6298-23-3

Upstream product

• 24035-44-7 13-isopropyl-12-methoxypodocarpa-8,11,13-trien-19-ol 
• 959681-33-5 C₂₇H₄₄O₃Si 
• 24035-61-8 methyl (+)-12-methoxyabieta-8,11,13-trien-19-oate 
• 29271-65-6 methyl 13-α-hydroxyisopropyl-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 29271-64-5 methyl 13-acetyl-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 24099-80-7 methyl 13-isopropenyl-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 1260143-29-0 12-(benzyloxy)abieta-8,11,13-trien-19-ol 
• 24402-25-3 7-Isopropyl-6-acetyl-desoxy-podocarpsaeure-methylester 
• 24035-60-7 methyl (1S,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate 
• 116032-84-9 18-Oxoferruginol 
• 62751-54-6 8β-Benzoyloxy-12-oxoabieta-9(11),13-dien-18-saeuremethylester 
• 13742-23-9 (1R,4aS,10aR)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 928819-28-7 C₂₃H₃₆O₅ 
• 928819-29-8 methyl 12α-chloroabietate 

Relevant academic research and scientific papers

Biological profiling of semisynthetic C19-functionalized ferruginol and sugiol analogues

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.

Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies

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 (+)-hanagokenol A, (+)-fortunins E, G, H, and (-)-sugikurojin A from abietic acid

A series of 12-hydroxy-substituted abietane diterpenes, functionalized on C19 or C18, have been synthesized starting from 18-hydroxyferruginol. The first synthesis of antibacterial hanagokenol A and fortunins E, G, and H, and a new procedure for preparing

First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid

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.

Synthesis of phenol abietane diterpenes based on the oxidative radical cyclization utilizing the Mn(OAc)3/Ac2O system

A new route to phenol abietane diterpenes from trans-communic acid is reported. The key step is the transformation of a β-ketoester into the corresponding O-acetylsalicilate, via a manganese(III)-based oxidative free-radical cyclization carried out in Ac2O. Utilizing this, the first synthesis of (-)-sugikurojin A has been achieved. The immunosuppressor 19-hydroxyferruginol has also been synthesized. Georg Thieme Verlag Stuttgart.

18-OXOFERRUGINOL FROM THE LEAF OF TORREYA NUCIFERA

From the leaf of the conifer Torreya nucifera, a new diterpenoid has been isolated and shown to be 18-oxoferruginol (12-hydroxy-8,11,13-abietatrien-18-al) on the basis of its spectroscopic properties and its chemical conversion to the known 18-hydroxyferruginol (8,11,13-abietatriene-12,18-diol). - Key Word Index: Torreya nucifera; Taxaceae; diterpenoids; abietanes; 18-oxoferruginol.

PHENOLIC DITERPENOIDS OF PODOCARPUS FERRUGINEUS AND OTHER PODOCARPS

19-Hydroxyferruginol and 19-acetoxyferruginol, two new naturally occuring phenolic diterpenoids, have been isolated from the heartwood of Podocarpus ferrugineus.Totarol and its derivatives have been obtained from Podocarpus affinis, P. falcatus, P. koordersii, Dacrycarpus vieillardii and Decussocarpus comptonii and podocarpic acid from Falcatifolium taxoides. - Keywords: Podocarpus ferrugineus; Podocarpus spp.; Dacrycarpus vieillardii; Decussocarpus comptonii; Prumnopitys ferrugineus; Falcatifolium taxoides; Podocarpaceae; phenolic diterpenoids; 19-hydroxyferruginol; 19-acetoxyferruginol; chemotaxonomy.