New Method for the Synthesis of Ether Derivatives of Artemisinin

Bora, Pranjal P.; Baruah, Nabajyoti; Bez, Ghanashyam; Barua, Nabin C.

doi:10.1080/00397911.2010.538887

Cited by 10 publications

(8 citation statements)

References 9 publications

(6 reference statements)

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“…Compound 11 was prepared in 51 % yield by an etherification reaction between alcohol 21 and dihydroartemisinin using phosphotungstic acid as catalyst instead of BF 3 etherate. This procedure was already reported in the context of the synthesis of other dihydroartemisinin ether derivatives . Notably, ether 11 was isolated as a mixture of C10‐α‐ and C10‐β‐diastereomers (ratio C10‐α/C10‐β=1:2) and because it was not possible to separate these two isomers from each other, the mixture was applied for biological tests.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Artemisinin‐Derived Dimers, Trimers and Dendrimers: Investigation of Their Antimalarial and Antiviral Activities Including Putative Mechanisms of Action

Fröhlich

Hahn

Belmudes

et al. 2018

Chemistry A European J

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Generation of dimers, trimers and dendrimers of bioactive compounds is an approach that has recently been developed for the discovery of new potent drug candidates. Herein, we present the synthesis of new artemisinin-derived dimers and dendrimers and investigate their action against malaria parasite Plasmodium falciparum 3D7 strain and human cytomegalovirus (HCMV). Dimer 7 was the most active compound (EC 1.4 nm) in terms of antimalarial efficacy and was even more effective than the standard drugs dihydroartemisinin (EC 2.4 nm), artesunic acid (EC 8.9 nm) and chloroquine (EC 9.8 nm). Trimer 4 stood out as the most active agent against HCMV in vitro replication and exerted an EC value of 0.026 μm, representing an even higher activity than the two reference drugs ganciclovir (EC 2.60 μm) and artesunic acid (EC 5.41 μm). In addition, artemisinin-derived dimer 13 and trimer 15 were for the first time both immobilized on TOYOPEARL AF-Amino-650M beads and used for mass spectrometry-based target identification experiments using total lysates of HCMV-infected primary human fibroblasts. Two major groups of novel target candidates, namely cytoskeletal and mitochondrial proteins were obtained. Two putatively compound-binding viral proteins, namely major capsid protein (MCP) and envelope glycoprotein pUL132, which are both essential for HCMV replication, were identified.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Artemisinin‐Derived Dimers, Trimers and Dendrimers: Investigation of Their Antimalarial and Antiviral Activities Including Putative Mechanisms of Action

Fröhlich

Hahn

Belmudes

et al. 2018

Chemistry A European J

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“…The hybridization of natural products was reported to have antimalarial, anticancer, and antiviral activity. Within our scope of antiherpetic activities, artemisinin-egonol (38) and artemisinin-homoegonol hybrids (39) were obtained via etherification reactions [141,187]. They exhibited strong anti-HCMV activity with EC 50 values of 0.17 and 0.13 µM, respectively [188].…”

Section: Miscellaneous Compounds With Potential Antiherpetic Activitiesmentioning

confidence: 99%

Natural Products and Their Derivatives against Human Herpesvirus Infection

et al. 2021

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Herpesviruses establish long-term latent infection for the life of the host and are known to cause numerous diseases. The prevalence of viral infection is significantly increased and causes a worldwide challenge in terms of health issues due to drug resistance. Prolonged treatment with conventional antiviral drugs is more likely to develop drug-resistant strains due to mutations of thymidine nucleoside kinase or DNA polymerase. Hence, the development of alternative treatments is clearly required. Natural products and their derivatives have played a significant role in treating herpesvirus infection rather than nucleoside analogs in drug-resistant strains with minimal undesirable effects and different mechanisms of action. Numerous plants, animals, fungi, and bacteria-derived compounds have been proved to be efficient and safe for treating human herpesvirus infection. This review covers the natural antiherpetic agents with the chemical structural class of alkaloids, flavonoids, terpenoids, polyphenols, anthraquinones, anthracyclines, and miscellaneous compounds, and their antiviral mechanisms have been summarized. This review would be helpful to get a better grasp of anti-herpesvirus activity of natural products and their derivatives, and to evaluate the feasibility of natural compounds as an alternative therapy against herpesvirus infections in humans.

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“…[24] Aldehydes are used as substrates instead of alkynes, which are applied in CuAAC. Thus, for metal-free click reaction, we used ARN-derived aldehydes 31-33 and the previously applied azide 22 to form hybrids 8, 10,a nd 12.T he aldehydes were obtained by etherification of DHA with the corresponding alco- hols, [26] catalyzed by H 3 PW 12 O 4 •H 2 O( Scheme1D), and subsequent Dess-Martin oxidation reaction to obtain aldehydes. Because am ixture of both DHA isomersw as used, the alpha and beta isomers of the ARN-derived alcohols were formed.…”

Section: Chemistrymentioning

confidence: 99%

(Iso)Quinoline–Artemisinin Hybrids Prepared through Click Chemistry: Highly Potent Agents against Viruses

Çapcı

Lorion

Mai

et al. 2020

Chemistry A European J

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Viral infections cause life‐threatening diseases in millions of people worldwide every year and there is an urgent need for new, effective antiviral drugs. Hybridization of two chemically diverse compounds into a new bioactive effector product is a successful concept to improve the properties of a hybrid drug relative to the parent compounds. In this study, (iso)quinoline–artemisinin hybrids, obtained through copper‐catalyzed azide–alkyne cycloaddition or metal‐free click reactions (in organic solvents or in the presence of water), were analyzed in vitro, for the first time, for their inhibitory activity against human cytomegalovirus (HCMV), relative to their parent compounds and the reference drug ganciclovir. EC50 (HCMV) values were obtained in a range 0.22–1.20 μm, which indicated highly potent antiviral properties in the absence of cytotoxic effects on normal cells (CC50>100 μm). The most active hybrid, 1 (EC50=0.22 μm), is 25 times more potent than its parent compound artesunic acid (EC50=5.41 μm) and 12 times more efficient than the standard drug ganciclovir (EC50=2.6 μm). Interestingly, hybrid 1 also shows inhibitory activity against hepatitis B virus in vitro (EC50 (HBeAg)=2.57 μm).

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New Method for the Synthesis of Ether Derivatives of Artemisinin

Cited by 10 publications

References 9 publications

Synthesis of Artemisinin‐Derived Dimers, Trimers and Dendrimers: Investigation of Their Antimalarial and Antiviral Activities Including Putative Mechanisms of Action

Synthesis of Artemisinin‐Derived Dimers, Trimers and Dendrimers: Investigation of Their Antimalarial and Antiviral Activities Including Putative Mechanisms of Action

Natural Products and Their Derivatives against Human Herpesvirus Infection

(Iso)Quinoline–Artemisinin Hybrids Prepared through Click Chemistry: Highly Potent Agents against Viruses

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