Citation: ZHU Zhi-Chen, WANG Qiang, JIA Qing-Zhu, XIA Shu-Qian, MA Pei-Sheng. Structure-Property Relationship for the Pharmacological and Toxicological Activity of Heterocyclic Compounds[J]. Acta Physico-Chimica Sinica, ;2014, 30(6): 1086-1090. doi: 10.3866/PKU.WHXB201404161 shu

Structure-Property Relationship for the Pharmacological and Toxicological Activity of Heterocyclic Compounds

1.
1 School of Science, Tianjin University of Urban Construction, Tianjin 300384, P. R. China;
2 School of Material Science and Chemical Engineering, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
3 School of Marine Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
4 School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China

Received Date: 14 January 2014
Available Online: 16 April 2014
Fund Project:

Heterocyclic molecules play a crucial role in health care and in pharmaceutical drug design. A large number of drugs used in Western medical practice are heterocyclic molecules. In this study, a set of norm indexes of the extended distance matrix are proposed. From these a stable and accurate structureproperty relationship model was developed for the prediction of the aryl hydrocarbon receptor binding affinity (pEC₅₀) of dibenzofurans and the mutagenic potency (lnR) of aromatic and heteroaromatic amines. Our results indicate that the new model, based on these norm indexes, provides very satisfactory results, and that the average absolute differences for pEC₅₀ prediction and lnR prediction were 0.403 and 0.702 with r² (square correlation coefficient) values of 0.876 and 0.779, respectively. A comparison of these results with other methods demonstrates that our method, based only on the same mathematical model, performed better in terms of both accuracy and stability.
- Dibenzofuran,
- Aromatic and heteroaromatic amine,
- Aryl hydrocarbon receptor affinity,
- Mutagenic potency,
- Structure-property relationship,
- Norm index,
- Prediction
1. [1]
  
