A diverse array of biologically active derivatives was derived by modifying the chemically active sites of dehydroabietylamine. Herein, we describe the synthesis of a new series of C-19-arylated dehydroabietylamine derivatives using a palladium-catalyzed C(sp)-H activation reaction. Five analogues (, , , , and ) exhibited antibacterial activity against . Compound exhibited strong inhibitory activity against DNA Topo II and Topo IV. Molecular docking modeling indicated that it can bind effectively to the target through interactions with amino acid residues. The synthesized compounds were tested for their antifungal activity against six common phytopathogenic fungi. The mechanism of action of compound against was investigated, revealing that it disrupts the morphology of the mycelium and enhances cell membrane permeability.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.jnatprod.3c01213 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Novel Dehydroabietylamine C-Ring Schiff Base Derivatives: Synthesis, Antiproliferative activity, DNA binding and Molecular docking.
Chem Asian J
January 2025
College of Science, Nanjing Forestry University, Nanjing, Jiangsu, 210037, China.
A series of Dehydroabietylamine (DHAA) C-ring Schiff derivatives, L-L, were synthesized and their in vitro cytotoxic activity against the human tumor cell lines cervix HeLa, breast MCF-7, lung A549, liver HepG2, and the nonmalignant cell line umbilical vein HUVEC was investigated. Most of the compounds showed varying degrees of anticancer activity against HeLa cell lines while demonstrating lower toxicity to normal HUVEC cells compared to DHAA and doxorubicin (DOX), especially compound L, which not only enhanced the anticancer activity of DHAA, but also significantly reduced the toxicity to normal cells, achieving a selectivity index (SI) 118 times higher than that of DHAA and 245 times higher than that of DOX. In addition, Compound L induced apoptosis in HeLa cells in a dose-dependent manner, suppressed the expression of the anti-apoptotic protein Bcl-2, and arrested the cell cycle at the S phase.
View Article and Find Full Text PDFDesign, synthesis, and evaluation of dehydroabietyl imidazolidine-2,4-diones, 2,4,5-triones, and 2-thioxoimidazolidine-4,5-diones as TDP1 inhibitors and dual TDP1/TDP2 inhibitors.
Arch Pharm (Weinheim)
January 2025
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch Russian Academy of Sciences, Novosibirsk, Russian Federation.
Tyrosyl DNA phosphodiesterases 1 and 2 (TDP1 and TDP2), which are enzymes involved in the repair of DNA, are regarded as promising targets for the development of new anticancer drugs. In this study, a series of imidazolidine-2,4-diones, 2,4,5-triones, and 2-thioxoimidazolidine-4,5-diones based on dehydroabietylamine (DHAAm) were synthesized. The inhibitory activity of the new compounds against TDP1 and TDP2, as well as their cytotoxic characteristics, were evaluated.
View Article and Find Full Text PDFDehydroabietylamine-substituted trifluorobenzene sulfonamide rhodamine B hybrids as anticancer agents overcoming drug resistance.
Eur J Med Chem
October 2024
University Clinic for Internal Medicine IV, Hematology/Oncology, Medical Faculty, Martin-Luther-University Halle-Wittenberg, Ernst-Grube-Str. 40, D-06120, Halle (Saale), Germany.
Article Synopsis
- * These conjugates demonstrated low inhibitory concentration (IC) values between 0.2 and 0.7 μM across various tumor cell lines, indicating their effectiveness as potential cancer treatments.
- * The DHA-derived conjugate showed superior selectivity for tumor cells over non-malignant cells and was also effective against drug-resistant tumors, functioning independently of carbonic anhydrase IX expression.
Discovery of Dehydroabietylamine Derivatives as Antibacterial and Antifungal Agents.
J Nat Prod
April 2024
Jiangsu Key Laboratory of Pesticide, College of Sciences, Nanjing Agricultural University, Nanjing 210095, People's Republic of China.
A diverse array of biologically active derivatives was derived by modifying the chemically active sites of dehydroabietylamine. Herein, we describe the synthesis of a new series of C-19-arylated dehydroabietylamine derivatives using a palladium-catalyzed C(sp)-H activation reaction. Five analogues (, , , , and ) exhibited antibacterial activity against .
View Article and Find Full Text PDFDehydroabietane-type bifunctional organocatalysts in asymmetric synthesis: recent progress.
RSC Adv
October 2023
College of Pharmacy, Guangxi University of Chinese Medicine, Guangxi Zhuang Yao Medicine Center of Engineering and Technology Nanning 530200 China
Dehydroabietane-type bifunctional organocatalysts derived from rosane-type diterpenes of dehydroabietic acid (DHAA) and dehydroabietylamine (DA) have been utilized in a wide variety of highly enantioselective reactions. Since one well-documented review exclusively reported on the development of terpene-derived bifunctional thioureas in asymmetric organocatalysis in 2013, fragmentary progress on the dehydroabietane-type bifunctional thioureas and squaramides has been mentioned in other reviews. In this mini-review, we systematically analyze and reorganize the published literature on dehydroabietane-type bifunctional organocatalysts in the recent decade according to the type of catalysts.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!