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<p>A comprehensive structural, thermodynamic, vibrational, and electronic investigation of the <i>s-cis</i> and <i>s-trans</i> conformers of 4-fluorocinnamic acid (4FCA) and 4-methoxycinnamic acid (4MCA) has been carried out using the DFT/B3LYP method in conjunction with FTIR, FT–Raman, FTNMR, and natural bond orbital (NBO) analyses. Conformational stability follows the order I &lt; II &lt; III for both molecules. Bond length comparison reveals shorter C–F bonds in 4FCA conformers compared to fluorobenzene, while 4MCA exhibits characteristic C–OCH₃ and O–CH₃ bond lengths consistent with its structural features. Electron density and electrostatic potential mapping highlight distinct charge distributions in the conformers, while dipole moment calculations confirm higher polarity in 4MCA relative to 4FCA. Frontier molecular orbital analysis shows a larger HOMO–LUMO gap for 4FCA, indicating its greater hardness compared to 4MCA. Strong intramolecular charge transfer interactions, particularly <i>n</i>O → π*CO stabilizations, are evident in both molecules with stabilization energies exceeding 32&#xa0;kcal mol⁻¹. NMR chemical shifts further support delocalization effects, especially in = C–H protons. Fukui function–based reactivity descriptors reveal site selectivity for nucleophilic and electrophilic attacks, with C1 emerging as the most reactive site in both compounds. These combined experimental and theoretical results provide valuable insights into the structural preferences, electronic features, and reactivity patterns of 4FCA and 4MCA conformers. The simulations performed by the Protein-Ligand Interaction Analysis indicated successful binding capabilities of 4FCA and 4MCA to Human Estrogen Receptor Alpha, and it might be used as an anticancer agent. Its pharmacokinetic and drug-likeness were also supported by ADMET predictions. The findings highlight the therapeutic importance of 4FCA and 4MCA present a basis on which the drug will be used in pharmaceutical methods in the future.</p>

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Comprehensive quantum-chemical, spectroscopic, topological, and molecular docking investigation of 4FCA and 4MCA as potential anticancer agents targeting human estrogen receptor alpha

  • 期刊论文

  • 发表日期：

    2026年3月5日

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  • Remya Punnyamurthy,
  • Nekaa Nithya Sre Karuppanan Ayyappan Venkatachalapathy,
  • Jayavarthanan Toulasy,
  • Sivaranjani Tamilmani,
  • Kumaran Manogaran

摘要

A comprehensive structural, thermodynamic, vibrational, and electronic investigation of the s-cis and s-trans conformers of 4-fluorocinnamic acid (4FCA) and 4-methoxycinnamic acid (4MCA) has been carried out using the DFT/B3LYP method in conjunction with FTIR, FT–Raman, FTNMR, and natural bond orbital (NBO) analyses. Conformational stability follows the order I < II < III for both molecules. Bond length comparison reveals shorter C–F bonds in 4FCA conformers compared to fluorobenzene, while 4MCA exhibits characteristic C–OCH₃ and O–CH₃ bond lengths consistent with its structural features. Electron density and electrostatic potential mapping highlight distinct charge distributions in the conformers, while dipole moment calculations confirm higher polarity in 4MCA relative to 4FCA. Frontier molecular orbital analysis shows a larger HOMO–LUMO gap for 4FCA, indicating its greater hardness compared to 4MCA. Strong intramolecular charge transfer interactions, particularly nO → π*CO stabilizations, are evident in both molecules with stabilization energies exceeding 32 kcal mol⁻¹. NMR chemical shifts further support delocalization effects, especially in = C–H protons. Fukui function–based reactivity descriptors reveal site selectivity for nucleophilic and electrophilic attacks, with C1 emerging as the most reactive site in both compounds. These combined experimental and theoretical results provide valuable insights into the structural preferences, electronic features, and reactivity patterns of 4FCA and 4MCA conformers. The simulations performed by the Protein-Ligand Interaction Analysis indicated successful binding capabilities of 4FCA and 4MCA to Human Estrogen Receptor Alpha, and it might be used as an anticancer agent. Its pharmacokinetic and drug-likeness were also supported by ADMET predictions. The findings highlight the therapeutic importance of 4FCA and 4MCA present a basis on which the drug will be used in pharmaceutical methods in the future.