Exploring 1,3,4-Oxadiazole derivatives of 3,4-Dihydroxyphenylacetic acid as potent α-glucosidase inhibitors: Synthesis, structure-activity relationship, molecular docking, and DFT studies
文献类型：期刊论文
| 作者 | Khan, Hammad1; Jan, Faheem2; Aqsa1; Ullah, Qudrat1; Alasmari, Abdullah F.3; Alasmari, Fawaz3; Khan, Ajmal4,5; Ullah, Saeed4; Alam, Aftab6; Al-Harrasi, Ahmed4 |
| 刊名 | JOURNAL OF MOLECULAR STRUCTURE
 |
| 出版日期 | 2025-04-15 |
| 卷号 | 1327页码:11 |
| 关键词 | Oxadiazole & Acy 3,4-dihydroxyphenylacetic acid Spectroscopy Molecular docking and DFT -glucosidase |
| ISSN号 | 0022-2860 |
| DOI | 10.1016/j.molstruc.2024.141211 |
| 通讯作者 | Al-Harrasi, Ahmed(aharrasi@unizwa.edu.om) ; Khan, Momin(mominkhan@awkum.edu.pk) ; Ali, Shaukat(drshaukatali@uop.edu.pk) |
| 英文摘要 | The current work aims to synthesize some new 1,3,4-oxadiazole derivatives bearing 3,4-dihydroxyphenyl acetic acid scaffold as a novel class of alpha-glucosidase inhibitors. A series of novel 1,3,4-oxadiazole derivatives (1-10) of 3,4-dihydroxyphenylacetic acid were synthesized in a series of multi-step reactions. All the synthesized compounds were obtained in good yields (70-85 %), and their structures were determined using 1H-NMR, 13C-NMR and HR-ESI-MS spectroscopy. All derivatives showed excellent to moderate alpha-glucosidase inhibition. Specifically compounds, 2 (IC50 = 17.24 +/- 0.49 mu M), 7 (IC50 = 18.10 +/- 0.72 mu M), 3 (IC50 = 19.34 +/- 0.45 mu M), 5 (IC50 = 20.38 +/- 0.74 mu M), 6 (IC50 = 22.59 +/- 0.74 mu M), 9 (IC50 = 23.18 +/- 1.10 mu M), 4 (IC50 = 24.10 +/- 0.59 mu M), and 1 (IC50 = 25.62 +/- 0.69 mu M) exhibited outstanding inhibition compared to the standard acarbose (IC50 = 873.34 +/- 1.67 mu M). The novelty of this work lies in the effective derivation of 1,3,4-oxadiazoles, posing a new support for alpha-glucosidase inhibitors with encouraging activity. Furthermore, the docking study was carried out to find out the interactions between the active site of the enzyme and the synthesized compounds. Density functional theory (DFT) calculations at B3LYP/6-311++G(d,p) were utilized to ensure the structure stability. Reduced density gradient (RDG) and DFT-D3 methods were used to account for intramolecular interaction. Additionally, the chemical nature of all the compounds was identified using the TD-DFT at the CAM-B3LYP/ 6-311++G(d,p) method. The results of this work highlight the potential of these compounds as powerful candidates for further development of current alpha-glucosidase inhibitors. |
| 资助项目 | King Saud University, and Riyadh, Saudi Arabia[RSP2025R335] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001420289000001 |
| 出版者 | ELSEVIER |
| 资助机构 | King Saud University, and Riyadh, Saudi Arabia |
| 源URL |  |
| 专题 | 金属研究所_中国科学院金属研究所 |
| 通讯作者 | Al-Harrasi, Ahmed; Khan, Momin; Ali, Shaukat |
| 作者单位 | 1.Univ Peshawar, Inst Chem Sci, Organ Synth & Catalysis Res Lab, Peshawar 25120, Khyber Pakhtunk, Pakistan 2.Chinese Acad Sci, Inst Met Res, Shenyang Natl Lab Mat Sci, Shenyang 110016, Liaoning, Peoples R China 3.King Saud Univ, Coll Pharm, Dept Pharmacol & Toxicol, Riyadh 11451, Saudi Arabia 4.Univ Nizwa, Nat & Med Sci Res Ctr, POB 33, Nizwa 616, Oman 5.Korea Univ, Coll Engn, Dept Chem & Biol Engn, Seoul 02841, South Korea 6.Univ Malakand, Dept Chem, Chakdara 18800, Lower Dir, Pakistan 7.Abdul Wali Khan Univ, Dept Chem, Mardan 23200, Pakistan |
| 推荐引用方式 GB/T 7714 | Khan, Hammad,Jan, Faheem,Aqsa,et al. Exploring 1,3,4-Oxadiazole derivatives of 3,4-Dihydroxyphenylacetic acid as potent α-glucosidase inhibitors: Synthesis, structure-activity relationship, molecular docking, and DFT studies[J]. JOURNAL OF MOLECULAR STRUCTURE,2025,1327:11. |
| APA | Khan, Hammad.,Jan, Faheem.,Aqsa.,Ullah, Qudrat.,Alasmari, Abdullah F..,...&Ali, Shaukat.(2025).Exploring 1,3,4-Oxadiazole derivatives of 3,4-Dihydroxyphenylacetic acid as potent α-glucosidase inhibitors: Synthesis, structure-activity relationship, molecular docking, and DFT studies.JOURNAL OF MOLECULAR STRUCTURE,1327,11. |
| MLA | Khan, Hammad,et al."Exploring 1,3,4-Oxadiazole derivatives of 3,4-Dihydroxyphenylacetic acid as potent α-glucosidase inhibitors: Synthesis, structure-activity relationship, molecular docking, and DFT studies".JOURNAL OF MOLECULAR STRUCTURE 1327(2025):11. |
入库方式： OAI收割
来源：金属研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。