Citation: Wang Shenghong, Han Xiao, Mao Ting, Zeng Huijun, Chen Rui, Chen Huiqiong. Synthesis and Antitumor Activity Evaluation of Novel Tetrahydrobenzo[4', 5']thieno[3', 2': 5, 6]pyrido[4, 3-d]pyrimidine Derivatives[J]. Chemistry, ;2019, 82(7): 623-629. shu

Synthesis and Antitumor Activity Evaluation of Novel Tetrahydrobenzo[4', 5']thieno[3', 2': 5, 6]pyrido[4, 3-d]pyrimidine Derivatives

1.
Changjiang Polytechnic, Wuhan 430064
2.
Wuhan Institute for Food and Cosmetic Control, Wuhan 430012
3.
Wuhan Institute of Technology, Wuhan 430205
4.
Wuhan Aimin Pharmaceutical Limited company, Ezhou 436070

Corresponding author: Han Xiao, hxiao12378@126.com
Received Date: 24 February 2019
Accepted Date: 16 March 2019

Figures(1)

A series of novel tetrahydrobenzo[4', 5']thieno[3', 2':5, 6]pyrido[4, 3-d]pyrimidine derivatives were designed and synthesized via a tandem aza-Wittig reaction, and their anti-tumor activities in vitro were evaluated for CNE2, KB, MGC-803, MCF-7 and PC3 cells by MTT assay. The preliminary biological results showed that these conjugates display significant antiproliferative effect on these five cancer cells, especially for MGC-803. Compound 8c (IC₅₀=0.9±0.25μmol·L^-1) stood out as the most potent compound against MGC-803, and is 20 times more active than 5-FU (IC₅₀=18.4±1.43μmol·L^-1). Additionally, all compounds were nontoxic to health GES-1 and VERO cells, while 5-FU showed essential toxicity. Tetrahydrobenzo[4', 5'] thieno[3', 2':5, 6] pyrido[4, 3-d] pyrimidine compounds displayed good anti-tumor activity and deserved further research.
- Aza-Wittig reaction,
- Tetrahydrobenzo[4', 5']thieno,
- [3', 2':5, 6]Pyrido[4, 3-d]pyrimidine,
- Antitumor
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
  C H Wu, M S Coumar, C Y Chu et al. J. Med. Chem., 2010, 53(20):7316-7326.
8. [8]
9. [9]
  Q Y Ren, Y J Liang, H W He et al. Bioorg. Med. Chem. Lett., 2009, 19(23):6713-6716.
10. [10]
11. [11]
  A T Mavrova, S Dimov, D Yancheva et al. Eur. J. Med. Chem., 2016, 123:69-79.
12. [12]
  H Abe, S Kikuchi, K Hayakawa et al. ACS Med. Chem. Lett., 2011, 2(4):320-324.
13. [13]
  W Zhou, X F Liu, Z C Tu et al. J. Med. Chem., 2013, 56(20):7821-7837.
14. [14]
  J Lou, Z Liu, Y Li et al. Bioorg. Med. Chem. Lett., 2011, 21(22):6662-6666.
15. [15]
  Y Loidreau, P Marchand, C Dubouilh-Benard et al. Eur. J. Med. Chem., 2012, 58:171-183.
16. [16]
  W Y Mo, Y J Liang, Y C Gu et al. Bioorg. Med. Chem. Lett., 2011, 21(19):5975-5977.
17. [17]
  L Aurelio, C Valant, H Figler et al. Bioorg. Med. Chem., 2009, 17(20):7353-7361.
18. [18]
  Y Ai, Y J Liang, J C Liu et al. Eur. J. Med. Chem., 2012, 47(1):206-213.
19. [19]
  P K Muller, M N Molton. Nat. Rev. Drug Discov., 2012, 11(10):751-761.
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]
  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
3. [3]
  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
4. [4]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
5. [5]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
6. [6]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
7. [7]
  Haitao Wang , Lianglang Yu , Jizhou Jiang , Arramel , Jing Zou . S-Doping of the N-Sites of g-C₃N₄ to Enhance Photocatalytic H₂ Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(5): 2305047-0. doi: 10.3866/PKU.WHXB202305047
8. [8]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
9. [9]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
10. [10]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
11. [11]
  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
12. [12]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
13. [13]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
14. [14]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
15. [15]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
16. [16]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-0. doi: 10.3866/PKU.WHXB202408002
17. [17]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
18. [18]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
19. [19]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-0. doi: 10.1016/j.actphy.2025.100052
20. [20]
  Jiawei Hu , Kai Xia , Ao Yang , Zhihao Zhang , Wen Xiao , Chao Liu , Qinfang Zhang . Interfacial Engineering of Ultrathin 2D/2D NiPS₃/C₃N₅ Heterojunctions for Boosting Photocatalytic H₂ Evolution. Acta Physico-Chimica Sinica, 2024, 40(5): 2305043-0. doi: 10.3866/PKU.WHXB202305043

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(614)
HTML views(133)

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