic base,the diverse conversion of 3′-indole-3-oxindole with different phenyl bromides afforded 3-(2-bromobenzyl)-3-(1-methyl-^(1)H-indol-3-yl)oxindoles 3a~3d(4 examples,75%~90%yields),5,6-dihydrospiro[benzo[b]carbazole-11,3′-oxindoles]4a~4d(4 examples,45%~60%yields),5 H-spiro[indeno[1,2-b]indole-10,3′-oxindoles]6a~6c(3 examples,42%~48%yields),3-(2-phenyl-^(1)H-indol-3-yl)oxindoles 8a and 8b(2 examples,51%and 69%yields),respectively.The structure of the synthetic compounds was determined via ^(1)H 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,IC_(50)=25.285μmol/L)and HepG2(3a,IC_(50)=21.806μmol/L;3d,IC_(50)=32.732μmol/L;4d,IC_(50)=26.923μmol/L).
作者
卓宇晴
崔宝东
ZHUO Yuqing;CUI Baodong(College of Pharmacy,Zunyi Medical University,Zunyi 563003,China)
出处
《合成化学》
CAS
2024年第1期1-10,共10页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(22261056)
贵州省科技厅平台人才项目(黔科合平台人才-GCC[2022]032-1)。
