4286-55-9Relevant articles and documents
Supramolecular organogels based on mesogenic 2,7-difunctionalized triphenylenes as a simple system for water content assessment in light alcohols
Vadra, Nahir,Huck-Iriart, Cristián,Giovanetti, Lisandro J.,Di Chenna, Pablo H.,Cukiernik, Fabio D.
, p. 2423 - 2434 (2020)
A series of three triphenylene compounds-denoted 2,7-THTP-DiCnOH-bearing four hexyloxy ancillary chains and two variable-length alkoxy chains terminally functionalized with hydroxyl groups have been synthesized and characterized. The studied compounds exhibited thermotropic mesomorphism; the detailed nature of the mesophases was found to depend on the relative positions of the terminal functional groups relative to the crown formed by the ancillary chains. All the studied compounds were able to act as supramolecular gelators in a variety of alcohols; their organogelating ability has been rationalized in terms of physicochemical parameters like the dielectric constant, which allowed us to establish very precise predictive "solvent gelation windows" for each compound. Remarkably stable gels have been detected for 2,7-THTP-DiC6OH in methanol. As a proof of principle, we present the water sensing performance as a rapid method for the assessment of water content in alcohol samples based on the influence that the water content exerts on the gels' thermostability.
Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica
Busta, Lucas,Budke, Jessica M.,Jetter, Reinhard
, p. 38 - 49 (2016)
The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40-C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed.
INSECTICIDAL AMIDES. SYNTHESIS OF NATURAL 2(E),4(E),10(E)-PIPERCIDE, ITS 2(E),4(E),10(Z)-STEREOMER, AND RELATED ISOBUTYLAMIDES
Crombie, Leslie,Denman, Raymond
, p. 4267 - 4270 (1984)
Natural pipercide and its 2(E),4(E),10(Z)-stereomer are synthesised, the latter having superior insecticidal potency and knock down. 10,11-Dihydro- and 10,11-dehydropipercides are also prepared.
Design, synthesis and antiparasitic evaluation of click phospholipids
Afroudakis, Pantelis,Barrias, Emile,Bifeld, Eugenia,Borsari, Chiara,Calogeropoulou, Theodora,Clos, Joachim,Costi, Maria Paola,Ellinger, Bernhard,Fotopoulou, Theano,Fragiadaki, Irini,Georgikopoulou, Kalliopi,Gul, Sheraz,Hachenberg, Julia,Kuzikov, Maria,Magoulas, George E.,Prousis, Kyriakos C.,Roussaki, Marina,Santarem, Nuno,Scoulica, Effie,Tejera Nevado, Paloma,da Silva, Anabela Cordeiro,de Souza, Wanderley
, (2021/07/26)
A library of seventeen novel ether phospholipid analogues, containing 5-membered heterocyclic rings (1,2,3-triazolyl, isoxazolyl, 1,3,4-oxadiazolyl and 1,2,4-oxadiazolyl) in the lipid portion were designed and synthesized aiming to identify optimised miltefosine analogues. The compounds were evaluated for their in vitro antiparasitic activity against Leishmania infantum and Leishmania donovani intracellular amastigotes, against Trypanosoma brucei brucei and against different developmental stages of Trypanosoma cruzi. The nature of the substituents of the heterocyclic ring (tail) and the oligomethylene spacer between the head group and the heterocyclic ring was found to affect the activity and toxicity of these compounds leading to a significantly improved understanding of their structure–activity relationships. The early ADMET profile of the new derivatives did not reveal major liabilities for the potent compounds. The 1,2,3-triazole derivative 27 substituted by a decyl tail, an undecyl spacer and a choline head group exhibited broad spectrum antiparasitic activity. It possessed low micromolar activity against the intracellular amastigotes of two L. infantum strains and T. cruzi Y strain epimastigotes, intracellular amastigotes and trypomastigotes, while its cytotoxicity concentration (CC50) against THP-1 macrophages ranged between 50 and 100 μM. Altogether, our work paves the way for the development of improved ether phospholipid derivatives to control neglected tropical diseases.
Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues
Yoshida, Masahito,Saito, Koya,Kato, Hikaru,Tsukamoto, Sachiko,Doi, Takayuki
supporting information, p. 5147 - 5150 (2018/03/26)
The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.