  (1) Hammond, G. S. Norris Award Lecture, 1968.
2. [2]
  (2) Michielan, L.; Moro, S. J. Chem. Inf. Model. 2010, 50, 961. doi: 10.1021/ci100072z
3. [3]
  (3) Khan, M. T.; Sylte, I. Curr. Drug Discovery Technol. 2007, 4, 141. doi: 10.2174/157016307782109706
4. [4]
  (4) Mager, D. E. Adv. Drug Delivery Rev. 2006, 58, 1326. doi: 10.1016/j.addr.2006.08.002
5. [5]
  (5) Zhu, H.; Tropsha, A.; Fourches, D.; Varnek, A.; Papa, E.; Gramatica, P.; Oberg, T.; Dao, P.; Cherkasov, A.; Tetko, I. V. J. Chem. Inf. Model. 2008, 48, 766. doi: 10.1021/ci700443v
6. [6]
  (6) Basak, S. C.; Mills, D. SAR QSAR Environ. Res. 2001, 12, 481. doi: 10.1080/10629360108039830
7. [7]
  (7) Gute, B. D.; Balasubramanian, K.; Geiss, K. T.; Basak, S. C. Environ Toxicol Pharmacol, 2004, 16, 121.
8. [8]
  (8) Restrepo, G.; Basak, S. C.; Mills, D. Curr. Comput. Aided Drug Des. 2011, 7, 109. doi: 10.2174/157340911795677639
9. [9]
  (9) Basak, S. C.; Mills, D. R.; Balaban, A. T.; Gute, B. D. J. Chem. Inf. Comput. Sci. 2001, 41, 671. doi: 10.1021/ci000126f
10. [10]
  (10) davarthy, S. S.; Robinson, R. L., Jr.; Gasem, K. A. M. Fluid Phase Equilib. 2008, 264, 122. doi: 10.1016/j.fluid.2007.11.003
11. [11]
  (11) Basak, S. C.; Mills, D.; Gute, B. D.; Natarajan, R. Top Heterocycl. Chem. 2006, 3, 39.
12. [12]
  (12) Li, X. L.; Ye, L.;Wang, X. X.;Wang, X. Z.; Liu, H. L.; Qian, X. P.; Zhu, Y. L.; Yu, H. X. Sci. Total Environ. 2012, 441, 230. doi: 10.1016/j.scitotenv.2012.08.072
13. [13]
  (13) Doering, J. A.;Wiseman, S.; Beitel, S. C.; Giesy, J. P.; Hecker, M. Aquat. Toxicol. 2014, 150, 27. doi: 10.1016/j.aquatox.2014.02.009
14. [14]
  (14) Gu, C.; odarzi, M.; Yang, X.; Bian, Y.; Sun, C.; Jiang, X. Toxicol. Lett. 2012, 208, 269.
15. [15]
  (15) Hankinson, O. Arch. Biochem. Biophys. 2005, 433, 379. doi: 10.1016/j.abb.2004.09.031
16. [16]
  (16) Basak, S. C.; Mills, D.; Mumtaz, M. M.; Balasubramanian, K. Indian J. Chem. 2003, 42A, 1385.
17. [17]
  (17) Basak, S. C.; Mills, D.; Gute, B. D.; Hawkins, D. M. Predicting Mutagenicity of Congeneric and DiverseSets of Chemicals Using Computed Molecular Descriptors: a Hierarchical Approach. In Benigni R(ed) Quantitative Structure -Activity Relationship (QSAR) Models of Mutagens and Carcinogens; CRC: Boca Raton, FL, 2003; pp 207-208.
18. [18]
  (18) Cao, F.; Li, X.; Ye, L.; Xie, Y.;Wang, X.; Shi,W.; Qian, X.; Zhu, Y.; Yu, H. Environ. Toxicol. Pharmacol. 2013, 36, 626. doi: 10.1016/j.etap.2013.06.004
19. [19]
  (19) Wang, Q.; Ma, P. S.; Jia, Q. Z.; Xia, S. Q. J. Chem. Eng. Data 2008, 53, 1103. doi: 10.1021/je700641j
20. [20]
  (20) Wang, Q.; Jia, Q. Z.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 169. doi: 10.1021/je200971z
21. [21]
  (21) Jia, Q. Z.;Wang, Q.; Ma, P. S.; Xia, S. Q.; Yan, F. Y.; Tang, H. M. J. Chem. Eng. Data 2012, 57, 3357. doi: 10.1021/je301070f
22. [22]
  (22) Zhu, Z. C.;Wang, Q.; Jia, Q. Z.; Tang, H. M.; Ma, P. S. Acta Phys. -Chim. Sin. 2013, 29 (1), 30. [朱志臣, 王强, 贾青竹, 汤红梅, 马沛生. 物理化学学报, 2013, 29 (1), 30.] doi: 10.3866/PKU.WHXB201210265
23. [23]
  (23) Yan, F.; Xia, S.;Wang, Q.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 805. doi: 10.1021/je201023a
24. [24]
  (24) Yan, F.; Xia, S.;Wang, Q.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 2252. doi: 10.1021/je3002046
25. [25]
  (25) Wang, Q.; Jia, Q. Z.; Yan, L. H.; Ma, P. S.; Xia, S. Q. doi: 10.1016/j.chemosphere.2014.02.030
26. [26]
  (26) So, S. S.; Karplus, M. J. Med. Chem. 1997, 40, 4360.
27. [27]
  (27) Debnath, A. K.; Debnath, G.; Shusterman, A. J.; Hansch, C. A. Environ. Mol. Mutagen. 1992, 19, 37. doi: 10.1002/em.2850190107
1. [1]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
2. [2]
  Haiying Jiang , Liuhong Song , Yangyang Cheng , Kefen Yue , Mingli Peng , Huilin Guo . Ph―C≡C―Cu_2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003
3. [3]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
4. [4]
  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
5. [5]
  Xue-Peng Zhang , Yuchi Long , Yushu Pan , Jiding Wang , Baoyu Bai , Rui Ding . 定量构效关系方法学习探索：以钴卟啉活化氧气为例. University Chemistry, 2025, 40(8): 345-359. doi: 10.12461/PKU.DXHX202410107
6. [6]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
7. [7]
  Haiyu Zhu , Zhuoqun Wen , Wen Xiong , Xingzhan Wei , Zhi Wang . 二维半金属/硅异质结中肖特基势垒高度的准确高效预测. Acta Physico-Chimica Sinica, 2025, 41(7): 100078-0. doi: 10.1016/j.actphy.2025.100078
8. [8]
  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
9. [9]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
10. [10]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
11. [11]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
12. [12]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
13. [13]
  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
14. [14]
  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
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]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
17. [17]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
18. [18]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
19. [19]
  Yujia Luo , Yunpeng Qi , Huiping Xing , Yuhu Li . The Use of Viscosity Method for Predicting the Life Expectancy of Xuan Paper-based Heritage Objects. University Chemistry, 2024, 39(8): 290-294. doi: 10.3866/PKU.DXHX202401037
20. [20]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 2309041-0. doi: 10.3866/PKU.WHXB202309041

Get Citation

PDF

XML

Metrics

PDF Downloads(563)
Abstract views(743)
HTML views(8)

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