Experimental and theoretical study on the structure and electronic spectra of imiquimod and its synthetic intermediates
文献类型：期刊论文
| 作者 | Zhao, Bo; Rong, Yu-Zhi; Huang, Xiao-Hua; Shen, Jing-Shan
|
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
 |
| 出版日期 | 2007-09-01 |
| 卷号 | 17期号:17页码:4942-4946 |
| 关键词 | imiquimod density functional theory electronic absorption spectra fluorescence emission spectra |
| ISSN号 | 0960-894X |
| DOI | 10.1016/j.bmcl.2007.06.020 |
| 文献子类 | Article |
| 英文摘要 | Crystal structure of the imiquimod has been determined by single crystal X-ray analysis, imiquimod crystallizes in orthorhombic space group P2(1)2(1)2(1) and the molecules are linked along the c axis by the strong N-H... N hydrogen bonds. A density functional theory (DFT) study on the electronic properties of imiquimod and its synthetic intermediates has been performed at B3LYP/ 6-31G* level, while taking solvent effects into account. Both the single configuration interaction (CIS) method and the time-dependent DFT (TDDFT) approaches have been used to calculate the electronic absorption spectra, and there is a good agreement between the calculated and experimental UV-visible absorption spectra. The fluorescence emission spectra of these three compounds in solution have also been measured, the relatively low fluorescence intensity is attributed to a chlorine-modulated heavy atom effect that enhances intersystem crossing between excited singlet and triplet states, and the relatively high fluorescence intensity of imiquimod results from an extended pi-conjugated system which enhances S, So radiant transition. (C) 2007 Elsevier Ltd. All rights reserved. |
| WOS关键词 | DENSITY-FUNCTIONAL THEORY ; BASAL-CELL CARCINOMA ; 5-PERCENT CREAM ; DOUBLE-BLIND ; 8-HYDROXYADENINES ; 2-PHASE-III |
| WOS研究方向 | Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000249151700044 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/273155]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Zhao, Bo |
| 作者单位 | 1.Nanjing Normal Univ, Coll Chem & Environm Sci, Nanjing 210097, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, SIBS, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhao, Bo,Rong, Yu-Zhi,Huang, Xiao-Hua,et al. Experimental and theoretical study on the structure and electronic spectra of imiquimod and its synthetic intermediates[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2007,17(17):4942-4946. |
| APA | Zhao, Bo,Rong, Yu-Zhi,Huang, Xiao-Hua,&Shen, Jing-Shan.(2007).Experimental and theoretical study on the structure and electronic spectra of imiquimod and its synthetic intermediates.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,17(17),4942-4946. |
| MLA | Zhao, Bo,et al."Experimental and theoretical study on the structure and electronic spectra of imiquimod and its synthetic intermediates".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 17.17(2007):4942-4946. |
入库方式： OAI收割
来源：上海药物研究所
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