3-Substituted-2-oxindole derivatives: Design, synthesis and their anti-tuberculosis and radical scavenging dual-action studies

被引:15
作者
Hublikar, Mahesh [1 ]
Kadu, Vikas [1 ]
Raut, Dattatraya [1 ]
Shirame, Sachin [1 ]
Anbarasu, Sivaraj [2 ]
Al-Muhanna, Muhanna K. [3 ]
Makam, Parameshwar [4 ,5 ]
Bhosale, Raghunath [1 ]
机构
[1] Solapur Univ, Sch Chem Sci, Organ Chem Res Lab, Solapur 413255, Maharashtra, India
[2] Sathyabama Inst Sci & Technol, Ctr Drug Discovery & Dev, Col Dr Jeppiaar Res Pk,Rajiv Gandhi Rd, Chennai 600119, Tamil Nadu, India
[3] King Abdulaziz City Sci & Technol KACST, Mat Sci Res Inst, Riyadh 11442, Saudi Arabia
[4] Lovely Profess Univ, Div Res & Dev, Adv Res Grp, Chem Sci Res Grp, Phagwara 144411, India
[5] IDA, Dr Param Labs, Phase 1, Hyderabad 500051, Telangana, India
关键词
Oxindole derivatives; Drug-like molecule; Anti-oxidant; Anti-tuberculosis; Dual-active molecules; IN-VITRO; MOLECULAR-PROPERTIES; PERMEABILITY; ANTIMYCOBACTERIAL; SOLUBILITY; INHIBITOR; EFFICIENT; OXINDOLE; EXTRACT; POTENT;
D O I
10.1016/j.molstruc.2022.132903
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Despite the fact that the oxindole has long been thought to be the best structural scaffold, research shows that oxindole derivatives are being studied the least against tuberculosis (TB), a historically airborne illness. The present research focuses on the development of 3-substituted-2-oxindole derivatives with a combination of structural and functional alterations in order to create dual-active new chemical entities with anti-TB, anti-oxidant, and radical-scavenging properties. The physicochemical properties of these compounds are in line with the theories of Lipinski, Veeber, and Leeson. SWISSADME was used to assess the drug-like molecular nature and pharmacokinetics features. Multistep synthetic procedures were used to synthesise the chemicals. Based on in vitro anti-TB and radical scavenging property analyses, the synthesised 3-substituted-2-oxindole derivatives were confirmed as dual-active compounds. The synthesised 3-substituted-2-oxindole derivatives were confirmed to possess the dual therapeutics action. The discovery of radical scavengers 4d, 4a, 4c, 3d, 3c, 3f, 3e, 3h, 3g, and 3j that are more potent than Ascorbic acid, the standard. The molecules, 3c, 3j, 3b, and 4b have exhibited moderate to active anti TB properties with a % reduction values of 46.42%, 40.89%, 39.76% and 39.32%, respectively. The findings suggest that fine-tuning molecules might result in compounds with better anti-TB and radical-scavenging properties.(c) 2022 Elsevier B.V. All rights reserved.
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页数:11
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