Citation: LIU Changhui, WEN Ruiming, HE Miao, YI Xianwen, YE Xiaoqin, FANG Lei. Synthesis and Antitumor Activities of Novel Thiosemicarbazone Derivatives with Ionone-Based Bischalcone[J]. Chinese Journal of Applied Chemistry, ;2017, 34(8): 899-904. doi: 10.11944/j.issn.1000-0518.2017.08.170022 shu

Synthesis and Antitumor Activities of Novel Thiosemicarbazone Derivatives with Ionone-Based Bischalcone

College of Chemistry and Environmental Engineering, Hu'nan City University, Yiyang, Hu'nan 413000, China

Corresponding author: LIU Changhui, changzi915@126.com
Received Date: 20 January 2017
Revised Date: 27 February 2017
Accepted Date: 28 April 2017

Fund Project: the Research Foundation of Education Bureau of Hu′nan Province, China No.15B043Supported by the Research Foundation of Education Bureau of Hu′nan Province, China(No.15B043), the Planned Science and Technology Project of Hu′nan Province, China(2009SK4027)the Planned Science and Technology Project of Hu′nan Province, China 2009SK4027

Figures(1)

In this work, a variety of new thiosemicarbazone derivatives were prepared by combining ionoe with chalcone and thiosemicarbazide according to the structure-activity combination principle. The ionone-based dichalcones were firstly synthesized through the condensation of ionone and substituted benzaldehydes, followed by thiosemicarbazide to obtain the target products. Their structures were confirmed by fourier transform infrared spectroscopy(FT-IR), nuclear magnetic resonance spectroscopy(¹H NMR and ¹³C NMR), elemental analysis, and mass spectrometry(MS). The in vitro antitumor activities against MCF-7(human breast cancer), HepG2(human liver cancer) and A549(human lung cancer) cells were tested using a 3-(4, 5-dimethyl-2-thiazolyl)-2, 5-diphenyl-2-H-tetrazolium bromide(MTT) method. The bioassay results demonstrate that compounds 3a and 3b display highly effective antiproliferative effects against MCF-7 cells with half maximal inhibitory concentration(IC₅₀) values of 10.83 and 7.62 μmol/L, respectively. Compound 3e exhibits preferable antiproliferative activities against A549 cells with an IC₅₀ value of 13.36 μmol/L, while compound 3f shows the best inhibitory effect against HepG2 cells with an IC₅₀ value of 8.55 μmol/L. Antitumor experiments show that the activities of these compounds are mainly affected by ionone and substituted groups in aromatic rings of chalcone.
- thiosemicarbazone,
- chalcone,
- ionone,
- antitumor activity,
- synthesis
1. [1]
  Zhu Y L, Song K K, Li Z C. Antityrosinase and Antimicrobial Activities of trans-Cinnamaldehyde Thiosemicarbazone[J]. J Agric Food Chem, 2009,57(12):5518-5523. doi: 10.1021/jf9007554
2. [2]
  Müjgan O, Cemil P, Taner A. Acid Dissociation Constants of Some Novel Isatin Thiosemicarbazone Derivatives[J]. J Chem Eng Data, 2010,55(8):2714-2718. doi: 10.1021/je9009738
3. [3]
  Doron C G, Zachary M, Elizabeth H. Synthesis and Structure-Activity Relationships of Parasiticidal Thiosemicarbazone Cysteine Protease Inhibitors Against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi[J]. J Med Chem, 2004,47(12):3212-3219. doi: 10.1021/jm030549j
4. [4]
  Subhash P, Zahra A, Ekk S. Antitumor Metallothiosemicarbazonates:Structure and Antitumor Activity of Palladium Complex of Phenanthrenequinone Thiosemicarbazone[J]. Inorg Chem, 2005,44(5):1154-1156. doi: 10.1021/ic048214v
5. [5]
  LIU Haibin, LV Ping, PAN Ningning. Synthesis and In vitro Anticancer Activity of Novel Quinazoline Derivatives Containing Thiosemicarbazone Structure[J]. Chem J Chinese Univ, 2014,35(5):981-988. doi: 10.7503/cjcu20130837
6. [6]
  LIU Lifeng, LI Peiyuan, QIAN Quanquan. Synthesis, Structure, Anticancer Activity of 2-Formylthiophene Thiosemicarbazones and Their Organometallic Ruthenium Complexes[J]. Chinese J Org Chem, 2013,33(4):854-859.
7. [7]
