欢迎登录材料期刊网

材料期刊网

高级检索

芳基异硫氰酸酯是一类应用极为广泛的有机中间体和重要试剂,用于合成多种含氮、含硫、或含氧等杂环化合物,广泛应用于农药、医药和精细化工等领域.其合成方法及应用受到化学家的广泛重视.文章综述了芳基异硫氰酸酯的多种合成方法及其在化合物合成、医药方面的应用.

参考文献

[1] Takashi Otani;Shinichi Kunimatsu;Taku Takahashi .TfOH-promoted transformation from 2-alkynylphenyl isothiocyanates to quinoline-2-thiones or indoles[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2009(27):3853-3856.
[2] Jing-Wen Qiu;Xing-Guo Zhang;Ri-Yuan Tang .Iron-Catalyzed Tandem Reactions of 2-Halobenzenamines with Isothiocyanates Leading to 2-Aminobenzothiazoles[J].Advanced synthesis & catalysis,2009(14/15):2319-2323.
[3] 高中良,刘秀莲,刘东,张丽英.异硫氰酸酯的合成[J].农药,2009(05):322-325,334.
[4] 李泽友,沈文涛,周鹏.异硫氰酸苄酯的防癌抗癌作用与生物合成研究进展[J].医学综述,2009(17):2598-2599.
[5] Gong, Aiyu;He, Meilan;Krishna Vanaja, Donkena;Yin, Ping;Karnes, R. Jeffrey;Young, Charles Y.F. .Phenethyl isothiocyanate inhibits STAT3 activation in prostate cancer cells[J].Molecular Nutrition and Food Research,2009(7):878-886.
[6] 刘涛,刘强.2-氟-4-氯-5-甲氧羰基甲硫基苯基异硫氰酸酯合成工艺的研究[J].当代化工,2013(05):669-672.
[7] 袁露,钟宏,刘广义.异硫氰酸酯的制备及应用[J].精细化工中间体,2007(06):10-13,25.
[8] 曹瑞雲 .芳香族异硫氰酸酯与有机卤化锌试剂的反应研究[D].西北师范大学,2011.
[9] Stanley R S;Wolf K.Organic functional group preparations,second edition[M].New York:Academic Press,Inc,1986:359-360.
[10] Goddard;Steven J .Novel 2-aryl-2,3,5,6,7,8-hexahydro-3-thioxoimidazo-[1,5-α-]pyridine-1 (BaH)-ores as herbicides[P].US,4138242,1979-02-06.
[11] 王晓乐,孙烈,江才鑫.苯基异硫氰酸酯的合成方法[J].浙江化工,2006(10):11-13.
[12] Ogata M;Watanabe Tawara K .Phenyl isothiocyanate derivatives and their production[P].US,4248869,1981-02-03.
[13] 杨旭,金淑惠,杨彩霞,王道全.2-(1,5-亚戊基)-5-取代亚氨基-Δ3-1,3,4-噻二唑啉的合成及杀菌活性[J].农药学学报,2004(01):22-25.
[14] 黄润秋;王惠林;周嘉.有机中间体制备[M].北京:化学工业出版社,1997:54-58.
[15] Rince Wong;Sarah J. Dolman .Isothiocyanates from Tosyl Chloride Mediated Decomposition of in Situ Generated Dithiocarbamic Acid Salts[J].The Journal of Organic Chemistry,2007(10):3969-3971.
[16] 陈美航 .含膦酸酯的手性硫脲化合物的合成和生物活性研究[D].贵州大学,2009.
[17] Cyrille Sabot;Michel Mosser;Cyril Antheaume;Charles Mioskowski;Rachid Baati;Alain Wagner .Novel chiral derivatizing isothiocyanate-based agent for the enantiomeric excess determination of amines[J].Chemical communications,2009(23):3410-3412.
[18] 何谋海,钟宏,张宝元.异硫氰酸酯及其衍生物的制备和应用进展[J].精细与专用化学品,2010(07):9-13.
[19] 杜晓华,许响生,傅幼锋,楼泳淋,徐振元.非硫光气法合成一些难合成的芳基异硫氰酸酯[J].农药,2004(02):78-79.
[20] 蒋胜前,王周玉,蒋珍菊,陈万义,李建惠.不活泼芳胺异硫氰酸酯的合成研究[J].四川师范大学学报(自然科学版),2011(03):388-391.
[21] 方永勤;武安邦 .2,6-二异丙基-4-苯氧基芳基异硫氰酸酯的合成[J].常州大学学报(自然科学版),2012,24(4):24-27.
[22] Rasschaert A T;Benoy G J .Method for the preparation of arylisothiocyanates[P].GB,1099768,1968-01-17.
[23] 杨锦宗.工业有机合成基础[M].北京:中国石化出版社,1997:526.
[24] 彭锋;邱晓敏;冯颂延 .合成3,4-二氟芳基异硫氰酸酯的绿色工艺[J].中南药学,2009(7):7-8.
[25] 陈伟荣,SUN Nan,MO Wei-min.异硫氰酸酯的合成方法及应用[J].浙江化工,2009(12):21-25.
[26] Harashadas M M;Srinivas D;Yadav J S .AGeneral Synthesis of Isothiocyanates from Dithiocarbamates Using Ciaycop[J].Tetrahedron Letters,1997,38(50):8743-8744.
[27] L. Valette;S. Poulain;X. Fernandez;L. Lizzani-Cuvelier .Efficient and solvent-free microwave-accelerated synthesis of isothiocyanates using Lawesson’s reagent[J].Journal of sulfur chemistry,2005(2):155-161.
[28] 王帅,钟宏,吴浩,张戈.对苯二甲酰基二异硫氰酸酯的合成工艺研究[J].精细化工中间体,2005(05):21-23.
[29] Sommen G.Phenyl isothioeyanate:a very useful reagent in heteroeyelie synthesis[J].SYNLETT,2004(7):1323-1324.
