Citation: WANG Fang-Ming, HU Bing-Xiang, CHEN Chuan-Xiang, ZHOU Ze-Yu, BAO Dan, CHEN Li-Zhuang. Synthesis and Biological Activities of 10-Substituted 9-Aryl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-diones[J]. Chinese Journal of Structural Chemistry, ;2016, 35(3): 442-448. doi: 10.14102/j.cnki.0254-5861.2011-0915 shu

Synthesis and Biological Activities of 10-Substituted 9-Aryl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-diones

1.
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China

Corresponding author: WANG Fang-Ming,
Received Date: 28 July 2015
Available Online: 9 November 2015
Fund Project: This project was supported by National Natural Science Foundation of China for Young Scholars (No. 21201087) (No. 21201087)

A series of 10-substituted 9-aryl-3, 4, 6, 7, 9, 10-hexahydroacridine-1, 8(2H, 5H)-dione derivatives 2 were synthesized by a two-step reaction. All the compounds were characterized by IR, MS, and ¹H NMR. Crystals of 1a and 2c were obtained and determined by X-ray single-crystal diffraction. Crystal data of 1a: C₂₀H₂₂O₅, orthorhombic system, space group Pbcn, a = 15.8888(19), b = 18.228(2), c = 11.6926(13) Å, V = 3386.4(7) Å³, Z = 8, F(000) = 1456, D_c = 1.343 g/cm³, R = 0.0456 and wR = 0.1600. Crystal data of 2c: C₂₆H₂₄ClNO₃, monoclinic system, space group P2₁/n, a = 8.628(2), b = 10.912(3), c = 22.425(7) Å, β = 90.786(4)°, V = 2111.1(10) Å³, Z = 4, F(000) = 912, D_c = 1.365 g/cm³, R = 0.0613, and wR = 0.1196. The results of biological experiments show that compounds 2b and 2c could inhibit the proliferation of HepG2 cells.
- xanthenes,
- acridones,
- synthesis,
- crystal structure,
- biological activity
1. [1]
  (1) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2005, 22, 627-646.
2. [2]
  (2) Bernardino, A. M. R.; Castro, H. C.; Frugulhetti, L. C. P. P.; Loureiro, N. I. V.; Azevedo, A. R.; Pinheiro, L. C. S.; Souza, T. M. L.; Giongo, V.; Passamani, F.; Magalhaes, U. O.; Albuquerque, M. G.; Cabral, L. M.; Rodrigues; C. R. SAR of a series of anti-HSV-1 acridone derivatives, and a rational acridone-based design of a new anti-HSV-1 3H-benzo[b]pyrazolo[3, 4-h]-1, 6-naphthyridine series. Bioorg. Med. Chem. 2008, 16, 313-321.
3. [3]
  (3) Boumendjel, A.; Macalou, S.; Ahmed-Belkacem, A.; Blanc, M.; Pietro, A. D. Acridone derivatives: design, synthesis, and inhibition of breast cancer resistance protein ABCG2. Bioorg. Med. Chem. 2007, 15, 2892-2897.
4. [4]
  (4) Hegde, R.; Thimmaiah, P.; Yerigeri, M. C.; Krishnegowda, G.; Thimmaiah, K. N.; Houghton, P. J. Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells. Eur. J. Med. Chem. 2004, 39, 161-177.
5. [5]
  (5) Prasad, V. V. S. R.; Honeywell, R.; Rao, J. V.; Sathish, N. K.; Kumar, S. M. S.; Mayur, Y. C. Characteristic fragmentation behavior of some novel anti-calmodulin acridone derivatives studied by electrospray ionization tandem mass spectrometry. Int. J. Mass Spectrom. 2007, 263, 148-151.
6. [6]
  (6) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2008, 25, 166-187.
7. [7]
  (7) Jose, M. C.; Elena, P. M.; Abdelouahid, S.; Maria, C. C.; Elena, S. Recent advances in the Friedländer reaction. Chem. Rev. 2009, 109, 2652-2671.
8. [8]
  (8) Qiu, B.; Guo, L. H.; Chen, Z. T.; Chi, Y. W.; Zhang, L.; Chen, G. N. Synthesis of N-4-butylamine acridone and its use as fluorescent probe for ctDNA. Biosens. Bioelectron 2009, 24, 1281-1285.
9. [9]
  (9) Drlica, K.; Malik, M. Fluoroquinolones: actionand resistance. Curr. Top. Med. Chem. 2003, 3, 249-282.
10. [10]
  (10) Boumendjel, A.; Macalou, S.; Ahmed-Belkacem, A.; Blanc, M.; Pietro, A. D. Acridone derivatives: design, synthesis, and inhibition of breast cancer resistance protein ABCG2. Bioorg. Med. Chem. 2007, 15, 2892-2897.
11. [11]
  (11) Belmont, P.; Bosson, J.; Godet, T.; Tiano, M. Acridine and acridone derivatives, anticancer properties and synthetic methods: where are we now? Anti-Cancer Agents Med. Chem. 2007, 7, 139-169.
