19836-78-3Relevant articles and documents
Design, synthesis and antimalarial evaluation of novel thiazole derivatives
Bueno, José María,Carda, Miguel,Crespo, Benigno,Cu?at, Ana Carmen,de Cozar, Cristina,León, María Luisa,Marco, J. Alberto,Roda, Nuria,Sanz-Cervera, Juan F.
, p. 3938 - 3944 (2016)
As part of our medicinal chemistry program's ongoing search for compounds with antimalarial activity, we prepared a series of thiazole analogs and conducted a SAR study analyzing their in vitro activities against the chloroquine-sensitive Plasmodium falciparum 3D7 strain. The results indicate that modifications of the N-aryl amide group linked to the thiazole ring are the most significant in terms of in vitro antimalarial activity, leading to compounds with high antimalarial potency and low cytotoxicity in HepG2 cell lines. Furthermore, the observed SAR implies that non-bulky, electron-withdrawing groups are preferred at ortho position on the phenyl ring, whereas small atoms such as H or F are preferred at para position. Finally, replacement of the phenyl ring by a pyridine affords a compound with similar potency, but with potentially better physicochemical properties which could constitute a new line of research for further studies.
Self-immolative polymers containing rapidly cyclizing spacers: Toward rapid depolymerization rates
Chen, Eric K. Y.,McBride, Ryan A.,Gillies, Elizabeth R.
, p. 7364 - 7374 (2012)
Self-immolative polymers containing 4-hydroxybenzyl alcohol alternating with either N-methylaminoethanol or 2-mercaptoethanol spacers were synthesized and demonstrated to controllably depolymerize in response to the cleavage of a stabilizing end-cap from
5-Aryl-2-oxo-1,2,4-oxathiazoles as Cyclocarbonylating Agents for 2-Aminoalcohols and 1,2-Diamines
Rajca, Andrzej,Grobelny, Damian,Witek, Stanislaw,Zbirovsky, Miroslav
, p. 1032 - 1033 (1983)
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Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene
Petzold, Daniel,Nitschke, Philipp,Brandl, Fabian,Scheidler, Veronica,Dick, Bernhard,Gschwind, Ruth M.,K?nig, Burkhard
supporting information, p. 361 - 366 (2018/11/23)
The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.
Combining Low-Pressure CO2 Capture and Hydrogenation to Form Methanol
Khusnutdinova, Julia R.,Garg, Jai Anand,Milstein, David
, p. 2416 - 2422 (2015/04/14)
This paper describes a novel approach to CO2 hydrogenation, in which CO2 capture with aminoethanols at low pressure is coupled with hydrogenation of the captured product, oxazolidinone, directly to MeOH. In particular, (2-methylamino)ethanol or valinol captures CO2 at 1-3 bar in the presence of catalytic Cs2CO3 to give the corresponding oxazolidinones in up to 65-70 and 90-95% yields, respectively. Efficient hydrogenation of oxazolidinones was achieved using PNN pincer Ru catalysts to give the corresponding aminoethanol (up to 95-100% yield) and MeOH (up to 78-92% yield). We also have shown that both CO2 capture and oxazolidinone hydrogenation can be performed in the same reaction mixture using a simple protocol that avoids intermediate isolation or purification steps. For example, CO2 can be captured by valinol at 1 bar with Cs2CO3 catalyst followed by 4-isopropyl-2-oxazolidinone hydrogenation in the presence of a bipy-based pincer Ru catalyst to produce MeOH in 50% yield after two steps.
