Comprehensive analysis of hydrazone Schiff bases: Synthesis, structural characterization, DFT studies, molecular docking insights and bioactivity assessment

被引：0
作者：
Tiwari, Ashish Kumar [1 ]
Sk, Vaishnu [2 ]
Narayanan, Mohankumar [3 ]
Garg, Mohit [2 ]
Manoharan, Vishnu Varma [1 ]
Nallasivam, Jothi L. [1 ]
Biju, V. M. [1 ]
机构：
[1] Natl Inst Technol Tiruchirappalli, Dept Chem, Tiruchirappalli 620015, Tamil Nadu, India
[2] Birla Inst Technol & Sci BITS Pilani, Dept Chem Engn, Pilani Campus, Pilani 333031, Rajasthan, India
[3] Bharathidasan Univ, Dept Marine Sci, Marine Pharmacol & Toxicol Lab, Tiruchirappalli 620024, Tamil Nadu, India
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2025年 / 1335卷
关键词：
4-dinitrophenylhydrazine; TGA; DFT; Molecular docking; Swiss ADME; Antibacterial studies; BIOLOGICAL-ACTIVITIES; ANTIOXIDANT; ABSORPTION; INHIBITORS; COMPLEXES; PROTEASE; METALS; INDEX;
D O I：
10.1016/j.molstruc.2025.141905
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：
The four new hydrazone Schiff bases have been synthesized in absolute ethanol at the reflux of 78 degrees C. These hydrazones are named as: (E)-1-(2,4-dinitrophenyl)-2-(2-ethoxy benzylidene) hydrazine(2-EDNPH) (L1), (E)-1(2,4-dinitrophenyl)-2-(4-ethoxy benzylidene) hydrazine(4-EDNPH) (L2), (E)-3-chloro-2-((2-(2,4-dinitrophenyl) hydrazinylidene) methyl) phenol(3-Cl-2-OH-DNPH) (L3) and (E)-1-(2,4-dinitrophenyl)-2-(thiophen-3-ylmethylene) hydrazine (3-Thiophene Carbaldehyde-DNPH) (L4). Spectroscopic and physicochemical techniques were employed to validate these compound's structure, including 1H NMR, 13C NMR spectra, UV-Vis, IR, and melting point. A solubility test is also carried out on all the Schiff bases, indicating that all four ligands are soluble in THF and DMF. The thermal breakdown behavior of all ligands is being examined by thermogravimetric analysis (TGA/DTG) at a heating rate of 10 degrees C min-1 under a nitrogen environment. The crystalline structure of L1 was also investigated in an XtaLAB AFC12 (RINC): Kappa single diffractometer, which included unit cell computation and data collecting. The radioactive photon was created with MoK alpha (lambda = 0.7107 angstrom). In addition, density functional theory (DFT) is utilized to compute the optimized molecular structures, stability, reactivity, and numerous chemical characteristics of the synthesized ligands. The in-silico prediction of ADME features revealed that synthesized compounds gain notable drug-like characteristics. Also, molecular docking was enforced to predict the inhibitory action of the beta-ketoacyl acyl carrier (KAS1) protein of E. Coli (PDB Id: 6TZF) on the examined hydrazones. Finally, all ligands were to assess the anti-bacterial properties against gram-positive (B. subtilis and MRSA) and gram-negative (P. mirabilis and E. coli) infections; only L1 and L2 showed activity against these pathogens.
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页数：17
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共 85 条
  • [1] Qin W., Long S., Panunzio M., Biondi S., Schiff bases: A short survey on an evergreen chemistry tool, Molecules, 18, pp. 12264-12289, (2013)
  • [2] Kargar H., Fallah-Mehrjardi M., Munawar K.S., Metal complexes incorporating tridentate ONO pyridyl hydrazone Schiff base ligands: crystal structure, characterization and applications, Coord. Chem. Rev., 501, (2024)
  • [3] Hussain I., Ullah A., Khan A.U., Khan W.U., Ullah R., Shahat A.A., Naser A.A., Mahmood H.M., Synthesis, characterization and biological activities of hydrazone Schiff base and its novel metals complexes, Sains Malays, 48, pp. 1439-1446, (2019)
  • [4] Riaz M., Jan F., Khan A., Ullah A., Haq H., AlAsmari A.F., Alharbi M., Alasmari F., Khan M., Unraveling the molecular structure, spectroscopic properties, and antioxidant activities of new 2,4-dinitrophenylhydrazone derivatives through a comprehensive investigation, Arabian J. Chem., 16, (2023)
  • [5] Deng X., Mani N.S., Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles from N-arylhydrazones and nitroolefins, J. Org. Chem., 73, pp. 2412-2415, (2008)
  • [6] Gil D.M., Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone, J. Mol. Struct., (2020)
  • [7] Hussain I., Ullah A., Khan A.U., Khan W.U., Ullah R., Shahat A.A., Naser A.A., Mahmood H.M., Synthesis, characterization and biological activities of hydrazone Schiff base and its novel metals complexes, Sains Malays, 48, pp. 1439-1446, (2019)
  • [8] Anitha C., Sumathi S., Tharmaraj P., Sheela C.D., Synthesis, characterization, and biological activity of some transition metal complexes derived from novel hydrazone Azo Schiff base ligand, Int. J. Inorg Chem., 2011, pp. 1-8, (2011)
  • [9] Anoop M.R., Binil P.S., Suma S., Sudarsanakumar M.R., Y S.M., Varghese H.T., Panicker C.Y., Vibrational spectroscopic studies and computational study of ethyl methyl ketone thiosemicarbazone, J. Mol. Struct., 969, pp. 48-54, (2010)
  • [10] Verma G., Marella A., Shaquiquzzaman M., Akhtar M., Ali M.R., Alam M.M., A review exploring biological activities of hydrazones, J. Pharm. Bioallied Sci., 6, pp. 69-80, (2014)
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