A Novel Definition of Molecular Connectivity Index for QSPR/QSAR Studies on the Physicochemical Properties and Bioactivity of Organic Compounds

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (5): 525-536. Previous Articles Next Articles

新定义的价连接性指数与有机物理化活性的相关性研究

杨道武^a, 余训民^*,b

^a长沙电力学院化学系长沙 410077
^b武汉化工学院环境与城市建设学院武汉 430073

收稿日期:2003-06-26 修回日期:2003-09-05 接受日期:2003-11-26 发布日期:2022-09-20
基金资助:
湖北省教育厅自然科学基金重点(No. 2003A1001)资助项目.

A Novel Definition of Molecular Connectivity Index for QSPR/QSAR Studies on the Physicochemical Properties and Bioactivity of Organic Compounds

YANG, Dao-Wu^a, YU, Xun-Min^*,b

^aDepartment of Chemistry, Changsha University of Electric Power, Changsha 410077
^bCollege of Environment and Civil Engineering, Wuhan Institute of Chemical Technology, Wuhan 430073

Received:2003-06-26 Revised:2003-09-05 Accepted:2003-11-26 Published:2022-09-20
Contact: *E-mail: xunminyu009@sohu.com

Abstract

The valence delta δ^Y_i based on the structural characteristicbondingatom i (i.e. the four quantum number n_i, family number of periodic table N_i and electron number of valence Z_i and lone pair p_i, etc.) and itschemical surroundings (through the considering contribution of adjoining bonding atom j or hydrogen atom number h_i, i.e. connecting other bonding atom number m_i, number of bonding electrons M_i, hybridization mode of atoms i (L_i) and j (L_j) to δ^Y_i, etc.) of molecule is defined: δ^Y_i=[m_iZ_i(Z_i-h_i)+∑(L_iL_j)]/[(M_i-h_i)(L_i＋p_i)(n_i-1)]. Based on the adjacency index, a novel molecular structure information connectivity index^mω^Y that can show the multiple bonds, heteroatom-containing compounds were proposed: ^mω^Y=∑∏(δ^Y_i)^0.5_j, in which ⁰ω^Yand ¹ω^Y are defined as ⁰ω^Y=∑(δ^Y_i)^0.5 and ¹ω^Y=∑(δ^Y_iδ^Y_j)^0.5. ⁰ω^Y and ¹ω^Y are ease to be calculated and have good discrimination between isomeric organic compounds. A series of physicochemical properties and bioactivities of some type of organic compounds are highly correlated with ⁰ω^Y, ¹ω^Y and the number N_Cof carbon atoms, and most properties or activities are well in models, which could provide satisfactory estimation prediction for a series of physicochemical properties and bioactivities of some type of organic compounds. The predicted results of new models were in agreement with experiments finding out that ⁰ω^Y, ¹ω^Y and N_C with different extent act on different properties. It has been demonstrated that the method possesses the advantage of easy computation and clear physical significance. The estimated results with above QSPR/QSAR models are all better than the relevant achievements of literatures. All these results show that the connectivity index ^mω^Y of edge valence is an important parameter in QSPR/QSAR studies.

Key words: connectivity index, organic compound, valence delta, physical and chemical property,biological activity, QSPR/QSAR

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YANG, Dao-Wu, YU, Xun-Min. A Novel Definition of Molecular Connectivity Index for QSPR/QSAR Studies on the Physicochemical Properties and Bioactivity of Organic Compounds[J]. Chinese Journal of Organic Chemistry, 2004, 24(5): 525-536.

