Recent advances in the total synthesis of pharmaceutically relevant diterpenes

Busch, Torsten; Kirschning, Andreas

doi:10.1039/b705652b

Cited by 42 publications

(15 citation statements)

References 68 publications

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“…15 The diterpenes 8-10 belong to a growing family of nontaxane-based microtubule stabilizers that have received great attention for synthetic and SAR studies during the past decade. 16 Many successful protocols rely on using natural (+)-carvone 10b-d or (-)-cryptone 12b as the starting material. Our easy assess to both enantiomers of 6b will open a new avenue to access these biologically important molecules.…”

mentioning

confidence: 99%

Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

Wang

2008

Org. Lett.

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mentioning

confidence: 99%

Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

Wang

2008

Org. Lett.

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“…The challenges of the synthetic chemist in the synthesis of pharmaceutical relevant diterpenes has been emphasized in a recent review article [5] and corroborates with the concept that a validated QSAR predictive model can be of valuable aid in the choice of which compounds of a data source may receive priority attention for biological tests. To our knowledge, this is the first QSAR study that makes available a compound set with predicted IC 50 values of clerodane diterpenoids.…”

Section: Introductionmentioning

confidence: 79%

“…The TAE descriptor Fuk5 relates to the Fukui F þ function scalar value [25,26] F þ (r) ¼ r HOMO (r) (5) where r HOMO is the electron density of the highest occupied molecular orbital (HOMO) at a point r in the space around the molecule. It characterizes nucleophilic attack and describes radical reactivity entailed to a surface area and the 5 th bin is an average value of this function.…”

Section: Internal and External Validationmentioning

confidence: 99%

QSAR of Clerodane Diterpenoids with Cytotoxic and Antitumoral Activity Against V‐79 Cells

Cramer

Takahata

2009

QSAR Comb. Sci.

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This work deals with diterpenoids of the clerodane type, compounds isolated from the extracts of different plant organs from trees mainly of the Flacourtiaceae family. The aim of the present work is to study Quantitative Structure-Activity Relationship (QSAR) on Casearins isolated from the crude plant extract of the leaves of the shrub tree Casearia sylvestris Swartz, Flacourtiaceae, that show cytotoxic activities against V-79 Chinese Hamster lung cells. In total, ca. 2080 descriptors and indices were calculated for the QSAR study using various softwares. The obtained QSARs with three descriptors were developed using two independent methods, Multiple Linear Regression (MLR) and Support Vector Machine (SVM), using a small set of molecules. For external validation of the MLR QSAR we employed a training/test set that was evaluated through criteria ruled by RQK fitness functions. Both MLR and SVM QSARs were validated using the same test set, where the SVM QSAR achieved the best results. Both QSARs were applied to a data set with 113 clerodane diterpenoids never tested before against the Chinese Hamster lung fibroblast V-79 cells, and also applied to thirteen new compounds which were build in silico, adding fluorine and chlorine atoms as substituents at specific positions of the clerodane diterpenoids. Encouraging results were obtained in both cases which serve as an indicator for further studies in silico and/or bioassay of these compounds as anticancer agents.

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“…For example, the paclitaxel content is only at 10-ppm level in the most productive species, Taxus brevifolia 38 . In addition, complex diterpenoids molecules are quite difficult for chemical synthesis de novo 39 . Therefore, heterologous expression of the pathways in microbes is very promising for diterpenoids production.…”

Section: Heterologous Biosynthesis Of Major Classes Of High Value mentioning

confidence: 99%

Engineered biosynthesis of natural products in heterologous hosts

et al. 2015

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Natural products produced by microorganisms and plants are a major resource of antibacterial and anticancer drugs as well as industrially useful compounds. However, the native producers often suffer from low productivity and titers. Here we summarize the recent applications of heterologous biosynthesis for the production of several important classes of natural products such as terpenoids, flavonoids, alkaloids, and polyketides. In addition, we will discuss the new tools and strategies at multi-scale levels including gene, pathway, genome and community levels for highly efficient heterologous biosynthesis of natural products.

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Recent advances in the total synthesis of pharmaceutically relevant diterpenes

Cited by 42 publications

References 68 publications

Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

QSAR of Clerodane Diterpenoids with Cytotoxic and Antitumoral Activity Against V‐79 Cells

Engineered biosynthesis of natural products in heterologous hosts

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