Exploring the synthesis, structure, spectroscopy and biological activities of novel 4-benzylidene-1-(2-(2,4-dichloro phenyl)acetyl) thiosemicarbazide derivatives: An integrated experimental and theoretical investigation

doi:10.1016/j.jsps.2023.101874

IMR OpenIR

	Exploring the synthesis, structure, spectroscopy and biological activities of novel 4-benzylidene-1-(2-(2,4-dichloro phenyl)acetyl) thiosemicarbazide derivatives: An integrated experimental and theoretical investigation
	Waheed, Mahnoor 1; Idris, Sana 1; Jan, Faheem 2; Alam, Aftab 3,4; Ibrahim, Muhammad 1; Alasmari, Abdullah F.5; Alharbi, Metab 5; Alasmari, Fawaz 5; Khan, Momin 1
通讯作者	Ibrahim, Muhammad(dribrahim@awkum.edu.pk) ; Khan, Momin(mominkhan@awkum.edu.pk)
	2023-12-01
发表期刊	SAUDI PHARMACEUTICAL JOURNAL
ISSN	1319-0164
卷号	31 期号:12 页码:13
摘要	Background: Novel alpha-amylase inhibitors play a crucial role in managing diabetes and obesity, contributing to improved public health by addressing these challenging and prevalent conditions. Moreover, the synthesis of anti-oxidant agents is essential due to their potential in combating oxidative stress-related diseases and promoting overall health.Objective: Synthesis of thoisemicarbazone derivatives of 2,4-dichlorophenyl acetic acid and to screened them for their biological activities.Method: Thiosemicarbazone derivatives (4-13) were synthesized by refluxing 2,4-dichlorophenyl acetic acid with sulfuric acid in ethanol to get the ester (2), which was further refluxed with thiosemicarbazide to get compound (3). Finally, different aromatic aldehydes were refluxed with compound (3) in ethanol in catalytic amount of acetic acid to obtained the final products (4-13). Using modern spectroscopic techniques including HR-ESI-MS, C-13-, and H-1 NMR, the structures of the created derivatives were confirmed.Results: The synthesized derivatives showed excellent to good inhibitory activity in the range of IC50 values of 4.95 +/- 0.44 to 69.71 +/- 0.05 mu M against alpha-amylase enzyme when compared to standard drug acarbose (IC50 = 21.55 +/- 1.31 mu M). In case of iron chelating activity, these products showed potent activity better than standard EDTA (IC50 = 66.43 +/- 1.07 mu M) in the range of IC50 values of 22.43 +/- 2.09 to 61.21 +/- 2.83 mu M. However, the obtained products also show excellent to good activity in the range of IC50 values of 28.30 +/- 1.17 to 64.66 +/- 2.43 mu M against hydroxyl radical scavenging activity when compared with standard vitamin C (IC50 = 60.51 +/- 1.02 mu M). DFT used to calculate different reactivity factors including ionization potential, electronegativity, electron affinity, chemical softness, and chemical hardness were calculated using frontier molecular orbital (FMO) computations. The molecular docking studies for the synthesized derivatives with alpha-amylase were carried out using the AutoDock Vina to understand the binding affinities with active sites of the protein.
关键词	Thiosemicarbazone alpha-amylase inhibition Anti-oxidant NMR spectroscopy Structure activity relationship DFT Molecular docking
资助者	King Saud University, Riyadh, Saudi Arabia
DOI	10.1016/j.jsps.2023.101874
收录类别	SCI
语种	英语
资助项目	King Saud University, Riyadh, Saudi Arabia[RSP2023R235]
WOS研究方向	Pharmacology & Pharmacy
WOS类目	Pharmacology & Pharmacy
WOS记录号	WOS:001131518600001
出版者	ELSEVIER
引用统计	被引频次：32[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.imr.ac.cn/handle/321006/183083
专题	中国科学院金属研究所
通讯作者	Ibrahim, Muhammad; Khan, Momin
作者单位	1.Abdul Wali Khan Univ, Dept Chem, Mardan 23200, Pakistan 2.Chinese Acad Sci, Inst Met Res, Shenyang Natl Lab Mat Sci, Shenyang 110016, Liaoning, Peoples R China 3.Univ Malakand, Dept Chem, Chakdara 18800, Pakistan 4.Abdul Wali Khan Univ, Dept Biochem, Mardan 23200, Pakistan 5.King Saud Univ, Coll Pharm, Dept Pharmacol & Toxicol, Riyadh 11451, Saudi Arabia
推荐引用方式 GB/T 7714	Waheed, Mahnoor,Idris, Sana,Jan, Faheem,et al. Exploring the synthesis, structure, spectroscopy and biological activities of novel 4-benzylidene-1-(2-(2,4-dichloro phenyl)acetyl) thiosemicarbazide derivatives: An integrated experimental and theoretical investigation[J]. SAUDI PHARMACEUTICAL JOURNAL,2023,31(12):13.
APA	Waheed, Mahnoor.,Idris, Sana.,Jan, Faheem.,Alam, Aftab.,Ibrahim, Muhammad.,...&Khan, Momin.(2023).Exploring the synthesis, structure, spectroscopy and biological activities of novel 4-benzylidene-1-(2-(2,4-dichloro phenyl)acetyl) thiosemicarbazide derivatives: An integrated experimental and theoretical investigation.SAUDI PHARMACEUTICAL JOURNAL,31(12),13.
MLA	Waheed, Mahnoor,et al."Exploring the synthesis, structure, spectroscopy and biological activities of novel 4-benzylidene-1-(2-(2,4-dichloro phenyl)acetyl) thiosemicarbazide derivatives: An integrated experimental and theoretical investigation".SAUDI PHARMACEUTICAL JOURNAL 31.12(2023):13.