硝基芳烃类含能材料撞击钝度的比较分子力场分析
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摘要
基于比较分子力场分析(CoMFA)方法建立34种硝基芳烃类炸药分子的结构与撞击钝度(DH)的三维定量构效关系(3D-QSAR)。训练集中28个化合物用于建立预测模型,测试集6个化合物作为模型验证。已建立的CoMFA模型的交叉验证系数(Q~2)、非交叉验证系数(R~2)分别为0.432、0.923,说明所建模型具有较强的稳定性和良好的预测能力。该模型中立体场、静电场贡献率依次为37.9%、62.1%,表明影响撞击钝度DH的主要因素是取代基的电荷分布,其次是取代基的空间位阻。所建模型可用于指导该类化合物的设计。
Based on the comparative molecular field analysis( CoMFA) methods,three dimensional quantitative structure-activity relationships( 3D-QSAR) between the molecular structures and their impact dullness( DH) of 34 polynitroaromatic explosive compounds were established.Twenty eight compounds in the training set were served to build the predicting models,and the test set of six compounds were used to validate the models.The coefficients of the cross-validation( Q~2) and non cross-validation( R~2) for CoMFA model established in this study were 0. 432 and 0. 923,respectively.The results showed that the model had strong stability and good predictability.In this model,the contributions of the steric and electrostatic fields were 37. 9% and 62. 1% ,respectively,indicating that the main factor to impact on DHwas the charge distributions of substituted groups,followed by steric hindrance. The 3DQSAR model can be used to guide designing this kind of the compounds.
Based on the comparative molecular field analysis( CoMFA) methods,three dimensional quantitative structure-activity relationships( 3D-QSAR) between the molecular structures and their impact dullness( DH) of 34 polynitroaromatic explosive compounds were established.Twenty eight compounds in the training set were served to build the predicting models,and the test set of six compounds were used to validate the models.The coefficients of the cross-validation( Q~2) and non cross-validation( R~2) for CoMFA model established in this study were 0. 432 and 0. 923,respectively.The results showed that the model had strong stability and good predictability.In this model,the contributions of the steric and electrostatic fields were 37. 9% and 62. 1% ,respectively,indicating that the main factor to impact on DHwas the charge distributions of substituted groups,followed by steric hindrance. The 3DQSAR model can be used to guide designing this kind of the compounds.
引文
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[12]Feng C,Yang W.Linear QSAR regression models for the prediction of bioconcentration factors of chloroanilines in fish by density functional theory[J].Chin J Struct Chem,2014,33(6):830-834.
[13]堵锡华.用新的路径定位指数和神经网络研究多溴联苯醚理化性质[J].化工学报,2014,65(4):1169-1178.
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[15]Zhang K,Michael H A,Liu X.An equation for the prediction of human skin permeability of neutral molecules,ions and ionic species[J].Inter J Pharm Chem Eng Res Des,2017,521(1-2):259-266.
[16]Vijay H M,Devidas T M,Ahmed M A,et al.Optimization of antiproliferative activity of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates:QSAR and Co MFA analyses[J].Eur J Pharm Sci,2015,77(9):230-237.
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[18]Babu S,Sohn H,Madhavan T.Computational analysis of CRTh2 receptor antagonist:aligand-based Co MFA and Co MSIAapproach[J].Comput Biol Chem,2015,56(1):109-121.
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[20]宰小丽,舒茂,张贝娜,等.基于3D-QSAR及分子对接的MPS1抑制剂的构效关系研究[J].化学研究与应用,2016,28(8):1092-1097.
[21]汪斌,常自超,舒茂,等.氰基吡咯烷类FAP抑制剂的分子对接及3D-QSAR研究[J].化学研究与应用,2016,28(7):947-953.
[22]舒远杰,杜军良,黄奕刚,等.芳香族硝基化合物撞击感度的理论研究[J].绵阳师范学院学报,2009,28(8):1-7.
[23]胡松青,米思奇,贾晓林,等.苯并咪唑类缓蚀剂的3DQSAR研究及分子设计[J].高等学校化学学报,2011,32(10):2402-2409.
[24]刘东,章文军,许禄.手性羟酸和氨基酸类化合物的构效关系研究[J].化学学报,2009,67(2):145-150.
[25]杜军良,舒远杰,周阳,等.用分子拓扑参数预估多硝基芳香族化合物的撞击感度[J].火炸药学报,2010,33(6):5-10.
