Total synthesis and biological evaluation of (-)-atrop-abyssomicin C
Само за регистроване кориснике
2013
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.
Извор:
Organic & Biomolecular Chemistry, 2013, 11, 33, 5413-5424Издавач:
- Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
- Развој нових синтетичких метода и њихова примена у синтези природних производа и биолошки активних једињења (RS-MESTD-Basic Research (BR or ON)-172027)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
DOI: 10.1039/c3ob40692j
ISSN: 1477-0520
PubMed: 23839049
WoS: 000323141800005
Scopus: 2-s2.0-84881172859
Институција/група
IHTMTY - JOUR AU - Bihelović, Filip AU - Karadžić, Ivanka AU - Matović, Radomir AU - Saičić, Radomir N. PY - 2013 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1214 AB - Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells. PB - Royal Soc Chemistry, Cambridge T2 - Organic & Biomolecular Chemistry T1 - Total synthesis and biological evaluation of (-)-atrop-abyssomicin C VL - 11 IS - 33 SP - 5413 EP - 5424 DO - 10.1039/c3ob40692j ER -
@article{ author = "Bihelović, Filip and Karadžić, Ivanka and Matović, Radomir and Saičić, Radomir N.", year = "2013", abstract = "Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Organic & Biomolecular Chemistry", title = "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C", volume = "11", number = "33", pages = "5413-5424", doi = "10.1039/c3ob40692j" }
Bihelović, F., Karadžić, I., Matović, R.,& Saičić, R. N.. (2013). Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry Royal Soc Chemistry, Cambridge., 11(33), 5413-5424. https://doi.org/10.1039/c3ob40692j
Bihelović F, Karadžić I, Matović R, Saičić RN. Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry. 2013;11(33):5413-5424. doi:10.1039/c3ob40692j .
Bihelović, Filip, Karadžić, Ivanka, Matović, Radomir, Saičić, Radomir N., "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C" in Organic & Biomolecular Chemistry, 11, no. 33 (2013):5413-5424, https://doi.org/10.1039/c3ob40692j . .