Citation: ZHANG Zhi-Jian, JIANG Wu-Jiu, TAN Yu-Xing, LIU Yang, ZHU Xiao-Ming, ZHANG Fu-Xing, KUANG Dai-Zhi. Syntheses,Crystal Structures and Biological Activity of the 2-Oxo-propionic Acid Aroyl Hydrazone Di-4-methylbenzyltin Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2016, 32(11): 2003-2011. doi: 10.11862/CJIC.2016.266 shu

Syntheses,Crystal Structures and Biological Activity of the 2-Oxo-propionic Acid Aroyl Hydrazone Di-4-methylbenzyltin Complexes

  • Corresponding author: ZHANG Zhi-Jian, 
  • Received Date: 2 July 2016
    Available Online: 7 October 2016

    Fund Project:

  • Di-4-methylbenzyltin dichloride has been synthesized via the reaction of the tin powder with the 4-methylbenzyl chloride in the hydrous toluene. Two substituted benzyltin complexes has been synthesized via the reaction of the 2-oxo-propionic acid aroyl hydrazone with the di-4-methylbenzyltin dichloride. The complexes 1 and 2 have been characterized by IR, 1H NMR, 13 NMR spectra, elemental analysis and the crystal structures have been determined by X-ray diffraction. In vitro antitumor activities of both complexes were evaluated by the 3-(4,5-dimethylthiazoly-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against three human cancer cell lines(MCF-7, HepG2, NCI-H460) and human cell line(HL-7702). Two complexes exhibited strong antitumor activity, moreover, 2 was less toxic than 1. The interaction between complexes and calf thymus DNA were studied by EB fluorescent probe. The interaction of 1 with calf thymus DNA were intercalation and electrostatic attraction, however, that of 2 was only intercalation. CCDC:1487539, 1; 1053263, 2.
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    1. [1]

      [1] Brown N M. Thesis for the Doctorate of Clemson University. 1972.

    2. [2]

      [2] Crowe A J, Smith P J, Atassi G. Chem. Biol. Interact., 1980,32(1/2):171-178

    3. [3]

      [3] Gielen M. Tin-based Antitumour Drugs. Berlin:Springer-Verlag, 1990.

    4. [4]

      [4] Shang X M, Ding N, Xiang G Y. Eur. J. Med. Chem., 2012, 48:305-312

    5. [5]

      [5] Martins M, Baptista P V, Mendo A S, et al. Mol. Biosyst., 2016,12(3):1015-1023

    6. [6]

      [6] LIAO Qi-Hua(廖启华), LIN Sen(林森), DENG Rui-Hong(邓瑞红), et al. Chin. J. Org. Chem.(有机化学), 2015,35(9): 1923-1928

    7. [7]

      [7] Hong M, Yang Y G, Li C, et al. RSC Adv., 2015,5(124): 102885-102894

    8. [8]

      [8] Sherman L R, Huber F. App. Organomet. Chem., 1988,2(1): 65-72

    9. [9]

      [9] ZHANG Fu-Xing(张复兴), KUANG Dai-Zhi(邝代治), FENG Yong-Lan(冯泳兰), et al. Chinese J. Inorg. Chem.(无机化学学报), 2014,30(10):2367-2374

    10. [10]

      [10] ZHANG Fu-Xing(张复兴), KUANG Dai-Zhi(邝代治), FENG Yong-Lan(冯泳兰), et al. Chin. J. App. Chem.(应用化学), 2014,31(3):285-289

    11. [11]

      [11] YANG Pin(杨频), GAO Fei(高飞). Principle of Biological Inorganic Chemistry(生物无机化学原理). Beijing:Science Press, 2002.

    12. [12]

      [12] Ferreira I P, Piló E D L, Recio-Despaigne A A, et al. Bioorg. Med. Chem., 2016,24(13):2988-2998

    13. [13]

      [13] Mohanraj M, Ayyannan G, Raja G, et al. J. Photochem. Photobiol. B, 2016,158:164-173

    14. [14]

      [14] Sedaghat T, Ebrahimi Y, Carlucci L, et al. J. Organomet. Chem., 2015,794:223-230

    15. [15]

      [15] HAN Jie(韩杰), ZHOU Xiao-Xia(周晓霞), CHEN Si-Bao(陈思宝), et al. Chin. J. Org. Chem.(有机化学), 2014,34(4): 741-748

    16. [16]

      [16] REN Zheng(任争), KANG Yu-Hua(康玉华), SHI Zhen-Yu (石贞玉), et al. Acta Pharm. Sin.(药学学报), 2010,45(9): 1109-1115

    17. [17]

      [17] Foscolos A S, Papanastasiou I, Foscolos G B, et al. Med. Chem. Commun., 2016,7(6):1229-1236

    18. [18]

      [18] HE Shui-Yang(何水样), CAO Wen-Kai(曹文凯), CHEN Jun-Li(陈军利), et al. Chem. J. Chinese Universities(高等学校化学学报), 2002,23(6):991-995

    19. [19]

      [19] Armarego W L F, Chai C L L. Purification of Laboratory Chemicals. 6th Ed. Oxford:Butterworth-Heinemann, 2009.

