Design and Synthesis of Novel Bio-MOF UTSA-16 (Zn) Catalyst for One-Pot Synthesis of 3,3-Di(indolyl)indolin-2-ones: Their Molecular Docking, Anti-Microbial, and Anti-Oxidant Evaluation

IF 3.7 2区 化学 Q2 CHEMISTRY, APPLIED
Akshay Gurav, Dipali Kuchekar, Lalit Bhosale, Prasad Swami, Prakash Chavan, Nisha Nerlekar, Padma Dandge, Praful Choudhari, Sneha Rochlani, Sandeep Sankpal, Shankar Hangirgekar
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Abstract

This study explored the catalytic potential of the bio-MOF UTSA-16 (Zn) for the synthesis of novel 3,3-di (indolyl)indolin-2-ones through one-pot reactions between isatins and indoles. The present approach involved water as an eco-friendly solvent, and the hydrothermally synthesized bio-MOF UTSA-16 (Zn) catalyst has been comprehensively characterized by using XRD, SEM, EDX, TG-DTA, FT-IR, and BET analytical techniques. The UTSA-16 (Zn) MOF exhibited catalytic efficiency toward the candidates for 3,3-di (indolyl)indolin-2-one, which were fully characterized using 1H and 13C NMR spectrometry. Furthermore, the catalyst demonstrated excellent reusability and stability, maintaining its catalytic performance across five successive cycles without significant loss of reactivity. Additionally, the in vitro antimicrobial activity of the synthesized 3,3-di (indolyl)indolin-2-one derivatives and reference drugs was evaluated against gram-negative and gram-positive bacteria, specifically Escherichia coli and Staphylococcus aureus. Compounds 3b and 3e consistently demonstrated the most potent antimicrobial activity against E. coli and S. aureus, showing zones of inhibition of 6–7 mm and 15 mm at a concentration of 100 μg/mL. The DPPH assay indicated that Compound 3e exhibited the most significant antioxidant activity, with an IC50 value of 52.34 ± 0.20 μg/mL, reflecting its high efficacy in scavenging DPPH radicals. Moreover, molecular docking studies were conducted on the synthesized compounds, aligning with the in vitro results and supported by a structural activity relationship study. This protocol highlights several key advantages, including green solvent, operational simplicity, short reaction times, reusability, high product yields, and availability of high surface area of the UTSA-16 (Zn) catalyst.

Abstract Image

一锅法合成3,3-二(吲哚基)吲哚-2-酮的新型生物mof UTSA-16 (Zn)催化剂的设计与合成:分子对接、抗菌及抗氧化评价
本研究考察了生物mof UTSA-16 (Zn)在吲哚类化合物与吲哚类化合物之间通过一锅反应合成新型3,3-二(吲哚基)吲哚-2-酮的催化潜力。采用水作为环保溶剂,采用XRD、SEM、EDX、TG-DTA、FT-IR、BET等分析技术对水热合成的生物mof UTSA-16 (Zn)催化剂进行了全面表征。UTSA-16 (Zn) MOF对3,3-二(吲哚基)吲哚-2- 1的候选物表现出催化效率,并用1H和13C NMR对候选物进行了表征。此外,该催化剂表现出优异的可重复使用性和稳定性,在连续5个循环中保持其催化性能,而没有明显的反应性损失。此外,合成的3,3-二(吲哚基)吲哚-2- 1衍生物和参比药物对革兰氏阴性菌和革兰氏阳性菌,特别是大肠杆菌和金黄色葡萄球菌的体外抗菌活性进行了评价。在100 μg/mL浓度下,化合物3b和3e对大肠杆菌和金黄色葡萄球菌的抑制范围分别为6 ~ 7 mm和15 mm。DPPH实验结果表明,化合物3e的抗氧化活性最强,IC50值为52.34±0.20 μg/mL,表明化合物3e具有较强的DPPH清除能力。并对合成的化合物进行了分子对接研究,与体外实验结果一致,并进行了构效关系研究。该方案突出了几个关键优势,包括绿色溶剂,操作简单,反应时间短,可重复使用,产品收率高,以及UTSA-16 (Zn)催化剂的高表面积。
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来源期刊
Applied Organometallic Chemistry
Applied Organometallic Chemistry 化学-无机化学与核化学
CiteScore
7.80
自引率
10.30%
发文量
408
审稿时长
2.2 months
期刊介绍: All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.
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