Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives
文献类型：期刊论文
| 作者 | Li, Yingjun2; Liu, Xuejie2; Liu, Jihong3; Gao, Lixin1; Jin, Kun4; Sheng, Li1; Yang, Hongjing2; Lin, Ledi2; Li, Jia1
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| 刊名 | CHINESE JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2020-02-25 |
| 卷号 | 40期号:2页码:478-488 |
| 关键词 | carbohydrazone carbazole synthesis PTP1B inhibitor molecular docking DFT calculations |
| ISSN号 | 0253-2786 |
| DOI | 10.6023/cjoc201907043 |
| 通讯作者 | Li, Yingjun(chemlab.lnnu@163.com) ; Li, Jia(jli@simm.ac.cn) |
| 英文摘要 | A series of novel carbazole-based mono-/bis-carbohydrazone derivatives 3 and 4 were synthesized. Their structures were characterized by H-1 NMR, C-13 NMR, IR spectra and elemental analysis. The inhibitory activities of all synthesized compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated, and the structure-activity relationship was discussed. The results indicated that most of the compounds had good inhibitory activity against PTPIB, and 1,5-bis[(9-butyl-3-carbazolypmethylene]carbohydrazone (4c) showed the highest inhibitory activity against PTP1B with IC50 =(4.81 +/- 0.41) mu mol/L and the activity was higher than that of the control drug oleanolic acid. Molecular docking and density functional theory (DFT) calculations of 3f and 4c were carried out. The results of molecular docking indicated that l-[(9-heptyl-3-carbazolyl)methylene]carbohydrazone (3t) and 4c bind to an active site of PTP1B enzyme formed by the helices alpha 3 and alpha 6, and formed a stable complex respectively with PTPIB enzyme by hydrogen bonds, polar, hydrophobic and pi-pi interactions. |
| WOS关键词 | ANTICANCER ; COMPLEXES ; ANTIBACTERIAL ; ANTIOXIDANT ; THIOCARBOHYDRAZONE ; CR(III) ; FE(III) ; MN(II) |
| 资助项目 | Natural Science Foundation of Liaoning Province[20102126] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000522786900022 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/280789]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Li, Yingjun; Li, Jia |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China 2.Liaoning Normal Univ, Coll Chem & Chem Engn, Dalian 116029, Peoples R China 3.Dalian Univ Technol, Chem Anal & Inspect Ctr, Dalian 116023, Peoples R China 4.Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Yingjun,Liu, Xuejie,Liu, Jihong,et al. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2020,40(2):478-488. |
| APA | Li, Yingjun.,Liu, Xuejie.,Liu, Jihong.,Gao, Lixin.,Jin, Kun.,...&Li, Jia.(2020).Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives.CHINESE JOURNAL OF ORGANIC CHEMISTRY,40(2),478-488. |
| MLA | Li, Yingjun,et al."Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives".CHINESE JOURNAL OF ORGANIC CHEMISTRY 40.2(2020):478-488. |
入库方式： OAI收割
来源：上海药物研究所
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