Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies
Abstract The compound (2E)-3-(4-Fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one (FIPP) was synthesized via Claisen-Schmidt condensation and fully characterized using FT-IR, 1H and 13C NMR, HRMS, and single-crystal X-ray diffraction. HRMS analysis validated the molecular composition and purity, wh...
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Springer
2025-05-01
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| Series: | Discover Chemistry |
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| Online Access: | https://doi.org/10.1007/s44371-025-00195-y |
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| author | Nutan V. Sadgir Vishnu A. Adole Sunil L. Dhonnar Bapu S. Jagdale Kailas H. Kapadnis Jayesh Pawar |
| author_facet | Nutan V. Sadgir Vishnu A. Adole Sunil L. Dhonnar Bapu S. Jagdale Kailas H. Kapadnis Jayesh Pawar |
| author_sort | Nutan V. Sadgir |
| collection | DOAJ |
| description | Abstract The compound (2E)-3-(4-Fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one (FIPP) was synthesized via Claisen-Schmidt condensation and fully characterized using FT-IR, 1H and 13C NMR, HRMS, and single-crystal X-ray diffraction. HRMS analysis validated the molecular composition and purity, while single-crystal X-ray diffraction revealed that FIPP crystallizes in the orthorhombic system [space group P2(1)2(1)2(1)] with unit cell parameters a = 6.4704 (4) Å, b = 12.9304 (8) Å, c = 16.7181 (11) Å, α = β = γ = 90°, and Z = 4. DFT/B3LYP calculations with a 6–311++G(d,p) basis set showed strong agreement with experimental data, confirming the reliability of the computational approach. Antimicrobial studies demonstrated moderate antibacterial activity against gram-negative (Escherichia coli, Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus, Streptococcus pyogenes) bacteria, as well as moderate antifungal activity against Candida albicans, Aspergillus niger, and Aspergillus clavatus. Docking studies against 4URO (antibacterial target) and 5V5Z (antifungal target) gave docking scores of − 8.1 kcal/mol and − 9.1 kcal/mol, respectively, indicating strong binding interactions through hydrogen bonding, electrostatic, and hydrophobic forces. ADME profiling revealed high gastrointestinal absorption, blood–brain barrier permeability, selective P450 inhibition, and moderate bioavailability, highlighting ’s pharmacokinetic potential. Graphical abstract |
| format | Article |
| id | doaj-art-a6633b70e4d64c06aca04eab82453252 |
| institution | DOAJ |
| issn | 3005-1193 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Springer |
| record_format | Article |
| series | Discover Chemistry |
| spelling | doaj-art-a6633b70e4d64c06aca04eab824532522025-08-20T03:22:08ZengSpringerDiscover Chemistry3005-11932025-05-012111610.1007/s44371-025-00195-ySynthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studiesNutan V. Sadgir0Vishnu A. Adole1Sunil L. Dhonnar2Bapu S. Jagdale3Kailas H. Kapadnis4Jayesh Pawar5Department of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiDepartment of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiDepartment of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiDepartment of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiDepartment of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiDepartment of Chemistry and Research Centre in Chemistry, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune), PanchavatiAbstract The compound (2E)-3-(4-Fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one (FIPP) was synthesized via Claisen-Schmidt condensation and fully characterized using FT-IR, 1H and 13C NMR, HRMS, and single-crystal X-ray diffraction. HRMS analysis validated the molecular composition and purity, while single-crystal X-ray diffraction revealed that FIPP crystallizes in the orthorhombic system [space group P2(1)2(1)2(1)] with unit cell parameters a = 6.4704 (4) Å, b = 12.9304 (8) Å, c = 16.7181 (11) Å, α = β = γ = 90°, and Z = 4. DFT/B3LYP calculations with a 6–311++G(d,p) basis set showed strong agreement with experimental data, confirming the reliability of the computational approach. Antimicrobial studies demonstrated moderate antibacterial activity against gram-negative (Escherichia coli, Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus, Streptococcus pyogenes) bacteria, as well as moderate antifungal activity against Candida albicans, Aspergillus niger, and Aspergillus clavatus. Docking studies against 4URO (antibacterial target) and 5V5Z (antifungal target) gave docking scores of − 8.1 kcal/mol and − 9.1 kcal/mol, respectively, indicating strong binding interactions through hydrogen bonding, electrostatic, and hydrophobic forces. ADME profiling revealed high gastrointestinal absorption, blood–brain barrier permeability, selective P450 inhibition, and moderate bioavailability, highlighting ’s pharmacokinetic potential. Graphical abstracthttps://doi.org/10.1007/s44371-025-00195-yClaisen-Schmidt condensationSingle-crystal X-ray diffractionDFT/B3LYP calculationsAntimicrobial activityMolecular docking |
| spellingShingle | Nutan V. Sadgir Vishnu A. Adole Sunil L. Dhonnar Bapu S. Jagdale Kailas H. Kapadnis Jayesh Pawar Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies Discover Chemistry Claisen-Schmidt condensation Single-crystal X-ray diffraction DFT/B3LYP calculations Antimicrobial activity Molecular docking |
| title | Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies |
| title_full | Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies |
| title_fullStr | Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies |
| title_full_unstemmed | Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies |
| title_short | Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies |
| title_sort | synthesis structural elucidation and antimicrobial evaluation of 2e 3 4 fluorophenyl 1 4 isopropylphenyl prop 2 en 1 one insights from experimental and computational studies |
| topic | Claisen-Schmidt condensation Single-crystal X-ray diffraction DFT/B3LYP calculations Antimicrobial activity Molecular docking |
| url | https://doi.org/10.1007/s44371-025-00195-y |
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