116032-84-9Relevant academic research and scientific papers
GENERAL ENTRY TO THE SYNTHESIS OF OPTICALLY ACTIVE DITERPENOIDS OF C-20β SERIES
Node, Manabu,Hao, Xiao-jiang,Nagasawa, Hideko,Fuji, Kaoru
, p. 4141 - 4144 (1989)
(+)-Podocarpic acid (2) and (+)-lambertic acid (3) were synthesized from (S)-(-)-nitroolefin 1a.
Biological profiling of semisynthetic C19-functionalized ferruginol and sugiol analogues
González-Cardenete, Miguel A.,Rivas, Fatima,Basset, Rachel,Stadler, Marco,Hering, Steffen,Padrón, José M.,Zaragozá, Ramón J.,Dea-Ayuela, M. Auxiliadora
, p. 1 - 11 (2021)
The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure-activity relationship (SAR) elements. In particular, the ferruginol and sugiol analogs compounds 10-16 were characterized by the presence of a phenol moiety, higher oxidization states at C-7 (ketone), and the hydroxyl, methyl ester or free carboxylic acid at C19. The biological profiling of these compounds was investigated against a panel of six human solid tumor cell lines (HBL-100, A549, HeLa, T-47D, SW1573 and WiDr), four parasitic Leishmania species (L. donovani, L. infantum, L. guyanensis and L. amazonensis) and two malaria strains (3D7 and K1). Furthermore, the capacity of the compounds to modulate gamma-aminobutyric acid type A (GABAA) receptors (α1β2γ2s) is also described. A comparison of the biological results with those previously reported of the corresponding C18-functionalized analogs was conducted.
A Suzuki–Miyaura Coupling of ortho-Hydroxyaryl Bromide with Isopropenylboronic Pinacol Ester: Synthesis of the Potassium-Channel Opener (+)-Callitrisic Acid
Wu, Xiongyu,Silver? Ejneby, Malin,Ottosson, Nina E,Elinder, Fredrik,Konradsson, Peter
, p. 1730 - 1734 (2018)
A Suzuki–Miyaura coupling reaction of ortho-hydroxyaromatic bromide 8 with isopropenylboronic acid pinacol ester has been investigated. It was found that the catalyst of Pd2(dba)3/PCy3 in dioxan-water gave good yield by suppressing the formation of isomeric side product 14. (+)-Callitrisic acid was synthesized from (+)-podocarpic acid using this condition with an overall yield of 54 % in about five steps. (+)-Callitrisic acid was found to be almost three times more potent than dehydroabietic acid to open a voltage-gated potassium channel.
Total Synthesis of (+)-Podocarpic and (+)-Lambertic Acids
Hao, Xiao-jiang,Node, Manabu,Fuji, Kaoru
, p. 1505 - 1510 (2007/10/02)
A concise synthesis, from the chiral nitroalkene 1a, of (+)-podocarpic acid is described.This was transformed into (+)-lambertic acid via a chromium complex.
