Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• borohydride to give the alcohol 25.9. 2.2 Analogues of edelfosine In view of the remarkable effects of edelfosine on cancer cells [122], its action as a proapoptotic agent [123][124] and its effect on lipid raft [125][126] or its action against leishmania [127][128], the synthesis of analogues of edelfosine

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• acid sequence in the cyclic peptide backbone but differing only by the length of aliphatic fatty acid side chains. When tested against Trypanosoma brucei subsp. brucei strain GUTat 3.1 and Leishmania donovani (Laveran and Mesnil) Ross (D10), digyalipopeptide A (1) gave IC50 values of 12.89 µM (suramin

• neglected parasite. In the presence of RAW 264.7 cell lines, compound 1 was particularly selective towards Leishmania donovani (Laveran and Mesnil) Ross (D10) with an SI value of 14.71. The bioactivity studies conducted confirm the role of these cyclic lipopeptides as defense chemicals in their natural

• environment and their ability to be biologically active across different species. Keywords: Leishmania; lipopeptides; molecular networking; sequence tagging; trypanosomes; Introduction Microbes belonging to the genus Bacillus are mainly Gram-positive with only a few examples characterized as Gram-negative

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• the purealidin bromotyrosine structure class, however, quorum sensing inhibition and antifouling activities against several strains of bacteria and microalgae appears in the literature [33][34], while HIV-1 replication inhibition and anti-Leishmania and Plasmodium activity has also been recorded [35

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• in vitro and in vivo against Leishmania donovani, which causes visceral and cutaneous leishmaniasis. It has been observed that the prodrugs improved efficacy when compared to buparvaquone. Parvaquone (14) is a naphthoquinone with antitheilerial properties that is commercialized for the treatment of

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• antiparasitic study of brevipolides C, G, H, and J (3, 7, 8, and 10) and the IC50 (mM) data obtained are summarized in Table 3 [5]. These compounds demonstrated varying activity levels against multiple Leishmania strains, Trypanosoma cruzy, Plasmodium falciparum, and Giardia lamblia (Table 3, entries 1–8

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• each year in predominately underdeveloped countries. The treatment of the disease is severely underdeveloped due to the ability of the Leishmania pathogen to evade and abate immune responses. In an effort to develop anti-leishmaniasis vaccines and adjuvants, novel carbohydrate-based probes were made to

• feasible targets for both parasite detection and vaccine development [3]. Leishmania, an obligate intracellular parasite with varying surface glycoconjugates, infects an estimated 12 million people worldwide and has 350 million people at risk in endemic areas (predominately in underdeveloped countries

• pathogenesis, the parasite infects and propagates in immune cells, the very cells responsible for host protection. Through a range of mechanisms not entirely understood, Leishmania subverts activation of antimicrobial (nitric oxide) and cytokine inducible functions that initiate effective immunity [5]. There

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• artemisinine, thapsigargin, and parthenolide are used nowadays for the treatment of malaria and cancer and have shown antileishmanial activities [13][14]. About two million new cases of Leishmania infection are considered to occur every year in tropical countries including Brazil. Today no effective vaccine

• for the prevention of Leishmania diseases exist, whereas current chemotherapy is ineffective due to the high toxicity, the emergence of drug resistance, and the high cost of treatment, among others [15][16][17]. Consequently, infected people betake of medicinal plants as an alternative to provide

• sesquiterpenes including a rare skeleton (trixane). Only few of them were described from the genus Jungia along with polyacetylenes, coumarins and flavonoids [6][7][24][25][26]. Globally, the tested glycosylated sesquiterpenes displayed no or weak activity against Leishmania strains, and displayed no

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• . Activity of hybrid compounds 28 and 29 against VZV and CMV viruses, as well as against Leishmania donovani promastigotes, was evaluated. Unfortunately, none of them showed any activity up to 250 μM. 3. The Ugi reaction The Ugi reaction allows for a facile synthesis of a bisamide from a ketone (or an

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• activity was detected. Additionally, the peptide 1 was tested against several parasites (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, Plasmodium falciparum) being the causative agents of the neglected tropical diseases [18] sleeping sickness, leishmaniasis and malaria

Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes

• Ricardo A. W. Neves Filho,
• Bernhard Westermann and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2011, 7, 1504–1507, doi:10.3762/bjoc.7.175

• heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1]. Keywords: diversity oriented synthesis; julocrotine; leishmania; Mitsunobu reaction; Ugi reaction; Introduction Julocrotine (1) is a natural glutarimide alkaloid isolated from several plants of the genus Croton [2][3][4

• interestingly, it was found to inhibit the growth of promastigote and amastigote forms of the protozoan Leishmania amazonensis (L.) with no cytotoxicity against the host cell [8]. This parasite causes cutaneous leishmaniasis, a neglected disease that affects more than 12 million people in tropical countries [9

• Leishmania amazonensis (L.). It could be helpful to elucidate the to-date unknown mode of action of this natural product in the parasite. Conclusion In summary, a highly efficient method to synthesize (−)-julocrotine (1) in three steps from Cbz-glutamine 2 was developed. The approach affords the natural

Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

• Kiymet Berkil Akar,
• Osman Cakmak,
• Orhan Büyükgüngör and
• Ertan Sahin

Beilstein J. Org. Chem. 2011, 7, 1036–1045, doi:10.3762/bjoc.7.118

• Leishmania species [12]. Results and Discussion A solution of hexabromide 6 in dry methanol was treated with two equivalents of silver perchlorate at room temperature for two days in the dark. The reaction resulted in the formation of dimethoxy compounds 7 and 8 in a ratio of 37:63 as assigned by 1H NMR

Symmetrical and unsymmetrical α,ω-nucleobase amide-conjugated systems

• Sławomir Boncel,
• Maciej Mączka,
• Krzysztof K. K. Koziol,
• Radosław Motyka and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2010, 6, No. 34, doi:10.3762/bjoc.6.34

• medium antiprotozoal activity; thus I and III exhibited growth inhibition of parasities – Leishmania donovani and Plasmodium falciparum – at levels of 21.4 and 30.6%, respectively [2]. Compound II reduced the Plasmodium falciparum population by only 17.4%, although it was the most active derivative