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Theoretical research of antitumor activities of s-triazole fusedheterocycle derivatives of fluoroquinolone(PDF)

《南京理工大学学报》(自然科学版)[ISSN:1005-9830/CN:32-1397/N]

Issue:
2017年03期
Page:
393-
Research Field:
Publishing date:

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Title:
Theoretical research of antitumor activities of s-triazole fusedheterocycle derivatives of fluoroquinolone
Author(s):
Feng Hui1Feng Changjun1Wang Zhirong2
1.School of Chemistry and Chemical Engineering,Xuzhou Institute of Technology,Xuzhou 221111,China; 2.Department of Cardiology,Affiliated Hospital of Xuzhou Medical College,Xuzhou 221002,China
Keywords:
s-triazole fused heterocycle derivative of fluoroquinolone Chinese hamster ovary mice leukemia cell human leukemic cell antitumor activity quantitative structure-activity relationship models
PACS:
R914; R979.1
DOI:
10.14177/j.cnki.32-1397n.2017.41.03.018
Abstract:
Quantitative structure-activity relationships(QSAR)models of the antitumor activities(Aj:AC,ALand AH)and quantum chemical parameters Qt for Chinese hamster ovary(CHO),Mice leukemia cell(L1210),Human leukemic cell(HL60)are set up to study the antitumor mechanisms at the microscale of 15 s-triazole fused heterocycle derivatives of fluoroquinolone(FQTHs).The quantum chemical parameters(Qt,such as EHOMO,ELUMO,μ,QCd,QNe,QOf,QF and QS)of the above mentioned compounds are calculated using the MOPAC-AM1 method.The QSAR models of the antitumor activities for FQTHs are established using leaps-and-bounds regression.The correlation coefficients(R2)and leave-one-out(LOO)cross validation R2cv of the optimal three-parameter QSAR models are 0.910 and 0.827 for AC model,0.874 and 0.815 for AL model,0.941 and 0.894 for AH model,respectively.The QSAR models have both favorable robustness and good prediction capability by R2,R2adj,F,R2cv,VIF,AIC,FIT tests.The QSAR models mentioned above show that QCd,QNe,QOf and μ affect the antitumor activity directly.

References:

