Artemisinin and its derivatives: a novel class of anti-malarial and anti-cancer agents

Abstract

In this tutorial review, an effort towards presentation of a comprehensive account of the recent developments on various kinds of artemisinin derivatives including artemisinin dimers, trimers and tetramers has been made and their efficacy towards malaria parasites and different cancer cells lines was compared with that of artemisinins, and various other anti-malarial and anti-cancer drugs. It is expected that this review will provide first-hand information on artemisinin chemistry to organic/medicinal chemists, and pharmacologists working on anticancer and anti-malarial drug development.

Synthesis and Cytotoxicity of Novel 10-Substituted Dihydroartemisinin Derivatives Containing N-Arylphenyl-ethenesulfonamide Groups

“…The high chemical sensitivity of the artemisinin molecule restricts broad derivatization for library synthesis for further clinical development. So far the majority of the artemisinin derivatizations were carried out on the C-10 acetal and to a lesser extent on the C-13 carbon [8]. The observation that dihydroartemisinin C-10 ester, ether or amide derivatives ( Figure 1) possess significant antitumor activity prompted previous efforts, both within our group [9,10] and by others [11][12][13].…”

“…The white crystals were filtered, washed with ethyl acetate, and dried to yield white solid 7 (23 g, 99%). m. (8) A mixture of compound 7 (10 g, 0.053 mol) and POCl 3 (100 mL, 1.1 mol) was stirred at 80 °C for 2 h and then cooled to room temperature. The solvent was removed under vacuum, 100 mL of toluene was added, and stirred for 10 min.…”

Comparison of Density Functional in the Study of Electronic Properties of Artemisinin Derivatives

“…[23][24][25][26][27][28] Desta forma, este trabalho teve como objetivo principal comparar o desempenho dos diversos funcionais de densidade do formalismo DFT, disponíveis no software The General Atomic and Molecular Electronic Structure System (GAMESS), 29 que faz uso de código aberto (software livre), utilizando a artemisinina e alguns de seus derivados (Figura 3) como estudo de caso, na obtenção de propriedades eletrônicas destes compostos. De forma geral, a estrutura dos compostos abordados nesse estudo é de porte médio, sendo, assim, o DFT uma boa escolha para a solução aproximada da equação eletrônica de Schrödinger, já que computacionalmente é menos dispendioso quando comparado a outros como Coupled Cluster 30 e Interação de Configurações e, também, mais eficiente quando comparado ao HF, já que leva em consideração a correlação eletrônica.…”

Singlet oxygen addition to cyclo-1,3-hexadienes from natural sources and from organocatalytic enal dimerization

“…7 The enormous potency of the natural product that involves also anti-cancer drug activity just recently emerged. 8,9 At the same time, however, reports appeared that describe the appearance of plasmodium species resistant against artemisinin and artemisinin-derivatives. 10,11 Three approaches are currently under investigation to deal with this fatal trend: a) artemisinin combination therapy (ACT, with other non-peroxidic antimalarial drugs), 12 b) new peroxidic substances following the structural prototype, 13,14 c) dyade concepts 15 involving structure combinations of two artemisinin monomers, 16 artemisinin and quinolines, 17 or artemisinin derivatives with synthetic 1,2,4-trioxane structures.…”