In: Organic & Biomolecular Chemistry, 2020, vol. 18, no. 40, p. 8034–8057
Metathesis reactions are one of the most reliable and prevalent ways of creating a C– C bond in synthesis. Photochemical variants exist, and they have proven extremely useful for the construction of complex molecules, from natural products to Möbius rings. A variety of starting materials can undergo photometathesis reactions, including alkenes, alkynes, carbonyls, thiocarbonyls, and...
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In: ACS Sensors, 2020, vol. 5, no. 8, p. 2338–2343
Reactions templated by nucleic acids are currently at the heart of applications in biosensing and drug release. The number of chemical reactions selectively occurring only in the presence of the template, in aqueous solutions, and at room temperature and able to release a chemical moiety is still very limited. Here, we report the use of the p-nitrophenyl carbonate (NPC) as a new reactive...
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In: The Journal of Organic Chemistry, 2020, vol. 85, no. 11, p. 7611–7619
Hydrogenolysis of tertiary benzylic alcohols on palladium on carbon (Pd/C) generally proceeds with inversion of configuration. However, little is known about the hydrogenolysis mechanism of primary and secondary benzylic alcohols. Literature precedents suggest that these substrates may interact differently with the catalyst. To study the mechanism, we synthesized a pair of deuterated...
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In: CHIMIA International Journal for Chemistry, 2019, vol. 73, no. 9, p. 720–723
Photochemical reactions are often presented as intrinsically environmentally friendly ('green'). This may be indeed the case, but only in particular circumstances. This short essay comments on various aspects of the greenness of photochemical reactions, both in a historical (when only mercury-based hard UV light sources were available) and a current (with the recent introduction of LED...
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In: The Journal of Organic Chemistry, 2019, vol. 84, no. 12, p. 7776–7785
A self-immolative dendritic structure was synthesized. It is based on phenol derivatives with three hydroxymethyl arms at both ortho and para positions of the core unit, potentially releasing up to 27 leaving groups in a third-generation dendrimer. The triggering event is the photolysis of a photosentive ortho-nitrobenzyl group. In doing so, we expected to transform a weak chemical or...
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In: Natural Product Research, 2019, p. 1-9
A new cerebroside, Contortamide (1) together with nine known compounds spegatrine (2), affinisine (3), Nb-methylaffinisine (4), ursolic acid (5), α-amyrin (6), bauerenol acetate (7), lupeol (8), betulinic acid (9) and β-sitosterolglycoside (10) were isolated from the trunk bark of Tabernaemontana contorta Stapf. The new compound 1 showed significant activity against Caco-2 colon cancer...
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In: Natural Product Research, 2018, vol. 32, no. 16, p. 1971-1976
The chemical investigation of the extract of the dried leaves of Rauvolfia caffra (Sond) (synonym Rauvolfia macrophylla) (Apocynaceae) led to isolation of a new glycoside derivative, rauvolfianine (1) as well as six known compounds: oleanolic acid (2), sitosterol-3-O-β-D-glucopyranoside (3), betulinic acid (4), vellosimine (5), sarpagine (6) and...
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In: RSC Advances, 2018, vol. 8, no. 42, p. 23881–23890
Sulfur Mustard (SM) is a blistering agent used as a chemical weapon. Glutathione (GSH) is involved in the β-lyase degradation pathway of SM and recently, bioadducts between SM and GSH were observed in vitro. While these bioadducts have never been isolated from in vivo tests or real poisoning with SM, they could be of interest as potential future biomarkers for the retrospective validation of...
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In: Pharmaceutical Biology, 2018, vol. 56, no. 1, p. 318-324
Context: The roots of Lophira lanceolata Van Tiegh. Ex Keay (Ochnaceae) have numerous medicinal values in the Central African region. Even though the MeOH extract of the roots has shown antimycobacterial activities, the constituents responsible for this inhibitory activity remain unknown.Objective: Phytochemical investigation of the MeOH root extract of L. lanceolata and determination of the ...
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In: European Journal of Organic Chemistry, 2018, vol. 2018, no. 3, p. 316–328
The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving...
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