28625-40-3Relevant academic research and scientific papers
Friedel-Crafts reactions in ionic liquids: The counter-ion effect on the dealkylation and acylation of methyl dehydroabietate
Baleiz?o, Carlos,Pires, Natércia,Gigante, Bárbara,Marcelo Curto, Maria Jo?o
, p. 4375 - 4377 (2004)
Ionic liquids with different counter-ion and alkyl substitutes were tested as solvents in the dealkylation and acylation of methyl dehydroabietate, a useful and inexpensive building block for the synthesis of higher diterpenes derivatives. Ionic liquids with halogen counter-ions are very active in both reactions with high rate constant and conversion, avoiding the use of the conventional solvents (benzene and carbon disulfide) in these reactions. In the dealkylation reaction, the change of counter-ion from halogens to tetrafluoroborate had a dramatic effect on the stereoselectivity, showing the importance of the counter-ion in the course of the reactions.
The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: Modifications at C-12
Liu, Ming-Liang,Pan, Xue-Ying,Yang, Teng,Zhang, Wen-Ming,Wang, Tian-Qi,Wang, He-Yun,Lin, Hai-Xia,Yang, Cai-Guang,Cui, Yong-Mei
, p. 5492 - 5496 (2016)
A series of 12-oxime and O-oxime ether derivatives of dehydroabietic acid were synthesized and investigated for the antibacterial activity against Staphylococcus aureus Newman strain and five multidrug-resistant strains (NRS-1, NRS-70, NRS-100, NRS-108, a
Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies
Hamuli?, Damir,Stadler, Marco,Hering, Steffen,Padrón, José M.,Bassett, Rachel,Rivas, Fatima,Loza-Mejía, Marco A.,Dea-Ayuela, M. Auxiliadora,González-Cardenete, Miguel A.
supporting information, p. 823 - 831 (2019/03/19)
The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.
Late-stage C-H amination of abietane diterpenoids
Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
supporting information, p. 4736 - 4746 (2019/05/24)
This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.
Discovery of 12-Thiazole Abietanes as Selective Inhibitors of the Human Metabolic Serine Hydrolase hABHD16A
Ahonen, Tiina J.,Savinainen, Juha R.,Yli-Kauhaluoma, Jari,Kalso, Eija,Laitinen, Jarmo T.,Moreira, Vania M.
, p. 1269 - 1273 (2018/12/11)
Screening of an in-house library of compounds identified 12-thiazole abietanes as a new class of reversible inhibitors of the human metabolic serine hydrolase. Further optimization of the first hit compound lead to the 2-methylthiazole derivative 18, with an IC50 value of 3.4 ± 0.2 μM and promising selectivity. ABHD16A has been highlighted as a new target for inflammation-mediated pain, although selective inhibitors of hABHD16A (human ABHD16A) have not yet been reported. Our study presents abietane-type diterpenoids as an attractive starting point for the design of selective ABHD16A inhibitors, which will contribute toward understanding the significance of hABHD16A inhibition in vivo.
Use of 12-dehydroabietic acid oxime ether derivative
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Paragraph 0112; 0114, (2016/12/22)
The invention relates to a use of a 12-dehydroabietic acid oxime ether derivative. The 12-dehydroabietic acid oxime ether derivative has good inhibition activity on Staphylococcus aureus newman strains, and also has certain inhibition activity on some drug-resistant strains, such as NRS-1 strains ( aminoglycoside antibiotic and tetracycline resistant Staphylococcus aureus), NRS-70 strains (erythromycin and spectinomycin resistant Staphylococcus aureus), NRS-100 strains (oxacillin and tetracycline resistant Staphylococcus aureus), NRS-108 strains (gentamycin resistant Staphylococcus aureus) and NRS-271 strains (methicillin and linezolid resistant Staphylococcus aureus).
Novel BK channel openers containing dehydroabietic acid skeleton: Structure-activity relationship for peripheral substituents on ring C
Cui, Yong-Mei,Yasutomi, Eriko,Otani, Yuko,Yoshinaga, Takashi,Ido, Katsutoshi,Sawada, Kohei,Ohwada, Tomohiko
scheme or table, p. 5201 - 5205 (2009/05/07)
A series of dehydroabietic acid (DHAA, 2) derivatives was synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKα channels. Systematic modifications of the peripheral functionality of ring C of DHAA showed that t
