14022-44-7Relevant articles and documents
Synthesis and biological evaluation of (-)-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool
Novoa, María L.,Escalante, Yelisbeth,Maldonado, Liliana,Galindo-Castro, Iván,álvarez, Annamil,Figarella, Katherine,Marsiccobetre, Sabrina,Arocha, Irina,Nieves, Jais,Salazar, Franklin,Gámez, Carlos,Canudas, Nieves,Tropper, Eleonora,González, Teresa,Villamizar, José E.
supporting information, p. 207 - 212 (2015/11/09)
13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6-C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.
The synthesis and antibacterial activity of totarol derivatives. Part 1: Modifications of ring-C and pro-drugs
Evans, Gary B.,Furneaux, Richard H.,Gravestock, Michael B.,Lynch, Gregory P.,Scott, G.Kenneth
, p. 1953 - 1964 (2007/10/03)
A series of analogues of, and potential pro-drugs derived from, the potent antibacterial diterpene totarol (1) were synthesized in order to elucidate the minimum structural requirements for antibacterial activity and to seek compounds with good bioavailability in vivo. These analogues varied in the structural features of their aromatic rings and the prodrugs were O-glycosylated derivatives. They were tested in vitro against three Gram-positive bacteria: β-lactamase-positive and high level gentamycin-resistant Enterococcus faecalis, penicillin-resistant Streptococcus pneumoniae, and methicillin-resistant Staphylococcus aureus (MRSA); and against the Gram-negative multi-drug-resistant Klebsiella pneumoniae. None of the analogues was more potent than totarol itself, which is effective against these Gram-positive bacteria at MIC values of 7 μM. The results were evaluated in terms of a structure-activity relationship and this showed that a phenolic moiety was essential for potent antibacterial activity. Amongst the pro-drugs, totaryl α-D-mannopyranoside (22) proved the most active in vitro (MIC 18 μM). The in vivo antibacterial activities of compounds 1, 22 and totarol β-lactoside (23) were assessed in a mouse model of infection, but they were found to be ineffective. Compounds 1 and 22 were shown to be cytotoxic towards proliferating human cell cultures, CH 2983, HeLa, and MG 63, but only at concentrations of > 30 μM.