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
-
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.
-
-
-
[1]
(1) Hammond, G. S. Norris Award Lecture, 1968.
-
[2]
(2) Michielan, L.; Moro, S. J. Chem. Inf. Model. 2010, 50, 961. doi: 10.1021/ci100072z
-
[3]
(3) Khan, M. T.; Sylte, I. Curr. Drug Discovery Technol. 2007, 4, 141. doi: 10.2174/157016307782109706
-
[4]
(4) Mager, D. E. Adv. Drug Delivery Rev. 2006, 58, 1326. doi: 10.1016/j.addr.2006.08.002
-
[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) Basak, S. C.; Mills, D. SAR QSAR Environ. Res. 2001, 12, 481. doi: 10.1080/10629360108039830
-
[7]
(7) Gute, B. D.; Balasubramanian, K.; Geiss, K. T.; Basak, S. C. Environ Toxicol Pharmacol, 2004, 16, 121.
-
[8]
(8) Restrepo, G.; Basak, S. C.; Mills, D. Curr. Comput. Aided Drug Des. 2011, 7, 109. doi: 10.2174/157340911795677639
-
[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) 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) Basak, S. C.; Mills, D.; Gute, B. D.; Natarajan, R. Top Heterocycl. Chem. 2006, 3, 39.
-
[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) 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) Gu, C.; odarzi, M.; Yang, X.; Bian, Y.; Sun, C.; Jiang, X. Toxicol. Lett. 2012, 208, 269.
-
[15]
(15) Hankinson, O. Arch. Biochem. Biophys. 2005, 433, 379. doi: 10.1016/j.abb.2004.09.031
-
[16]
(16) Basak, S. C.; Mills, D.; Mumtaz, M. M.; Balasubramanian, K. Indian J. Chem. 2003, 42A, 1385.
-
[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) 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) Wang, Q.; Ma, P. S.; Jia, Q. Z.; Xia, S. Q. J. Chem. Eng. Data 2008, 53, 1103. doi: 10.1021/je700641j
-
[20]
(20) Wang, Q.; Jia, Q. Z.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 169. doi: 10.1021/je200971z
-
[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) 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) Yan, F.; Xia, S.;Wang, Q.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 805. doi: 10.1021/je201023a
-
[24]
(24) Yan, F.; Xia, S.;Wang, Q.; Ma, P. S. J. Chem. Eng. Data 2012, 57, 2252. doi: 10.1021/je3002046
-
[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) So, S. S.; Karplus, M. J. Med. Chem. 1997, 40, 4360.
-
[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]
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
-
[2]
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
-
[3]
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): 100012-. doi: 10.3866/PKU.WHXB202309027
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
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
-
[8]
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
-
[9]
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
-
[10]
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
-
[11]
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): 100010-. doi: 10.3866/PKU.WHXB202309041
-
[12]
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
-
[13]
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
-
[14]
Ying Zhang , Fang Ge , Zhimin Luo . AI-Driven Biochemical Teaching Research: Predicting the Functional Effects of Gene Mutations. University Chemistry, 2025, 40(3): 277-284. doi: 10.12461/PKU.DXHX202412104
-
[15]
Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
-
[16]
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
-
[17]
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
-
[18]
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
-
[19]
Cuicui Yang , Bo Shang , Xiaohua Chen , Weiquan Tian . Understanding the Wave-Particle Duality and Quantization of Confined Particles Starting from Classic Mechanics. University Chemistry, 2025, 40(3): 408-414. doi: 10.12461/PKU.DXHX202407066
-
[20]
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
-
[1]
Metrics
- PDF Downloads(563)
- Abstract views(674)
- HTML views(5)