13742-23-9Relevant academic research and scientific papers
First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid
Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Cabrera, Eduardo,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Lachkar, Mohammed,Messouri, Ibtissam
, p. 989 - 992 (2007)
A new route to 12-hydroxyabietic acid (10) and related compounds from abietic acid (12), via acetoxyalcohol 15, is reported. Utilizing this, the first synthesis of picealactone C (5) was achieved. The synthesis of natural 12-hydroxydehydroabietic acid (8), 18-hydroxyferruginol (9) and methyl 12α-hydroxyabietate (11) is also reported.
Late-stage C-H amination of abietane diterpenoids
Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
, 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.
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.
, 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.
Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives
Miyajima, Yui,Saito, Yohei,Takeya, Munehisa,Goto, Masuo,Nakagawa-Goto, Kyoko
, (2019/03/19)
The first syntheses of 4-epi-parviflorons A, C, and E (4-epi-1-3) were achieved in 12-13 steps from commercially available (-)-abietic acid (5). All synthesized compounds, including intermediates and derivatives, were evaluated for antiproliferative activity against five human tumor cell lines. A structure-activity relationship study revealed no significant difference between Pf E and 4-epi-Pf E, the importance of two oxygen functional groups at C-11 and C-12 for antiproliferative activity, as well as a combination of carbomethoxy at C-4 and a benzoyl ester with electron-drawing group at C-12 or hydroxymethyl at C-4 and an appropriate oxidation state of ring-B/C for triple-negative breast cancer cell selectivity.
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans -ozic acid
Li, Fu-Zhuo,Li, Shuang,Zhang, Peng-Peng,Huang, Zhi-Hui,Zhang, Wei-Bin,Gong, Jianxian,Yang, Zhen
, p. 12426 - 12429 (2016/10/24)
Ozonolysis of aromatic abietane (+)-carnosic acid (4) is used to create an important intermediate in an enantiomerically pure form, resulting in a simple, concise, readily scalable, and asymmetric synthesis of (-)-antrocin (1). This strategy not only provides an efficient approach to (-)-antrocin (1) synthesis but can also be readily adopted for the syntheses of optically pure (+)-asperolide C (2) and (-)-trans-ozic acid (3) from the naturally abundant aromatic abietanes (+)-podocarpic acid (5) and (+)-dehydroabietic acid (6). The strategy presented here is an example of the use of naturally occurring aromatic abietanes as a chiral pool and offers an account of the asymmetric synthesis of terpenoids.
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