[1] 屈凌波,刘艳,郭宗儒.氟喹诺酮类药物构效关系的研究进展[J].中国药物化学杂志,2001,11(4):241-244.
Qu Lingbo,Liu Yan,Guo Zongru.Advances in the study on the quantitative structure activity relationship of fluoroquinolones[J].Chinese Journal of Medicinal Chemistry,2001,11(4):241-244.
[2]许秋菊,侯莉莉,毋小魁,等.环丙氟喹诺酮C3/C7双腙的合成及抗肿瘤活性[J].中国医科大学学报,2013,44(1):35-38.
Xu Qiuju,Hou Lili,Wu Xiaokui,et al.Synthesis and antitumor activity of ciprofloquinolone bis-(C3/C7 hydrazone)s[J].Journal of China Pharmaceutical University,2013,44(1):35-38.
[3]高丽,李文凤,梁军,等.右丙亚胺对表柔比星诱导乳腺癌细胞凋亡影响的研究[J].中华肿瘤防治杂志,2013,20(12):914-917.
Gao Li,Li Wenfeng,Liang Jun,et al.Influence of dexrazoxane on epirubicin cytotoxicity in human breast cancer cell lines[J].Chin J Cancer Prev Treat,2013,20(12):914-917.
[4]李启凤,吴名耀.食管癌组织TopoⅡα和MGMT表达及其临床意义的研究[J].中华肿瘤防治杂志,2010,17(22):1818-1820.
Li Qifeng,Wu Mingyao.Expression and clinical significance of TopoⅡα and MGMT in esophageal carcinoma tissues[J].Chin J Cancer Prev Treat,2010,17(22):1818-1820.
[5]谢松强,陈寅生,王国强,等.Part Ⅳ.环丙沙星C-3羧基衍生物均三唑并噻二嗪及吡唑并均三唑的合成和抗肿瘤活性研究[J].药学学报,2012,47(1):66-71.
Xie Songqiang,Chen Yinsheng,Wang Guoqiang,et al.Part Ⅳ.Synthesis and antitumor evaluation of s-triazolothiadiazines and pyrazolo s-triazoles derived from ciproxacin[J].Acta Pharmaceutica Sinica,2012,47(1):66-71.
[6]Domagala J M,Hann L D,Heifetz C L.New structure-activity relationships of the quinolone antibacterials using the target enzyme.The development and application of a DNA gyrase assay[J].J Med Chem,1986,29(3):394-404.
[7]Feng Changjun,Yang Weihua.Linear QSAR regression models for the prediction of bioconcentration factors of chloroanilines in fish by density functional theory[J].Chinese J Struct Chem,2014,33(6):830-834.
[8]Basant N,Gupta S,Singh K P.Predicting human intestinal absorption of diverse chemicals using ensemble learning based QSAR modeling approaches[J].Comput Biol Chem,2016,61(1):178-196.
[9]冯长君,堵锡华,沐来龙.用新型连接性指数与神经网络预测取代苯酚和取代苯甲酸生物降解性[J].南京理工大学学报,2009,33(5):700-706.
Feng Changjun,Du Xihua,Mu Lailong.Prediction of biodegradability of substituted phenols and benzoic acids with novel molecular connectivity index and artificial neural network[J].Journal of Nanjing University of Science and Technology,2009,33(5):700-706.
[10]Huang Xiangfeng,Feng Yi,Hu Cui,et al.Mechanistic QSAR models for interpreting degradation rates of sulfonamides in UV-photocatalysis systems[J].Chemosphere,2015,138(1):183-189.
[11]冯长君.3-取代硫基-5-(2-羟基苯基)-4H-1,2,4-三唑类化合物抑菌活性的定量构效关系和结构修饰的理论研究[J].化学学报,2012,70(4):512-518.
Feng Changjun.Theoretical studies on quantitative structure-activity relationship and structural modifi-cation for 3-substituted sulfur-5-(2-hydroxyphenyl)-4H-1,2,4-triazole compounds[J].Acta Chimica Sinica,2012,70(4):512-518.
[12]冯长君.苯异丙基胺类兴奋剂兴奋强度理论研究[J].深圳大学学报(理工版),2012,29(1):67-72.
Feng Changjun.Theoretical studies on the action strength of DOM of phenyl-isopropylamine dopes[J].Journal of Shenzhen University Science and Engineering,2012,29(1):67-72.
[13]陈学勇,韦朝海,邓秀琼,等.硝基芳烃对梨形四膜虫毒性的定量构效关系解析[J].化学学报,2011,69(21):2618-2626.
Chen Xueyong,Wei Chaohai,Deng Xiuqiong,et al.An analysis of the toxicity of nitroaromatic compounds to tetrahymena pyriformis using the quantitative structure activity relationship method[J].Acta Chimica Sinica,2011,69(21):2618-2626.
[14]徐芳荣,李江波.5-苯基-1-苯氨基-1-氢-咪唑衍生物的定量结构细胞毒性关系[J].药学学报,2010,45(2):274-278.
Xu Fangrong,Li Jiangbo.Quantitative structure-cytotoxicity relationship of anti-HIV 5-phenyl-1-phenylamino-1H-imidazole derivatives[J].Acta Pharmaceutica Sinica,2010,45(2):274-278.
[15]Douglas M H,Subhash C B,Denise M.Assessing model fit by cross-validation[J].J Chem Inf Comput Sci,2003,43(2):579-586.
[16]Wei Dongbin,Zhang Aiqian,Wu Chunde,et al.Progressive study and robustness test of QSAR model based on quantum chemical parameters for predicting BCF of selected polychlorinated organic compounds[J].Chemosphere,2001,44(6):1421-1428.
[17]唐自强,冯长君.用手性连接性指数预测手性有机酸的保留指数[J].南京理工大学学报,2012,36(2):359-363.
Tang Ziqiang,Feng Changjun.Retention indexes prediction of chiral organic acids using chiral connectivity indices[J].Journal of Nanjing University of Science and Technology,2012,36(2):359-363.
[18]李鸣建,陈艳,冯长君.马来酸酯类化合物结构与抑菌活性密度泛函理论研究[J].南京理工大学学报,2014,38(5):383-392.
Li Mingjian,Chen Yan,Feng Changjun.Structure-antibacterial activity relationship of maleic ether compound by density functional theory[J].Journal of Nanjing University of Science and Technology,2014,38(5):383-392.

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Last Update: 2017-06-30