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References

1 Jiang, Z.-P. Sci. China, Ser. 2001, 53(6), 15 (in Chinese).
(蒋展鹏, 科学, 2001, 53(6), 15.)
2 Wang, L.-S.; Han, S.-K. Progress of Organic Contaminants Chemistry, Chemical Industry Press, Beijing, 1998, pp. 1～7;p. 70; p. 83; p. 134; p. 139 (in Chinese).
(王连生, 韩朔睽, 有机污染化学进展, 化学工业出版社, 北京, 1998, pp. 1～7; p. 70; p. 83; p. 134; p. 139.)
3 Kier, L.-B.; Hall, L. H. Molecular Connectivity in StructureActivity Analysis, Academic Press, New York, 1986.
4 Xu, L.; Hu, C.-Y. The Applications of Graph Theory in Chemistry, Science Press, Beijing, 2000, pp. 148～169 (in Chinese).
(许禄, 胡昌玉, 应用化学图论, 科学出版社, 北京, 2000, pp. 148～169.)
5 Xin, H.-W. Molecular Topology, Chinese University of Science Technoldgy Press, Hefei, 1991 (in Chinese).
(辛厚文, 分子拓扑学, 中国科学技术大学出版社,合肥, 1991.)
6 Feng, C.-J.; Mu, L.-L. Chemistry 2003, 66(2), 125 (in Chinese).
(冯长君, 沐涞龙, 化学通报, 2003, 66(2), 125.)
7 Wang, H.-Y.; Jiang, Y.-S. Chemistry 1992,54(1), 6 (in Chinese).
(王化云, 江元生, 化学通报, 1992,54(1), 6.)
8 Qi, Y.-H.; Yang, J.-A.; Xu, L. Chin. J. Anal. Chem. 2000, 28(2), 223 (in Chinese).
(齐玉华, 杨家安, 许禄, 分析化学, 2000, 28(2), 223.)
9 Cao, C.-Z.; Yang, H. Chin. J. Org. Chem. 2002,22(5), 354 (in Chinese).
(曹晨忠, 袁华, 有机化学, 2002, 22(5), 354.)
10 Yu, X.-M. Chin. J. Org. Chem. 2001, 21(9), 658 (in Chinese).
(余训民, 有机化学, 2001, 21(9), 658.)
11 Yu, X.-M. Chromatography 2002, 20(1), 6 (in Chinese).
(余训民, 色谱, 2002, 20(1), 6.)
12 Feng, C.-J.; Chen, Y.; Du, X.-H. J. Jilin Univ. (Nat. Sci. Ed.)2000, (3), 80 (in Chinese).
(冯长君, 陈艳, 堵锡华, 吉林大学自然科学学报,2000, (3), 80.)
13 Zhu, X.-Z.; Zhu, C.-Z.; Weng, D.-S. Acta Chim. Sinica 1995, 53, 444 (in Chinese).
(朱鑫璋, 朱昌中, 翁党生, 化学学报, 1995, 53, 444.)
14 Du, X.-H.; Luo, S.-P. J. Sichuan Univ. (Nat. Sci. Ed.) 2000, 38(5), 708 (in Chinese).
(堵锡华, 罗士平, 四川大学学报(自然科学版), 2000, 38(5), 708.)
15 Luo, B.-P.; Peng, X.-C.; Ren, B.-Y. J. Jishou Univ. (Nat. Sci. Ed.) 2000, 21(1), 43 (in Chinese).
(罗北平, 彭晓春, 任碧野, 吉首大学学报(自然科学版), 2000, 21(1), 43.)
16 Ren, B.-Y.; Xu, Y.; Chen, G.-B. Acta Chim. Sinica 1999, 57(6), 563 (in Chinese).
(任碧野, 许友, 陈国斌, 化学学报, 1999, 57(6), 563.)
17 Lin, Z.-H.; Xu, J.-H.; Liu, S.-S. Acta Phys.-Chim. Sin. 2000, 16(2), 153 (in Chinese).
(林志华, 胥江河, 刘树深, 物理化学学报, 2000, 16(2), 153.)
18 Ni, C.-H.; Feng, Z.-Y. Huagong Xuebao 1997, 48, 227 (in Chinese).
(倪才华, 冯致云, 化工学报, 1997,48, 227.)
19 Zhang, X.-D.; Zhan, Q.-Y.; Zhao, L.-Q. Chemistry 1995, 57(6), 52 (in Chinese).
(张向东, 詹庆云, 赵立群, 化学通报, 1995, 57(6), 52.)
20 Zhu, C.-Z.; Zhu, X.-Z. Chemistry 1995, 57(1), 15 (in Chinese).
(朱昌中, 朱鑫璋, 化学通报, 1995,57(1), 15.)
21 Needhan, D.-E.; Wer, C.; Dubos, J.-E. J. Am. Chem. Soc. 1988, 111, 4186.
22 Kang, J.-J.; Cao, C.-Z.; Li, Z.-L. J. Xingtan Normal Univ. (Nat.Sci. Ed.) 1997, 18(3), 7 (in Chinese).
(康继军, 曹晨忠, 李志良, 湘潭师范学院学报(自然科学版), 1997, 18(3), 7.)
23 Du, X.-H.; Feng, C.-J. J. Fuzhou Univ. (Nat. Sci. Ed.) 2001, 29(2), 92 (in Chinese).
(堵锡华, 冯长君, 福州大学学报(自然科学版), 2001, 29(2), 92.)
24 Yang, F.; Yan, X.-C.; Luo, M.-D. Chin. J. Chem. Phys. 1998, 11(3), 221 (in Chinese).
(杨锋, 颜肖慈, 罗明道, 化学物理学报, 1998, 11(3), 221.)
25 Yang, F. ; Luo, M.-D.; Yan, X.-C. Chin. J. Org. Chem. 2000, 20(3), 410 (in Chinese).
(杨锋, 罗明道, 颜肖慈, 有机化学, 2000, 20(3), 410.)
26 Du, X.-H. Chemistry 2001, 64(8),508 (in Chinese).
(堵锡华, 化学通报, 2001, 64(8), 508.)
27 Wang, L.-S.; Zhi, L.-Z.; Gao, S.-T. Molecular Structure and Chromatography Retention, Chemical Industry Press, Beijing, 1994, pp. 233～238 (in Chinese).
(王连生, 支良正, 高松亭, 分子结构与色谱保留,化学工业出版社, 北京, 1994, pp. 233～238.)
28 Wang, L.-S. Organic Contaminants Chemistry(2) , Science Press, Beijing, 1991, p. 163 (in Chinese).
(王连生, 有机污染物化学(2), 化学工业出版社,北京, 1991, p. 163.)
29 Department of Analytical Chemistry, Chengdou University of Science Technology, The Handbook of Analytical Chemistry(4). Chemical Industry Press, Beijing, 1984, p. 695 (in Chinese).
(成都科技大学分析化学教研室, 分析化学手册(第四分册), 化学工业出版社, 北京, 1984, p. 695.)
30 Weast, R.-C. CRC Handbook of Chemistry and Physics, 58th ed., CRCPress, Ohio, 2000, p. 81.

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新定义的价连接性指数与有机物理化活性的相关性研究

A Novel Definition of Molecular Connectivity Index for QSPR/QSAR Studies on the Physicochemical Properties and Bioactivity of Organic Compounds

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