  Kalinowski D S, Yu Y, Sharpe P C. Design, Synthesis, and Characterization of Novel Iron Chelators:Structure-Activity Relationships of the 2-Benzoylpyridine Thiosemicarbazone Series and Their 3-Nitrobenzoyl Analogues as Potent Antitumor Agents[J]. J Med Chem, 2007,50(15):3716-3729. doi: 10.1021/jm070445z
8. [8]
  LIU Haibin, LV Ping, PAN Ningning. Synthesis and in vitro Antitumor Activity of 6-Chloro-4-piperazinquinazolinethiosemicarbazone Derivatives[J]. Chinese J Appl Chem, 2012,29(2):1000-1005.
9. [9]
  MIN Rui, FAN Xiaorui, ZHOU Pan. Synthesis, Crystal Structure, DNA Interaction and Antitumor Activity of Nickel(Ⅱ) Complex with Quinoline-2-carboxaldehyde N-4-Methyl-thiosemicarbazone[J]. Chinese J Inorg Chem, 2014,30(8):1771-1777.
10. [10]
  Khan S A, Asiri A M. Novel Steroidal (6R)-Spiaro-1, 3, 4-thiadiazoline Derivatives as Anti-bacterial Agents[J]. Chinese J Chem, 2012,30(8):1901-1905. doi: 10.1002/cjoc.v30.8
11. [11]
  FANG Xianwen, ZHOU Lizhen, CHENG Zhao. Synthesis, Crystal Strutures and Antitumor Activity of Novel Nitrogen Mustard-Linked Chalcones[J]. Chinese J Org Chem, 2013,33(3):523-529.
12. [12]
  Suryawanshi S N, Chandra N, Kumar P. Chemotherapy of Ieishmaniasis Part-Ⅷ:Synthesis and Bioevaluation of Novel Chalcones[J]. Eur J Med Chem, 2008,43(11):2473-2478. doi: 10.1016/j.ejmech.2007.12.014
13. [13]
  MENG Fanling, ZHENG Changji, LI Yinjing. Synthesis and Anti-bacterial Activity of Novel Chalcone Derivatives Containing 2, 4-Thiazolidinedione-3-acetic Acid Moiety[J]. Chinese J Org Chem, 2012,32(1):183-188.
14. [14]
  Szliszka E, Czuba Z P, Mazur B. Chalcones Enhance TRAIL-Induced Apoptosis in Prostate Cancer Cells[J]. Int J Mol Sci, 2010,11(1):1-13.
15. [15]
  Adams B K, Ferstl E M, Davis M C. Synthsis and Biological Evaluation of Novel Curcumin Analogs as Anti-cancer and Anti-angiogenesis Agents[J]. Bioorg Med Chem, 2004,12(14):3871-3783. doi: 10.1016/j.bmc.2004.05.006
16. [16]
  LIN Yuping, HU Chunyan, ZHENG Xi. Synthesis and Anti-tumor Activities of Novel 4'-(N-Substitued-1-piperazinyl)[J]. Chinese J Org Chem, 2017,37(1):237-341.
17. [17]
  Findik E, Dingil A, Karaman I. Synthesis of Terpenoid-Like Bischalcones from α-and β-Ionones and Their Biological Activities[J]. Synth Commun, 2009,39(24):4362-4374. doi: 10.1080/00397910902900696
18. [18]
  WU Jianzhang, WANG Cong, CAI Yuepiao. Synthesis, Crystal Structure, Antibacterial and Anti-Tumor Properties of Mono-carbonyl Analogues of Curcumin[J]. Chinese J Org Chem, 2010,30(6):884-889.
19. [19]
  LIU Changhui, WEN Ruiming, YE Xiaoqin. Synthesis and Characterization of Ionone-containing Chalcones[J]. Chinese J Appl Chem, 2012,29(7):780-783.
20. [20]
  Liu C, Zheng J, Deng L. Targeted Intracellular Controlled Drug Delivery and Tumor Therapy Through in Situ Forming Ag Nanogates on Mesoporous Silica Nanocontainers[J]. ACS Appl Mater Interfaces, 2015,7(22):11930-11938. doi: 10.1021/acsami.5b01787
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
3. [3]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
6. [6]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
7. [7]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
8. [8]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
9. [9]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
10. [10]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
11. [11]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
12. [12]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
13. [13]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
14. [14]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
15. [15]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
16. [16]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
17. [17]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
18. [18]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
19. [19]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
20. [20]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(819)
HTML views(136)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142