823785-67-7Relevant articles and documents
Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against drosophila melanogaster til-til
Montenegro, Ivan,Pino, Luis,Werner, Enrique,Madrid, Alejandro,Espinoza, Luis,Moreno, Luis,Villena, Joan,Cuellar, Mauricio
, p. 4192 - 4208 (2013/06/26)
Natural compounds from Drimys winteri Forst and derivatives exhibited larvicidal effects against Drosophila melanogaster til-til. The most active compound was isodrimenin (4). The highest lethal concentration to the larvae of D. melanogaster was 4.5 ± 0.8 mg/L. At very low concentrations drimenol (1), confertifolin (3), and drimanol (5) displayed antifeedant and larvae growth regulatory activity. The antifeedant results of nordrimanic and drimanic compounds were better in first instar larvae. The EC50 value of polygodial (2) was 60.0 ± 4.2 mg/L; of diol 15 45.0 ± 2.8 mg/L, and of diol 17 36.9 ± 3.7 mg/L, while the new nordrimane compound 12 presented a value of 83.2 ± 3.5 mg/L.
Structural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues, supported by conformational and electronic studies
Derita, Marcos,Montenegro, Ivan,Garibotto, Francisco,Enriz, Ricardo D.,Fritis, Mauricio Cuellar,Zacchino, Susana A.
, p. 2029 - 2051 (2013/04/10)
Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5-17 obtained from 1-3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus
Hatzellis, Konstantinos,Pagona, Georgia,Spyros, Apostolos,Demetzos, Costas,Katerinopoulos, Haralambos E.
, p. 1996 - 2001 (2008/04/18)
In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5- methylene-1,2,3,4,4α,5,8,8α-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic irons isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a- dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).
A new route to 2,7- and 7-functionalized labdanes
Hersel, Ulrich,Steck, Melanie,Seifert, Karlheinz
, p. 1609 - 1615 (2007/10/03)
A new route for the synthesis of 2,7- and 7-functionalized labdanes starts from (R)-carvone (1). 11-Nordrim-7-en-9-one (15) is an appropriate starting material for the total synthesis of hispanone (21), a biologically active furolabdane isolated from the
Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone
Cheung, Wing Shun,Wong, Henry N. C.
, p. 11001 - 11016 (2007/10/03)
On the basis of the recently reported construction of (±)-hispanolone (2), the enantiomerically pure form of (-),2, employed in our partial synthesis of the specific platelet activating factor receptor antagonist prehispanolone (3), was prepared from (S)-
Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons
Wong, Henry N. C.
, p. 1757 - 1765 (2007/10/03)
The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7-dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2- trimethylsilylfurans to but-2-en-4-olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.
