A Greener synthesis, spectroscopical relationships, molecular docking analysis, antimicrobial, antimalarial activities of aryl E-imines and X-ray crystal structure of (E)-N-(4-nitrobenzylidene)-2-(trifluoromethyl)aniline

Authors

  • Dr. Thirunarayanan G Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India https://orcid.org/0000-0001-9304-726X
  • V Usha Department of Chemistry, University College of Engineering Panruti, Panruti 607 106, Tamil Nadu, India
  • K Ranganathan Department of Chemistry, P. T. Lee Chengalvaraya Naickar College of Engineering & Technology, Kanchipuram 631 502, Tamil Nadu, India
  • B Krishnakumar Saveetha School of Engineering, Saveetha Institute of Medical and Technical Sciences (SIMATS), Chennai 602 105, India, ; Department of Civil Engineering, Yeungnam University, Gyeongsan 38541, Republic of Korea, ; Center for Research Impacr and Outcome, Chitkara University Institute of Engineering and Technology, Chitkara University, Rajpura 140 401, Punjab, India
  • D Govindarajan Department of Physics, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India
  • J Divya Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India, ; Department of Chemistry, Indra Ganesan College of Engineering College, College, Manikandam, Tiruchirappalli 620 012, Tamilnadu, India
  • P Sudha Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India
  • S Balasundari Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India
  • I Muthuvel Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India, ; Department of Chemistry, M. R. Government Arts College, Mannargudi 614 001, Tamil Nadu, India
  • P Mayavel Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India, ; Department of Chemistry, Government Arts College, Ariyalur 621 713, Tamil Nadu, India (Affiliated to Bharathidasan University, Tiruchirppalli 620 024, Tamil Nadu, India
  • P Gayathri Department of Chemistry, Annamalai University, Annamalinagar 608 002, Tamil Nadu, India
  • K Devika Department of Chemistry, Thiru. Vi. Ka. Government Arts College, Thiruvarur 610 003, Tamil Nadu, India. (Affiliated to Bharathidasan University, Tiruchirppalli 620 024, Tamil Nadu, India)

DOI:

https://doi.org/10.56042/ijc.v65i4.26287

Abstract

Three series of E-imines such as (E)-N-(substituted benzylidene)-2,3-dihydrobenzo(b)[1,4]-dioxin-6-amines,  (E)-[4-(substituted benzylideneamino) phenyl] (phenyl) methanones and (E)-N-(substituted benzylidene)-2-(trifluoromethyl)anilines were synthesized by sulfated fly-ash:SnO2 catalyst assisted condensation of  2,3-dihydro(b)[1,4]dioxin-6-amine, 4-benzoylaniline, 2-trifluromethylaniline and substituted benzaldehydes under microwave irradiation conditions. This condensation gave more than 70% yields. Physicochemical constants, elemental analysis, and spectroscopical information were applied for the characterization of synthesized E-imines.  The X-ray single crystal structure of (E)-N-(4-nitrobenzylidene)-2-(trifluoromethyl) aniline (27) was established.  Specific spectroscopical wave numericals of the imines were applied for QSAR linear statistical investigations. Based on the outcomes of linear QSAR computations, the influence of auxiliaries on specified spectroscopical data was investigated. Resonance & inductive properties of the auxiliaries yield satisfactory correlations (r > 0.900).  In molecular-docking analysis, the E-imines 4, 7, 10, 11, 13, 16, 17, and 22 show high protein-ligand interaction binding energy.  The imines 5-7 and 10 show good anti-bacterial actions in contrast to S. aureus, E. coli, and P. aeruginosa strains. In the serial dilution method, all compounds are active against their antibacterial strains. The imines 2-9, 24, and 26 were active with MICs of 9.5-16.5 against A. niger microbes. Imines 4, 5, 14-16, and 22 exhibit good antimalarial activities against P. falciparum strain.

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Published

2026-05-12

Issue

Vol. 65 No. 4 (2026): Indian Journal of Chemistry-(IJC)

Section

Papers

How to Cite

A Greener synthesis, spectroscopical relationships, molecular docking analysis, antimicrobial, antimalarial activities of aryl E-imines and X-ray crystal structure of (E)-N-(4-nitrobenzylidene)-2-(trifluoromethyl)aniline. (2026). Indian Journal of Chemistry (IJC), 65(4), 348-367. https://doi.org/10.56042/ijc.v65i4.26287

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