    20. [20]

      [20] Sisido K, Takeda Y, Kinugawa Z, et al. J. Am. Chem. Soc., 1961,83(3):538-541

    21. [21]

      [21] FENG Yong-Lan(冯泳兰), ZHENG Jian-Hua(郑建华), JIANG Wu-Jiu(蒋伍玖), et al. Chinese J. Inorg. Chem.(无机化学学报), 2014,30(12):2767-2774

    22. [22]

      [22] Sheldrick G M. SHELXTL Version 5.03, Siemens Analytical X-ray Division, Madison, Wisconsin, USA, 1994.

    23. [23]

      [23] García-López M C, Muoz-Flores B M, Chan-Navarro R, et al. J. Organomet. Chem., 2016,806:68-76

    24. [24]

      [24] Barba V, Zaragoza J, Höpfl H, et al. J. Organomet. Chem., 2011,696(10):1949-1956

    25. [25]

      [25] JIANG Wu-Jiu(蒋伍玖), YANG Nian-Fa(阳年发), KUANG Dai-Zhi(邝代治), et al. Chinese J. Struct. Chem.(结构化学), 2011,30(9):1327-1331

    26. [26]

      [26] Yang Y, Hong M, Xu L, et al. J. Organomet. Chem., 2016, 804:48-58

    27. [27]

      [27] JIANG Wu-Jiu(蒋伍玖), KUANG Dai-Zhi(邝代治), YU Jiang-Xi(庾江喜), et al. Chinese J. Inorg. Chem.(无机化学学报), 2012,28(11):2363-2368

    28. [28]

      [28] Vatsa C, Jain V K, Das T K. J. Organomet. Chem., 1990, 396(1):9-18

    29. [29]

      [29] Pretsch E, Buhlmann P, Martin B. Structure Determination of Organic Compounds:Tables of Spectral Data. 4th Ed. Berlin:Springer-Verlag Berlin and Heidelberg GmbH & Co. KGaA, 2009.

    30. [30]

      [30] Fulmer G R, Miller A J M, Sherden N H, et al. Organometallics, 2010,29(9):2176-2179

    31. [31]

      [31] Clark H C, Jain V K. J. Organomet. Chem., 1985,279(3):385-394

    32. [32]

      [32] Baba H S, Dietz C, Lutter M, et al. Organometallics, 2015, 34(23):5555-5565

    33. [33]

      [33] Wagner M, Zobel B, Dietz C, et al. Organometallics, 2015, 34(23):5602-5608

    34. [34]

      [34] Jímenez-Pérez V M, Camacho-Camacho C, Güizado-Rodríuez M, et al. J. Organomet. Chem., 2000,614-615:283-293

    35. [35]

      [35] Hong M, Yin H, Chen S, et al. J. Organomet. Chem., 2010, 695(5):653-662

    36. [36]

      [36] Effenberger K, Breyer S, Schobert R. Eur. J. Med. Chem., 2010,45(5):1947-1954

    37. [37]

      [37] Dandawate P, Khan E, Padhye S, et al. Bioorg. Med. Chem. Lett., 2012,22(9):3104-3108

    38. [38]

      [38] ZHAO Guo-Liang(赵国良), SHI Xia(施霞), ZHANG Jun-Ping(张均平), et al. Sci. China:Chem(中国科学:化学), 2010,40(10):1525-1535

    39. [39]

      [39] XU Jin-Gou(许金钩), WANG Zun-Ben(王尊本). Fluoresce-nce Analysis. 3rd Ed.(荧光分析法). Beijing:Science Press, 2006:64-70

    40. [40]

      [40] ZHANG Bing-Wei(张冰卫), LI Bo(李博), XIA Wen-Shui(夏文水), et al. Chin. Proc. Pharm. Sci.(药学进展), 2011,35(7): 296-303

    41. [41]

      [41] Yan C Q, Zhang J L, Liang T G, et al. Biomed. Pharmacother., 2015,71:119-127

    42. [42]

      [42] Yin H, Liu H, Hong M, et al. J. Organomet. Chem., 2012, 713(15):11-19

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