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Computational study of the substituent effect of halogenated fused-ring heteroaromatics on halogen bonding

文献类型：期刊论文

作者Zhang, Qihua1,2,3; Smalley, Adam4; Zhu, Zhengdan2,3; Xu, Zhijian2,3; Peng, Cheng2,3; Chen, Zhaoqiang2,3; Yao, Guangmin1; Shi, Jiye4; Zhu, Weiliang2,3
刊名JOURNAL OF MOLECULAR MODELING
出版日期2020-09-15
卷号26期号:10页码:12
ISSN号1610-2940
关键词Halogen bonding Fused-ring heteroaromatics Quantum chemistry calculation sigma-hole Electrostatic potential Binding energy
DOI10.1007/s00894-020-04534-x
通讯作者Yao, Guangmin(gyap@mail.hust.edu.cn) ; Zhu, Weiliang(wlzhu@simm.ac.cn)
英文摘要Halogen bonding (XB) has been applied in many fields from crystal engineering to medicinal chemistry. Compared with the well-studied XB of simple halogenated aromatics, little research has been done on the XB of halogenated fused-ring heteroaromatics, a prevalent substructure in organic compounds. With 1H-pyrrolo[3,2-b]pyridines (PPs) as examples of novel fused-ring heteroaromatics with hydrogen bond donor and acceptor and XB donor, the XB formed by the halogenated heteroaromatics was explored in this study. With 4 different substituents, viz., -CH3, -NH2, -F, and -CONH2, at different positions, 339 derivatives of brominated PP (Br-PP) were designed for calculating their electrostatic potential of the sigma-hole of the halogen atom (V-S,V-max) and binding energy with ammonia as XB acceptor (E-int) at M06-2X/6-311++G(d,p) level by PCM model in dichloromethane. The calculatedV(S,max)values ranging from -1.3 to 35.1 kcal/mol and the calculatedE(int)ranging from -0.82 to -2.37 kcal/mol demonstrated that the XB is complicated and highly tunable. Noticeably, the electron-withdrawing substituents, especially at ortho-position, do not always increase the values ofV(S,max), while the electron-donating substituents do not always decreaseV(S,max). Similar results were observed from the calculation on 339 iodinated PPs at M06-2X/6-311++G(d,p) level. The complexity of the XB formed by the halogenated fused ring heteroaromatics indicated a great potential of tuning its strength by different substituents at different positions and revealed a necessity of quantum chemistry calculation for predicting the XB. Graphical abstract
WOS关键词MEDICINAL CHEMISTRY ; DISCOVERY ; ATOMS ; COMPLEXES ; MOIETY ; ENERGY
资助项目National Natural Science Foundation of China[31870717] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002]
WOS研究方向Biochemistry & Molecular Biology ; Biophysics ; Chemistry ; Computer Science
语种英语
出版者SPRINGER
WOS记录号WOS:000573070400001
源URL[http://119.78.100.183/handle/2S10ELR8/291247]  
专题中国科学院上海药物研究所
通讯作者Yao, Guangmin; Zhu, Weiliang
作者单位1.Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Wuhan 430030, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, Shanghai 201203, Peoples R China
4.UCB Pharma, 208 Bath Rd, Slough SL1 3WE, Berks, England
推荐引用方式
GB/T 7714		 Zhang, Qihua,Smalley, Adam,Zhu, Zhengdan,et al. Computational study of the substituent effect of halogenated fused-ring heteroaromatics on halogen bonding[J]. JOURNAL OF MOLECULAR MODELING,2020,26(10):12.
APA Zhang, Qihua.,Smalley, Adam.,Zhu, Zhengdan.,Xu, Zhijian.,Peng, Cheng.,...&Zhu, Weiliang.(2020).Computational study of the substituent effect of halogenated fused-ring heteroaromatics on halogen bonding.JOURNAL OF MOLECULAR MODELING,26(10),12.
MLA Zhang, Qihua,et al."Computational study of the substituent effect of halogenated fused-ring heteroaromatics on halogen bonding".JOURNAL OF MOLECULAR MODELING 26.10(2020):12.

入库方式： OAI收割

来源：上海药物研究所

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