Design, Synthesis, and Biological Evaluation of Some Novel o-aminophenol Derivatives.
| Title: | Design, Synthesis, and Biological Evaluation of Some Novel o-aminophenol Derivatives. |
|---|---|
| Authors: | Nguyen DV; Department of Chemistry, Hanoi National University of Education, Hanoi, Vietnam.; Tran LD; Department of Chemistry, Hanoi National University of Education, Hanoi, Vietnam.; Vu PUN; Department of Chemistry, Hanoi National University of Education, Hanoi, Vietnam.; Meervelt LV; Department of Chemistry, KU Leuven, Celestijnenlaan, 200F, B-3001 Leuven, Belgium.; Nguyen MNT; Department of Science, Hong Duc University, Thanh Hoa, Vietnam.; Ngo AL; Department of Chemistry, Hanoi National University of Education, Hanoi, Vietnam.; Duong HQ; Department of Chemistry, Hanoi National University of Education, Hanoi, Vietnam. |
| Source: | Current organic synthesis [Curr Org Synth] 2025; Vol. 22 (6), pp. 754-768. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Bentham Science Publishers Country of Publication: United Arab Emirates NLM ID: 101208457 Publication Model: Print Cited Medium: Internet ISSN: 1875-6271 (Electronic) Linking ISSN: 15701794 NLM ISO Abbreviation: Curr Org Synth Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Saif Zone, Sharjah, U.A.E. ; San Francisco, CA : Bentham Science Publishers, c2004- |
| MeSH Terms: | Aminophenols*/pharmacology ; Aminophenols*/chemical synthesis ; Aminophenols*/chemistry ; Antioxidants*/pharmacology ; Antioxidants*/chemical synthesis ; Antioxidants*/chemistry ; Antineoplastic Agents*/chemical synthesis ; Antineoplastic Agents*/pharmacology ; Antineoplastic Agents*/chemistry ; Anti-Bacterial Agents*/pharmacology ; Anti-Bacterial Agents*/chemical synthesis ; Anti-Bacterial Agents*/chemistry ; Anti-Infective Agents*/chemical synthesis ; Anti-Infective Agents*/pharmacology ; Anti-Infective Agents*/chemistry ; Drug Design*; Fungi/drug effects ; Biphenyl Compounds/antagonists & inhibitors ; Humans ; Microbial Sensitivity Tests ; Cell Line, Tumor ; Structure-Activity Relationship ; Molecular Structure ; Drug Screening Assays, Antitumor |
| Abstract: | Background: o-Aminophenol derivatives are of particular interest for their diverse biological activities and potential therapeutic applications. Such as, antioxidant, antibacterial, and cytotoxic activities.; Objectives: This study aimed to design and synthesize a series of novel o-aminophenol derivatives through an efficient multi-step process, characterize them using modern spectroscopic techniques, and evaluate their antimicrobial, antioxidant, and cytotoxic activities.; Methods: A series of novel derivatives of o-aminophenol have been successfully synthesized with very high efficiency through a simple six-step process using readily available chemicals and straightforward reactions. The structures of all products were accurately determined using modern spectroscopic methods such as 1D and 2D NMR, as well as IR, MS spectroscopy, and X-ray methods. The antimicrobial activities of eight o-nitrophenol derivatives were assessed against Gram (-) and Gram (+) bacteria as well as fungi. In comparison, antioxidant activities were tested for two o-nitrophenol and 11 o-aminophenol derivatives using SC50 and EC50 assays. Cytotoxicity was evaluated on KB, HepG2, A549, and MCF7 cancer cell lines.; Results: Six synthesized compounds 5b, 5c, 5g, 6b, 6c, 6g exhibited unusual doublet signals in the H8 region of the 1H NMR spectrum, attributed to atropisomer formation. Eight o-nitrophenol derivatives demonstrated weak antimicrobial activity, with MIC values ranging from 100 to 200 μg/mL. Compound 5g showed activity against all tested bacterial and fungal strains. In antioxidant testing, eight o-aminophenol derivatives 6a, 6b, 6c, 6e, 6f, 6h, 6i, and 12b displayed excellent activity, with SC50 values between 18.95 and 34.26 μg/mL, approaching ascorbic acid's SC50 value of 12.60 μg/mL. Three derivatives 6d, 6g, and 12a showed superior antioxidant activity with EC50 values between 4.00 and 11.25 μg/mL, surpassing quercetin's standard of 9.8 μg/mL. Cytotoxicity assays revealed that oaminophenol derivatives 6b, 6c, 6f, 6i, and 12b exhibited moderate inhibitory effects on KB cell lines with IC50 values from 32 to 74.94 μg/mL. Compound 6i demonstrated moderate cytotoxic activity against HepG2, A549, and MCF7 cell lines, with IC50 values of 29.46, 71.29, and 80.02 μg/mL, respectively.; Conclusion: Design, synthesis, antimicrobial activity, DPPH Radical Scavenging, Cytotoxic activity, Evaluation of H8 signal anomalies in certain compounds, and Single crystal X-ray diffraction analysis.; (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.) |
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| Contributed Indexing: | Keywords: N-acetyl; antibacterial activity; antioxidant activity; atropisomer; cytotoxic activity.; o-aminophenol; o-nitrophenol; vanillin |
| Substance Nomenclature: | 0 (Aminophenols); 0 (Antioxidants); 0 (Antineoplastic Agents); 0 (Anti-Bacterial Agents); 23RH73DZ65 (2-aminophenol); 0 (Anti-Infective Agents); 0 (Biphenyl Compounds) |
| Entry Date(s): | Date Created: 20250214 Date Completed: 20251020 Latest Revision: 20251020 |
| Update Code: | 20260130 |
| DOI: | 10.2174/0115701794360303250109065121 |
| PMID: | 39950292 |
| Database: | MEDLINE |
Journal Article