Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity
文献类型：期刊论文
| 作者 | Li Yingjun3; Zhao Yue3; Jin Kun1; Gao Lixin2; Sheng Li2; Liu Xuejie3; Yang Hongjing3; Lin Ledi3; Li Jia2
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| 刊名 | CHINESE JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2019-09-01 |
| 卷号 | 39期号:9页码:2599-2608 |
| 关键词 | 1,3,4-thiadiazolamide carbazole benzimidazole synthesis PTP1B inhibitor molecular docking density functional theory (DFT) study |
| ISSN号 | 0253-2786 |
| DOI | 10.6023/cjoc201901013 |
| 通讯作者 | Li Yingjun(chemlab.lnnu@163.com) ; Li Jia(jli@simm.ac.cn) |
| 英文摘要 | A series of novel 2,5-disubstituted-1,3,4-thiadiazolamide derivatives containing carbazole/benzimidazole moity were synthesized. Their structures were characterized by IR, H-1 NMR, C-13 NMR spectra and elemental analysis. All synthesized target compounds were evaluated for the inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and T-cell protein tyrosine phosphatase (TCPTP). The structure-activity relationship was discussed. The results showed that most of compounds had good inhibitory activity against PTP1B over the highly homologous TCPTP, and 2-(9-carbazolylmethylene)-5-(3-chlorobenzoylamino)-1,3,4-thiadiazole (5c) displayed the highest inhibitory activity against PTP1B [IC50=(2.43 +/- 0.43) mu g/mL]. The inhibitory activities of 2-(9- carbazolylmethylene)-5-(4-methylbenzoylamino)-1,3,4-thiadiazole (5b) and 5c against PTP1B were higher than that of positive control oleanolic acid. Molecular docking and density functional theory (DFT) calculations of the target compound 5c were performed. The docking result showed that compound 5c and PTP1B enzyme formed a stable complex by hydrogen bonds, hydrophobic and pi-pi interactions. |
| WOS关键词 | PROTEIN-TYROSINE PHOSPHATASES ; BENZIMIDAZOLE DERIVATIVES ; BIOLOGICAL EVALUATION ; PTP1B INHIBITORS ; DISCOVERY ; 1,3,4-THIADIAZOLES ; ANTIOXIDANT ; THIADIAZOLE ; SELECTIVITY ; POTENT |
| 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:000489272700025 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/282619]  |
| 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.Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China 2.Chinese Acad Sci, Natl Ctr Drug Screening, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 3.Liaoning Normal Univ, Coll Chem & Chem Engn, Dalian 116029, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li Yingjun,Zhao Yue,Jin Kun,et al. Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2019,39(9):2599-2608. |
| APA | Li Yingjun.,Zhao Yue.,Jin Kun.,Gao Lixin.,Sheng Li.,...&Li Jia.(2019).Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity.CHINESE JOURNAL OF ORGANIC CHEMISTRY,39(9),2599-2608. |
| MLA | Li Yingjun,et al."Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity".CHINESE JOURNAL OF ORGANIC CHEMISTRY 39.9(2019):2599-2608. |
入库方式： OAI收割
来源：上海药物研究所
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