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Merck
CN
  • Diosgenone synthesis, anti-malarial activity and QSAR of analogues of this natural product.

Diosgenone synthesis, anti-malarial activity and QSAR of analogues of this natural product.

Molecules (Basel, Switzerland) (2013-03-16)
Adriana Pabón, Gustavo Escobar, Esteban Vargas, Víctor Cruz, Rafael Notario, Silvia Blair, Fernando Echeverri
摘要

Solanum nudum Dunal steroids have been reported as being antimalarial compounds; however, their concentration in plants is low, meaning that the species could be threatened by over-harvesting for this purpose. Swern oxidation was used for hemisynthesis of diosgenone (one of the most active steroidal sapogenin diosgenin compounds). Eighteen structural analogues were prepared; three of them were found to be more active than diosgenone (IC50 27.9 μM vs. 10.1 μM, 2.9 μM and 11.3 μM). The presence of a 4-en-3-one grouping in the A-ring of the compounds seems to be indispensable for antiplasmodial activity; progesterone (having the same functional group in the steroid A-ring) has also displayed antiplasmodial activity. Quantitative correlations between molecular structure and bioactivity were thus explored in diosgenone and several derivatives using well-established 3D-QSAR techniques. The models showed that combining electrostatic (70%) and steric (30%) fields can explain most variance regarding compound activity. Malarial parasitemia in mice became reduced by oral administration of two diosgenone derivatives.

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Supelco
17α-羟孕酮标准液 溶液, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®