Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular Structures and Conversion to Pharmacologically Important Skeletons
| Autor: | Rani R. Nair, Zabeera Kallingathodi, Ibrahim Ibnusaud, Simimole Haleema, Chithra Mohan, Sarath Muraleedharan Pillai, Rinshad V. Abdul, Chithra Gopinath, Deenamma Habel, Grace Thomas, Matthew Fritz, Andrew R. Puente, Jordan L. Johnson, Divya S. Nair, Prasad L. Polavarapu |
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| Rok vydání: | 2020 |
| Předmět: |
Pharmacology
Indole test Biological Products Pyrrolidines Natural product Molecular Structure Bicyclic molecule 010405 organic chemistry Stereochemistry Alkaloid Organic Chemistry Pharmaceutical Science Stereoisomerism Ring (chemistry) 01 natural sciences Pyrrolidine 0104 chemical sciences Analytical Chemistry 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Complementary and alternative medicine chemistry Drug Discovery Molecular Medicine Isoquinoline |
| Zdroj: | Journal of Natural Products. 83:2178-2190 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.0c00211 |
| Popis: | The versatility of the natural products (2S,3S)- and (2S,3R)-3-hydroxy-5-oxotetrahydrofuran-2,3-dicarboxylic acids (1 and 2), isolated in large amounts from tropical plant sources, has been demonstrated by the construction of 3-substituted and 3,4-disubstituted chiral pyrrolidine-2,5-diones. The absolute configurations of chiral pyrrolidine-2,5-diones have been ascertained using chiroptical spectroscopic methods and/or single-crystal XRD data. A combination of different reaction strategies delivering a diverse matrix of fused heterocyclic ring systems is presented. The pyrrolo[2,1-a]isoquinoline alkaloid (+)-crispine A possesses a wide range of pharmacological activities including antidepressant, antiplatelet, antileukemic, and anticancer activities. The analogues of indolizino[8,7-b]indole alkaloids (+)- and (-)-harmicine show strong antileishmanial, antinociceptive, PDE5-inhibitory, antimalarial, and antiviral activities. The bicyclic furo[2,3-b]pyrrolo skeleton is present in many natural products. Thus, the uniqueness of relatively cheap, naturally occurring chiral 2-hydroxycitric acid lactones as chirons has been demonstrated by the construction of some important molecular skeletons that are otherwise difficult to synthesize. |
| Databáze: | OpenAIRE |
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