[30] Mei-Hang Chen;Zhuo Chen;Bao-An Song .Synthesis and Antiviral Activities of Chiral Thiourea Derivatives Containing an α-Aminophosphonate Moiety[J].Journal of Agricultural and Food Chemistry,2009(4):1383-1388.
[31] Jing-Zi Liu;Bao-An Song;Hui-Tao Fan .Synthesis and in vitro study of pseudo-peptide thioureas containing α-aminophos-phonate moiety as potential antitumor agents[J].European Joumal of Medicinal Chemistry,2010,45(11):5108-5112.
[32] Jing-Zi Liu;Song Yang;Xiang-yang Li et al.Synthesis and Antiviral Bioactivity of Chiral Thioureas Containing Leucine and Phosphonate Moieties[J].MOLECULES,2010,15(8):5112-5123.
[33] 刘静姿;胡俊锋;史大斌.手性膦酸酯硫脲的抗TMV活性及作用机制研究[J].西南师范大学学报(自然科学版),2014(11)
[34] Liu, J.-Z.;Song, B.-A.;Bhadury, P.S.;Hu, D.-Y.;Yang, S. .Synthesis and bioactivities of α-aminophosphonate derivatives containing benzothiazole and thiourea moieties[J].Phosphorus, Sulfur, and Silicon and the Related Elements,2012(1/3):61-70.
[35] YANG Xuan,SONG BaoAn,JIN LinHong,WEI Xue,BHADURY S Pinaki,LI XiangYang,YANG Song,HU DeYu.Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety[J].中国科学:化学(英文版),2011(01):103-109.
[36] Yi-Ju Cao;Yuan-Yuan Lai;Xiang Wang .Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2007(26):21-24.
[37] Klausen, RS;Jacobsen, EN .Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions[J].Organic letters,2009(4):887-890.
[38] Wang, W.-H.;Abe, T.;Wang, X.-B.;Kodama, K.;Hirose, T.;Zhang, G.-Y. .Self-assembled proline-amino thioureas as efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroolefins[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2010(24):2925-2933.
[39] Hai-Feng Cui;Peng Li;Xiao-Wei Wang.Asymmetric Michael addition of α-fluoro-α-phenylsulfonyl ketones to nitroolefins catalyzed by phenylalanine-based bifunctional thioureas[J].Journal of Fluorine Chemistry,2012:120-126.
[40] 仓顺东 .异硫氰酸苯乙酯与紫杉醇协同抗乳腺癌细胞的作用及其机制的研究[D].郑州大学,2010.
[41] Miran Jang;Eunyoung Hong;Gun-Hee Kim .Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables.[J].Journal of Food Science,2010(7):M412-M416.
[42] 袁鹏,陈宝安,刘德龙.异硫氰酸盐的抗肿瘤机制和研究进展[J].中国天然药物,2008(05):325-332.
[43] 陈楠,任凌燕,戴传云.两种异硫氰酸酯抗肿瘤的研究进展[J].食品与机械,2012(02):241-244.
[44] 王龙贵;乔仁伟;程景才 .一种天然及人工合成的异硫氰酸酯类化合物及其在治疗和预防癌症中的应用[P].CN,1724516A,2006-01-05.
[45] Satyan K S;Swanmy N;Dizon D S .Phenethyl isothiocyanate(PITC)inhibits growth of ovarian cancer cells by inducing apoptosis:Role of caspase and MAPK activiation[J].Gynecologic Oncology,2006,103(1):261-270.
[46] 蔡圣宝 .壳寡糖及其新型衍生物的制备和抗肿瘤活性初步研究[D].中国科学院海洋研究所,2009.
[47] Jan, C.-R.;Chen, C.-Y.;Wang, S.-C.;Kuo, S.-Y. .Phenethyl isothiocyanate induces Ca~(2+) movement and cytotoxicity in PC3 human prostate cancer cells[J].Journal of the Taiwan Institute of Chemical Engineers,2011(6):895-901.
[48] 高宁 .异硫氰酸酯类化合物在制备治疗白血病的药物中的应用[P].CN,101474170A,2009-07-08.
[49] Pramod K;Dash;Houeton .Methods and compostitions for treatment of central nervous system injury with isothiocyanates[P].US,0116423 A1,2006-01-01.
[50] Parul Gupta;Sanjay K Srivastava .Antitumor activity of phenethyl isothiocyanate in HER2-positive breast cancer models[J].BMC Medicine,2012,10:80-98.
上一张 下一张
上一张 下一张
计量
  • 下载量()
  • 访问量()
文章评分
  • 您的评分:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%