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2-肼基-4-噻唑烷酮杂化物的一种新合成路线、α-葡萄糖苷酶抑制活性评估及分子模拟见解

A new route to the synthesis of 2-hydrazolyl-4-thiazolidinone hybrids, evaluation of α-glucosidase inhibitory activity and molecular modeling insights.

作者信息

Sepehri Saghi, Farhadi Ghazaleh, Maghbul Maryam, Nasiri Farough, Faramarzi Mohammad Ali, Mahnam Karim, Mojtabavi Somayeh, Mahdavi Mohammad, Moharrami Oranj Zhaleh

机构信息

Pharmaceutical Sciences Research Center, Ardabil University of Medical Sciences, Ardabil, Iran.

Department of Medicinal Chemistry, School of Pharmacy, Ardabil University of Medical Sciences, Ardabil, Iran.

出版信息

Heliyon. 2024 Aug 18;10(16):e36408. doi: 10.1016/j.heliyon.2024.e36408. eCollection 2024 Aug 30.

DOI:10.1016/j.heliyon.2024.e36408
PMID:39247345
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11380029/
Abstract

One of the multifactorial worldwide health syndromes is diabetes mellitus which is increasing at a disturbing rate. The inhibition of α-glucosidase, an enzyme that catalyzes starch hydrolysis in the intestine, is one helpful therapeutic approach for controlling hyperglycemia related to type-2 diabetes. To discover α-glucosidase inhibitors, some 2-hydrazolyl-4-thiazolidinone hybrids () were synthesized from new one-pot reaction procedures. Next, their chemical structures were confirmed by H NMR, C NMR, and FT-IR spectra, and elemental analysis technique. Then, the α-glucosidase inhibitory activity of the titled compounds was evaluated. Among them, derivatives and revealed the highest activity against α-glucosidase compared to acarbose as a drug. Enzyme kinetic studies of the most active derivative () indicated a competitive inhibition. Finally, molecular modeling studies were accomplished to describe vital interactions of the most potent compounds ( and ) with the α-glucosidase enzyme.

摘要

糖尿病是全球范围内多因素导致的健康综合征之一，其发病率正以惊人的速度上升。抑制α-葡萄糖苷酶（一种在肠道中催化淀粉水解的酶）是控制2型糖尿病相关高血糖的一种有效治疗方法。为了发现α-葡萄糖苷酶抑制剂，通过新的一锅法反应程序合成了一些2-肼基-4-噻唑烷酮杂化物（）。接下来，通过氢核磁共振（H NMR）、碳核磁共振（C NMR）、傅里叶变换红外光谱（FT-IR）以及元素分析技术确定了它们的化学结构。然后，评估了标题化合物的α-葡萄糖苷酶抑制活性。其中，与作为药物的阿卡波糖相比，衍生物和对α-葡萄糖苷酶显示出最高活性。对活性最高的衍生物（）进行的酶动力学研究表明其为竞争性抑制。最后，进行了分子模拟研究以描述最有效化合物（和）与α-葡萄糖苷酶的重要相互作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/932482222f31/gr13.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/d2981fba6d6f/ga1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/5b4feb265fe3/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/22d28c0b58be/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/fa481e59053b/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/fb70949a4f13/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/19729eabb85d/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/bb56221c10b4/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/cdadae15e573/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/720c98982f81/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/b70d805e15d6/gr6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/13c4c15dfde9/gr7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/987ec0e58e4e/gr8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/3ff8814e52e5/gr9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/29a42a436520/gr10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/652eabf02aad/gr11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/4979e67bece8/gr12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b201/11380029/932482222f31/gr13.jpg

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