12. [12]
  (12) Goodell, J. R.; Ougolkov, A. V.; Hiasa, H.; Kaur, H.; Remmel, R.; Billadeau, D. D.; Ferguson, D. M. Acridine-based agents with topoisomerase II activity inhibit pancreatic cancer cell proliferation and induce apoptosis. J. Med. Chem. 2008, 51, 179-182.
13. [13]
  (13) Kaur, J.; Singh, P. Acridine derivatives: a patent review (2009 - 2010). Expert. Opin. Ther. Pat. 2011, 21, 437-454.
14. [14]
  (14) Goodell, J. R.; Madhok, A. A.; Hiasa, H.; Ferguson, D. M. Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity. Bioorg. Med. Chem. 2006, 14, 5467-5480.
15. [15]
  (15) Boulanger, C.; Di, G. C.; Vierling, P. Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection. Eur. J. Med. Chem. 2005, 40, 1295-1306.
16. [16]
  (16) Moore, M. J. B.; Schultes, C. M.; Cuesta, J.; Cuenca, F.; Gunaratnam, M.; Tanious, F. A.; Wilson, W. D.; Neidle, S. Trisubstituted acridines as G-quadruplex telomere targeting agents. Effects of extensions of the 3, 6- and 9-side chains on quadruplex binding, telomerase activity, and cell proliferation. J. Med. Chem. 2006, 49, 582-599.
17. [17]
  (17) Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. PCTInt. Appl. W O9706178 1997.
18. [18]
  (18) Shakibaei, G. I.; Mirzaei, P.; Bazgir, A. Dowex-50W promoted synthesis of 14-aryl-14H-dibenzo[a, j]xanthene and 1, 8-dioxo-octahydroxanthene derivatives under solvent-free conditions. Appl. Catal. A: Gen. 2007, 325, 188-192.
19. [19]
  (19) Hua, G. P.; Li, T. J.; Zhou, X.; Tu, S. J.; Zhu, S. L.; Zhang, X. J.; Ji, S. J.; Zhang, Y. One-pot synthesis of 9-aryl-1, 2, 3, 4, 5, 6, 7, 8, 9, 10-decahydro- 1, 8-acridinedione under microwave irradiation. Chin. J. Org. Chem. 2005, 25, 1294-1297.
20. [20]
  (20) Kaya, M.; Yildirir, Y.; Turker, L. Synthesis and laser activity of halo-acridinedione derivatives. J. Heterocyclic. Chem. 2009, 46, 294-297.
21. [21]
  (21) Software packages SMART and SAINT, Bruker AXS Inc., Madison, WI (2000).
22. [22]
  (22) Sheldrick. G. M. SHELXL-97, Program for the Refinement of Crystal Structure. University of Gottingen, Germany 1997.
23. [23]
  (23) Zhao, B.; Ge, J. F.; Zhu, J. J.; Huang, X. H.; Li, J. Calculation methods in evaluation of cell proliferation inhibition rate in MTT tests. Anhui Med. Pharm. 2007, 11, 834-836.
24. [24]
  (24) Ougolkov, A. V.; Fernandez-Zapico, M. E.; Savoy, D. N.; Urrutia, R. A.; Billadeau, D. D. Glycogen synthesis Kinase-3β participates in nuclear factor B-mediated gene transcription and cell survival in Pancreatic cancer cells. Cancer Res. 2005, 65, 2076-2081.
1. [1]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
2. [2]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
3. [3]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
4. [4]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
5. [5]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
6. [6]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
7. [7]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
8. [8]
  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
9. [9]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
10. [10]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
11. [11]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
12. [12]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
13. [13]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
14. [14]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
15. [15]
  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
16. [16]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
17. [17]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
18. [18]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
19. [19]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
20. [20]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(718)
HTML views(17)

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