新型取代吲哚-3-甲醇类衍生物的合成
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摘要
以取代吲哚为原料,经维尔斯迈尔-哈克反应制得取代吲哚-3-甲醛,再通过DMSO/NaOH体系制得N-取代吲哚-3-甲醛(3a~3g);3a~3g经Na BH4还原合成了7个未见文献报道的取代吲哚-3-甲醇类衍生物(4a~4g),其结构经~1H NMR,~(13)C NMR和MS表征。
N-substituted indole-3-formaldehydes(3a~3g) were synthesized in the system of dimethyl sulfoxide and sodium hydroxide by reation of substituted indole-3-formaldehydes,which were obtained by Vilsmeier-Haack reaction of substituted indoles.Seven novel substituted indole-3-methanols were synthesized by reduction of 3a~3g with sodium borohydride as the reagent.The structures were characterizd by ~1H NMR,~(13)C NMR and MS.
N-substituted indole-3-formaldehydes(3a~3g) were synthesized in the system of dimethyl sulfoxide and sodium hydroxide by reation of substituted indole-3-formaldehydes,which were obtained by Vilsmeier-Haack reaction of substituted indoles.Seven novel substituted indole-3-methanols were synthesized by reduction of 3a~3g with sodium borohydride as the reagent.The structures were characterizd by ~1H NMR,~(13)C NMR and MS.
引文
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[15]Coowar D,Bouissac J,Hanbali M,et al.Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres[J].Journal of medicinal chemistry,2004,47(25):6270-6282.
[16]Dubey P K,Babu B,Narayana M V.Synthesis of Nalkyl/aralkyl derivatives of indole-3-aldehydes using TEBAC as phase transfer catalyst[J].Indian Journal of Heterocyclic Chemistry,2006,15(3):205-208.
[2]司伟杰,张涛,张开心,等.新型苯并咪唑衍生物的合成及其生物活性[J].合成化学,2016,24(5):369-373.
[3]王亮,顾昌翰,瞿星,等.5,6-二甲氧基吲哚的合成[J].化学研究与应用,2016,28(2):247-250.
[4]Belton M,Commerford K,Hall J,et al.Catalytic functionalization of indoles in a new dimension[J].Angewandte Chemie,2009,48(51):9608-9644.
[5]陶炳志,陈河如.抗肿瘤化合物6-溴代吲哚-3-甲醇的设计合成[J].中山大学学报:自然科学版,2012,51(2):63-65.
[6]Wattenberg L W,Loub W D.Inhabition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles[J].Cancer Research,1978,38(5):1410-1413.
[7]Staub R E,Feng C,Onisko B,et al.Fate of indole-3-carbinol in cultured human breast tumor cells[J].Chemical Research in toxicology,2002,15(2):101-109.
[8]于良民,王利,李霞,等.二吲哚基甲烷及其衍生物的合成与表征[J].精细化工,2006,23(5):483-486.
[9]周佳栋,曹飞,李振江,等.N-取代吲哚-3-甲醇的合成[J].精细化工,2007,24(4):380-384.
[10]Riby J E,Feng C,Chang Y C,et al.The major cyclic trimeric product of indole-3-carbinol is a strong agonist of the estrogen receptor signaling pathway[J].Biochemistry,2000,39(5):910-918.
[11]叶洋,周建伟,陆荣柱.天然产物3,3'-二吲哚甲烷的抗肿瘤作用及其机制研究概况[J].卫生研究,2014,(6):1043-1047.
[12]孙超,贾玉萍,袁栋栋.吲哚-3-甲醇抗肿瘤作用机制的研究进展[J].海峡药学,2015,27(7):10-13.
[13]罗丽娜,余龙江,郭鸣,等.3-吲哚甲醇的抗肿瘤作用[J].华西药学杂志,2008,23(1):44-47.
[14]葛裕华,吴亚明,薛忠俊.取代吲哚-3-甲醛类化合物的合成[J].有机化学,2006,26(4):563-567.
[15]Coowar D,Bouissac J,Hanbali M,et al.Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres[J].Journal of medicinal chemistry,2004,47(25):6270-6282.
[16]Dubey P K,Babu B,Narayana M V.Synthesis of Nalkyl/aralkyl derivatives of indole-3-aldehydes using TEBAC as phase transfer catalyst[J].Indian Journal of Heterocyclic Chemistry,2006,15(3):205-208.