[2]Atalar T,Jungova M,Zeman S.A new view of relationships of the N-N bond dissociation energies of cyclic nitramines partⅡ.Relationships with impact sensitivity[J].J Ener Mater,2009,27(3):200-216.
[3]Besty M R,Samir S,Frank J O.Densityfunctional calculations of bond dissociation energies for NO2scissionin some nitroaromatic molecules[J].J Mole Struc(Theochem),2002,583:69-72.
[4]李疏芬,王进.1,3,5-三硝基苯类化合物的撞击感度与分子拓扑指数[J].推进技术,2000,21(5):69-72.
[5]王开明,程新路,张红,等.硝基苯衍生物的撞击感度与其静电势的关系研究[J].四川师范大学学报(自然科学版),2003,26(5):505-508.
[6]王开明,张红,程新路,等.硝基甲苯类炸药C-NO2键中点的静电势[J].原子与分子物理学报,2003,20(2):266-270.
[7]唐自强,堵锡华,冯长君.呋虫胺衍生物杀虫活性的理论研究[J].化学通报,2014,77(6):545-549.
[8]顾云兰,张淦杰.酚类化合物对梨形四膜虫毒性的构效关系解析[J].化学研究与应用,2016,28(6):810-817.
[9]孙运佳,张荣荣,施宇靖,等.新型苯并噻(噁)唑酮衍生物抑制黄瓜炭疽菌活性的QSAR研究[J].化学研究与应用,2016,28(6):818-823.
[10]李鸣建,陈艳,冯长君.苯甲酰硫脲类化合物生物活性的QSAR模型和结构修饰的理论研究[J].化学研究与应用,2015,27(11):1693-1697.
[11]Zhu H,Guo W,Shen Z,et al.QSAR models for degradation of organic pollutants in ozonation process under acidic condition[J].Chemosphere,2015,119(1):65-71.
[12]Feng C,Yang W.Linear QSAR regression models for the prediction of bioconcentration factors of chloroanilines in fish by density functional theory[J].Chin J Struct Chem,2014,33(6):830-834.
[13]堵锡华.用新的路径定位指数和神经网络研究多溴联苯醚理化性质[J].化工学报,2014,65(4):1169-1178.
[14]Diako G,Zahra E G,Ali E G,et al.Descriptive and predictive models for Henry’s law constant of CO2in ionic liquids:A QSPR study[J].Chem Engin Res Des,2017,120(1):15-25.
[15]Zhang K,Michael H A,Liu X.An equation for the prediction of human skin permeability of neutral molecules,ions and ionic species[J].Inter J Pharm Chem Eng Res Des,2017,521(1-2):259-266.
[16]Vijay H M,Devidas T M,Ahmed M A,et al.Optimization of antiproliferative activity of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates:QSAR and Co MFA analyses[J].Eur J Pharm Sci,2015,77(9):230-237.
[17]Han X,Shi J,Chen T.2D-and 3D-QSBR studies on the relationship between structureand biodegradability of phthalates[J].Chin J Struct Chem,2014,33(8):1109-1116.
[18]Babu S,Sohn H,Madhavan T.Computational analysis of CRTh2 receptor antagonist:aligand-based Co MFA and Co MSIAapproach[J].Comput Biol Chem,2015,56(1):109-121.
[19]李鸣建,冯惠,冯长君,等.取代喹啉类化合物抗菌活性的3D-QSAR研究及分子设计[J].化学通报,2015,78(2):153-157
[20]宰小丽,舒茂,张贝娜,等.基于3D-QSAR及分子对接的MPS1抑制剂的构效关系研究[J].化学研究与应用,2016,28(8):1092-1097.
[21]汪斌,常自超,舒茂,等.氰基吡咯烷类FAP抑制剂的分子对接及3D-QSAR研究[J].化学研究与应用,2016,28(7):947-953.
[22]舒远杰,杜军良,黄奕刚,等.芳香族硝基化合物撞击感度的理论研究[J].绵阳师范学院学报,2009,28(8):1-7.
[23]胡松青,米思奇,贾晓林,等.苯并咪唑类缓蚀剂的3DQSAR研究及分子设计[J].高等学校化学学报,2011,32(10):2402-2409.
[24]刘东,章文军,许禄.手性羟酸和氨基酸类化合物的构效关系研究[J].化学学报,2009,67(2):145-150.
[25]杜军良,舒远杰,周阳,等.用分子拓扑参数预估多硝基芳香族化合物的撞击感度[J].火炸药学报,2010,33(6):5-10.